Petrov, Alexander P. et al. published their research in Talanta in 2020 | CAS: 879-37-8

Indole-3-acetamide (cas: 879-37-8) belongs to indole derivatives. In addition to tryptophan, indigo, and indoleacetic acid, numerous compounds obtainable from plant or animal sources contain the indole molecular structure. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.Synthetic Route of C10H10N2O

Database of free solution mobilities for 276 metabolites was written by Petrov, Alexander P.;Sherman, Lindy M.;Camden, Jon P.;Dovichi, Norman J.. And the article was included in Talanta in 2020.Synthetic Route of C10H10N2O This article mentions the following:

Although databases are available that provide mass spectra and chromatog. retention information for small-mol. metabolites, no publicly available database provides electrophoretic mobility for common metabolites. As a result, most compounds found in electrophoretic-based metabolic studies are unidentified and simply annotated as “features”. To begin to address this issue, the authors analyzed 460 metabolites from a com. library using capillary zone electrophoresis coupled with electrospray mass spectrometry. To speed anal., a sequential injection method was used wherein six compounds were analyzed per run. An uncoated fused silica capillary was used for the anal. at 20掳 with a 0.5% (volume/volume) formic acid and 5% (volume/volume) methanol background electrolyte. A Prince autosampler was used for sample injection and the capillary was coupled to an ion trap mass spectrometer using an electrokinetically-pumped nanospray interface. The authors generated mobility values for 276 metabolites from the library (60% success rate) with an average standard deviation of 0.01 脳 10-8 m2V-1s-1. As expected, cationic and anionic compounds were well resolved from neutral compounds Neutral compounds co-migrated with electroosmotic flow. Most of the compounds that were not detected were neutral and presumably suffered from adsorption to the capillary wall or poor ionization efficiency. In the experiment, the researchers used many compounds, for example, Indole-3-acetamide (cas: 879-37-8Synthetic Route of C10H10N2O).

Indole-3-acetamide (cas: 879-37-8) belongs to indole derivatives. In addition to tryptophan, indigo, and indoleacetic acid, numerous compounds obtainable from plant or animal sources contain the indole molecular structure. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.Synthetic Route of C10H10N2O

Referemce:
Indole alkaloid derivatives as building blocks of natural products from聽Bacillus thuringiensis聽and聽Bacillus velezensis聽and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Downstream synthetic route of 879-37-8

879-37-8 Indole-3-acetamide 397, aindole-building-block compound, is more and more widely used in various fields.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.879-37-8,Indole-3-acetamide,as a common compound, the synthetic route is as follows.,879-37-8

Step 6 To a solution of 5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl) oxoacetic acid methyl ester (1.0 g, 4.12 mmol) and indole-3-acetamide (0.8 g, 4.5 mmol) in anhydrous tetrahydrofuran at 0 C. was added a solution of potassium t-butoxide (1M in tetrahydrofuran) (12.4 mL, 12.4 mmol) dropwise over 30 minutes. The mixture was stirred at 0 C. for 2 hours. Concentrated hydrochloric acid (10 mL) was then added and the mixture stirred for 1 hour at room temperature. The mixture was then diluted with ethyl acetate (200 mL), washed twice with water (50 mL), and saturated aqueous sodium chloride solution (50 mL) and the organic layer dried over anhydrous sodium sulfate. The residue was purified by silica gel chromatography, eluting with ethyl acetate/hexanes (1:4) to afford 3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-4-(1H-indol-3-yl) pyrrole-2,5-dione as a bright red solid (1.2 g, 80%). 1H NMR (CDCl3) 400 MHz delta: 8.5 (brs, 1H), 7.78 (s, 1H), 7.63 (d, 1H, J=2.8 Hz), 7.44 (s, 1H), 7.35 (d, 1H, J=8 Hz), 7.16 (d, 1H, J=8.4 Hz), 7.11 (t, 1H, J=7.6 Hz), 6.86 (t, 1H, J=7.6 Hz), 6.80 (d, 1H, J=7.2 Hz), 6.64 (t, 1H, J=8 Hz), 6.57 (d, 1H, J=8 Hz), 4.2 (t, 2H, J=6 Hz), 2.96 (t, 2H, J=6 Hz), 2.24 (m, 2H).

879-37-8 Indole-3-acetamide 397, aindole-building-block compound, is more and more widely used in various fields.

Reference:
Patent; ArQule, Inc.; Kyowa Hakko Kirin Co., Ltd.; Chan, Thomas C.K.; France, Dennis S.; Ishii, Kenichi; Pucci, Paolo; (69 pag.)US2015/328208; (2015); A1;,
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Analyzing the synthesis route of 879-37-8

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879-37-8, Indole-3-acetamide is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

879-37-8, EXAMPLE 1 3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-4-(1H-indol-3-yl)pyrrole-2,5-dione [0441] To a 0 C. solution of 5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)oxoacetic acid methyl ester (0.5 g, 2.06 mmol) and indole-3-acetamide (0.394 g, 2.26 mmol) in 10 mL of tetrahydrofuran was added dropwise potassium tert-butoxide (16.4 mL, 16.4 mmol, 1 M in tetrahydrofuran). Following 2 hours at 0 C., 5.0 mL of concentrated hydrochloric acid was added and the reaction mixture stirred at room temperature for 1 more hour. The mixture was diluted with 100 mL of ethyl acetate, and the organic layer washed with water (2×25 mL), saturated aqueous sodium chloride (25 ml), dried over sodium sulfate, filtered and concentrated in vacuo. The residue was subjected to silica gel chromatography, eluting with a gradient of dichloromethane containing from 1-5% methanol. Fractions containing product were combined and concentrated under reduced pressure to provide 0.598 g (79%) of the title compound as a red solid. [0442] MS (IS, m/z) C23H17N3O2 (M++1)=368.

As the paragraph descriping shows that 879-37-8 is playing an increasingly important role.

Reference:
Patent; Al-Awar, Rima Salim; Hecker, Kyle Andrew; Ray, James Edward; Huang, Jianping; Joseph, Sajan; Li, Tiechao; Paal, Michael; Rathnachalam, Radhakrishnan; Shih, Chuan; Waid, Philip Parker; Zhou, Xun; Zhu, Guoxin; US2003/229026; (2003); A1;,
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Brief introduction of 879-37-8

As the paragraph descriping shows that 879-37-8 is playing an increasingly important role.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.879-37-8,Indole-3-acetamide,as a common compound, the synthetic route is as follows.,879-37-8

To a solution of 5, 6-dihydro-4H-pyrrolo [3,2,1-//] quinolin-1-yl) oxoacetic acid methyl ester (1.0 g, 4.12 mmol) and indole-3-acetamide (0.8 g, 4.5 mmol) in anhydrous tetrahydrofuran at O0C was added a solution of potassium t-butoxide (IM in tetrahydrofuran) (12.4 ml, 12.4 mmol) dropwise over 30 minutes. The mixture was stirred at 0 C for 2 hours. Concentrated hydrochloric acid (10 ml) was then added and the mixture stirred for 1 hour at room temperature. The mixture was then diluted with ethyl acetate (200 ml), washed twice with water (50 ml), and saturated aqueous sodium chloride solution (50 ml) and the organic layer dried over anhydrous sodium sulfate. The residue was purified by silica gel chromatography, eluting with ethyl acetate/hexanes (1:4) to afford 3-(5,6-dihydro-4H- pyrrolo [3,2,1-?)’] quinolin-l-yl)-4(lH-indol-3-yl) pyrrole-2, 5-dione as a bright red solid (1.2 g, 80 %). 1H NMR (CDCl3) 400 MHz delta: 8.5(brs, IH), 7.78(s, IH), 7.63(d, IH, J=2.8 Hz), 7.44(s, IH), 7.35(d, IH, J=8 Hz), 7.16(d, IH, J=8.4 Hz), 7.1 l(t, IH, J=7.6 Hz), 6.86 (t, IH, J=7.6 Hz), 6.80(d, IH, J=7.2 Hz),6.64(t, IH, J=8 Hz), 6.57(d, IH, J=8 Hz), 4.2(t, 2H, J=6 Hz), 2.96(t, 2H, J=6 Hz), 2.24(m, 2H).

As the paragraph descriping shows that 879-37-8 is playing an increasingly important role.

Reference:
Patent; ARQULE, INC.; WO2006/86484; (2006); A1;,
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

New learning discoveries about 879-37-8

879-37-8 Indole-3-acetamide 397, aindole-building-block compound, is more and more widely used in various fields.

879-37-8, Indole-3-acetamide is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,879-37-8

Indole amide (1d) (2.09 g, 12 mmol) and 5-bromopyrimidine (2.48 g, 15.6 [MMOL)] were dissolved in DMF (12 mL), and potassium carbonate (1.82 g, 13.2 [MMOL)] and [CUO] (477 mg, 6.0 [MMOL)] were added and the reaction was stirred at 165 [C] for 18 h. The volatiles were removed under vacuo and the residue was partitioned between [CHC13] (300 mL) and water (150 mL). Two layers were separated and the aqueous layer was extracted with [CHC13] (100 mL). The combined organic layers were washed with water, brine and then filtered through Celite to remove insolubles. The filtrate was evaporated under vacuo to ca. 30 mL of volume, to which were added EtOAc (50 mL) and hexane (20 mL). The mixture was cooled to 0 [C,] and the resulting solid was collected by filtration to give 1.30 g of Compound 4a as a light yellow [SOLID.’H] NMR (CD30D) 8 9.13 (s, 1 H), 9.10 (s, 2 H), 7.69 (d, J = 8.0 Hz, 1 H), 7.60 (d, J = 8.2 Hz, 1 H), 7.53 (s, 1 H), 7.30-7. 22 (m, 2 H), 3.74 (s, 2 H). ES-MS m/z 253 [(MH+).] The a-keto ester 1c (78 mg, 0.28 [MMOL)] and amide Compound 4a (50 g, 0.2 [MMOL)] were combined in dry THF (3 mL) under argon and cooled in an ice bath as 1 M potassium t-butoxid in THF (0.8 mL, 0.8 [MMOL)] was added dropwise. The reaction mixture was stirred at 0 [C] for 40 min, then rt for 80 min. The mixture was cooled back to 0 [C] while 12 N [HCI] (1 mL) was slowly added. After stirred at rt for 5 min, the mixture was diluted with H20 (5 mL), basified with 3N [NAOH,] and extracted with EtOAc. The organic layers were combined and washed with brine, dried [(NA2SO4)] and evaporated in vacuo to give a crude solid. The crude product was purified by reverse-phase HPLC using a gradient of 10% to 90% [ACETONITRILE/WATER] (containing 0.2% TFA) to afford Compound 11 (32 mg) as a red-orange solid (TFA [SALT).’H] NMR (DMSO-d6) [8] 9.26 (s, 1 H), 9.07 (s, 2 H), 8.74 (s, 1 H), 8.66 (d, J = 3.6 Hz, [1] H), 8.14 (s, 1 H), 8.08 (m, 1 H), 8.05 (s, 1 H), 7.66 (dd, [J = 4.] 7,8. 2 Hz, 1 H), 7.61 (d, [J =] 8.3 Hz, 1 H), 7.53 (d, J = 8.3 Hz, [1] H), 7.20 (m, 2 H), 7.12 (s, 1 H), 7.09 (s, [1H),] 6.96 (m, 2H). ES-MS m/z 483 (MH+).

879-37-8 Indole-3-acetamide 397, aindole-building-block compound, is more and more widely used in various fields.

Reference:
Patent; Janssen Pharmaceutica N.V.; WO2003/104222; (2003); A1;,
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Some tips on 879-37-8

The synthetic route of 879-37-8 has been constantly updated, and we look forward to future research findings.

879-37-8,879-37-8, Indole-3-acetamide is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To compound C, indole-3-acetamide (104.71 g) and THF (1428 mL) were added at about 15 C. to about 35 C. under a nitrogen atmosphere. The resulting solution was added dropwise in the range of about 20 C. to about 32 C. over about 30 minutes or longer under a nitrogen atmosphere to a 1 M solution of potassium tert-butoxide in THF (1382.5 mL) further diluted with THF (420 mL). The reaction solution was stirred at about 20 C. to about 32 C. for about 2 hours. Then, 12 M hydrochloric acid (312 mL) was added dropwise at about 50 C. or lower, and the mixture was stirred at about 40 C. to about 50 C. for about 1 hour. After the completion of reaction, water (465 mL) and 28% ammonia water (465 mL) were added to the reaction solution, and the mixture was stirred at about 20 C. to about 32 C. for about 30 minutes or longer and then separated into aqueous and organic layers. The aqueous layer was removed. The organic layers containing compound B were combined and concentrated to about 2100 mL under a reduced pressure at an internal temperature of about 60 C. or lower. Ethanol (4095 mL) was added to the concentrated solution containing compound B. The resulting solution containing compound B was further concentrated to about 2100 mL under a reduced pressure at about 60 C. or lower, and then, ethanol (1050 mL) was added. The solution was concentrated to about 2100 mL under a reduced pressure at about 60 C. or lower to adjust the THF concentration to 2% or less. The concentrated solution obtained was cooled to about 20 C. to about 30 C., and water (2100 mL) was added dropwise over about 1 hour or longer. The resulting mixture containing compound B was stirred at about 20 C. to about 30 C. for 1 hour. The deposited crystals of compound B were collected by filtration and washed with a 50% aqueous ethanol solution (1050 mL). The crystals of compound B were dried in vacuum at about 45 C. to about 55 C. for about 12 hours or longer (178.7 g, yield: 80.9% (calculated based on indole-3-acetamide)). The crystals of compound B thus obtained can be used directly in next step. The crystals of compound B may be further purified as follows: methylene chloride (750 mL) was added to the crystals of compound B (150.0 g), and the mixture was stirred at about 15 C. to about 25 C. for about 2 hours or longer. To this suspension containing compound B, heptane (750 mL) was added dropwise at about 15 C. to about 25 C. over about 1 hour or longer, and the mixture was stirred at about 15 C. to about 25 C. for about 2 hours or longer. The deposited crystals of compound B were collected by filtration and washed with a mixed solvent of methylene chloride and heptane (mixing ratio: 1/1) (450 mL). The crystals of compound B were dried in vacuum at about 45 C. to about 55 C. for about 12 hours or longer (146.1 g, yield from crystals before purification: 97.4%).

The synthetic route of 879-37-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ARQULE, INC.; Nakamura, Yoshitaka; Ooyama, Jo; US2013/281699; (2013); A1;,
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

New learning discoveries about 879-37-8

879-37-8 Indole-3-acetamide 397, aindole-building-block compound, is more and more widely used in various fields.

879-37-8, Indole-3-acetamide is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

879-37-8, EXAMPLE 134 S-3-(5-hydroxymethyl-4,5-dihydro-6H-[1,4]diazepino[6,7,1-hi]indol-1-yl)-4-(1H-indol-3-yl)pyrrole-2,5-dione [0796] To a suspension of indole-3-acetamide (0.501 g, 2.34 mmol) and (S-6-(tert-butoxycarbonyl)-5-(tert-Butoxy)methyl-4,5-dihydro-6H-[1,4]diazepino[6,7,1-hi]indol-1-yl)oxo-acetic acid methyl ester (1.00 g, 2.34 mmol) in tetrahydrofuran (10 ml) at 0 C. was added potassium tert-butoxide (9.36 mmol, 9.36 ml, 1M in THF). The reaction was allowed to warm to 20-24 C. and stirred for 15 hours. The reaction was quenched with concentrated hydrochloric acid (5 ml) and stirred for 30 minutes. The reaction was then basified with 5N sodium hydroxide and extracted with ethyl acetate. The organic phase was washed with saturated aqueous sodium chloride, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was dissolved in ethanol (10 ml) and 5N hydrochloric acid (10 ml) was added. The reaction mixture was then stirred for 30 minutes, cooled to room temperature and concentrated under reduced pressure. The residue was made basic with 5N sodium hydroxide and extracted with ethyl acetate. The organic phase was washed with saturated aqueous sodium chloride, dried over magnesiun sulfate, filtered and concentrated under reduced pressure. The residue was then subjected to silica gel chromatography, eluting with ethyl acetate:methanol (9:1). Fractions containing the desired compound were combined and concentrated under reduced pressure to provide 0.60 g (65%) of the title compound as a red solid. [0797] MS (ES, m/z) (M+1)=413.0.

879-37-8 Indole-3-acetamide 397, aindole-building-block compound, is more and more widely used in various fields.

Reference:
Patent; Al-Awar, Rima Salim; Hecker, Kyle Andrew; Ray, James Edward; Huang, Jianping; Joseph, Sajan; Li, Tiechao; Paal, Michael; Rathnachalam, Radhakrishnan; Shih, Chuan; Waid, Philip Parker; Zhou, Xun; Zhu, Guoxin; US2003/229026; (2003); A1;,
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Simple exploration of 879-37-8

The synthetic route of 879-37-8 has been constantly updated, and we look forward to future research findings.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.879-37-8,Indole-3-acetamide,as a common compound, the synthetic route is as follows.

879-37-8, Example 1The present example describes the preparation of 3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-4-(1H-indol-3-yl)pyrrole-2,5-dione.Lilolidine [CAS 102280-97-7] (70 kg) (Compound 4 in Scheme I) was charged to an appropriately cleaned and dry reactor vessel followed by methyl tert-butyl ether (MTBE) (375 kg). Lilolidine may be purchased commercially or prepared as described in U.S. Patent Application Publication No. 2006/0223760. The resulting batch was agitated for a minimum of 10 minutes at 15-25 C. A solution of oxalyl chloride (56.6 kg) in MTBE (370 kg) was prepared in a separate vessel. The lilolidine solution was then added to the oxalyl chloride solution at such a rate to maintain the temperature below 32 C. The vessel was rinsed with additional MTBE (162 kg) and added to the reaction mixture. The batch was stirred at 15-32 C. for a minimum of two hours prior to analysis by HPLC. When the reaction was determined to be complete, methanol (90 kg) was added, and the batch was stirred for a minimum of two hours. When the reaction was determined to be complete by HPLC analysis, the batch was distilled to approximately 80 gallons. It is not necessary to isolate the intermediate 5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl) oxoacetic acid methyl ester (Compound 5 in Scheme I). Tetrahydrofuran (THF) (840 kg) was added to the batch and the volume was again reduced to approximately 80 gallons by distillation. This solvent swap process was continued until the amount of MTBE present in the batch was <1% by weight. A new vessel was charged with indole-3-acetamide [CAS 879-37-8] (61.3 kg) (Compound 5a in Scheme I) followed by THF (840 kg). The resulting solution was then charged to the batch at a rate such that the temperature was maintained at 15-25 C. The vessel containing the solution of indole-3-acetamide was rinsed with THF (140 kg), and the rinse was added to the batch. The empty vessel was then charged with potassium tert-butoxide solution (1.6 M in THF, 581 kg) and THF (350 kg). The solution was also added to the batch, and the resulting solution was stirred at 20-32 C. for a minimum of three hours. When the starting material had been consumed as confirmed by HPLC analysis, aqueous HCl (conc., 273 kg) was added at such a rate that the temperature was maintained below 50 C. The batch was stirred at 40-50 C. for a minimum of 30 minutes.When the reaction had been determined to be complete by HPLC analysis, aqueous ammonium hydroxide solution (conc.) was added, while maintaining the reaction temperature below 40 C., until the pH of the mixture was 9-10. Following the addition of ethyl acetate (EtOAc) (462 kg) and agitation of the batch, the layers were separated. The organic layer was washed with brine (182 kg NaCl and 1022 kg water). The resulting organic solution was distilled to approximately one third of the starting volume. Ethanol (2B, 1120 kg) was added, and the distillation was continued to reduce the batch volume to approximately 240 gallons. Ethanol (2B, 1120 kg) was again added, and the volume reduced to 240 gallons. Water (1400 kg) was then added to the batch to induce precipitation of the product. The batch was agitated for a minimum of two hours, and the solids were isolated by filtration. The solids were then taken up in dichloromethane (DCM) (840 kg), and heptanes (442 kg) were added to purify the product. Following agitation of the batch for at least two hours, the product was isolated by filtration. Following conditioning on the filter, approximately 115 kg (88%) of 3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-4-(1H-indol-3-yl)pyrrole-2,5-dione (Compound 6 in Scheme I) was isolated as a red powder. This conversion of Compound 4 to Compound 6 is shown in Scheme II. The synthetic route of 879-37-8 has been constantly updated, and we look forward to future research findings. Reference:
Patent; ArQule, Inc.; US2011/160242; (2011); A1;,
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles