Month: February 2022

400071-95-6,With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.400071-95-6,5-Bromo-1-methyl-1H-indole-3-carboxylic acid,as a common compound, the synthetic route is as follows.

General procedure: 5-Bromo-1-methyl-indolyl-3-carbohydrazide or 1-methylindolyl-3-carbohydrazide (500 mg, 1.0 eq.) was added to differentindole-3-carboxylic acids (1.87 mmol, 1.0 eq.). To this reactionmixture, 12 vol of polyphosphoric acid was added and heated at90oc over a period of 3.5 he4 h. The reaction mixture was cooled toroom temperature and followed by addition of ice. The PH of theabove reaction mixture was brought to neutral by using sodiumbicarbonate solution. The solid obtained was separated and dried.The crude compoundwas purified by column chromatography withDCM solvent. The solvent was concentrated with rotary undercooling conditions when yellow colored solid was formed. It waswashed with n-hexane and ether solvent to remove non-polar andsemi-polar impurities, which yielded the pure compound in yellowcolor.

400071-95-6 5-Bromo-1-methyl-1H-indole-3-carboxylic acid 11032413, aindole-building-block compound, is more and more widely used in various fields.

Reference：
Article; Sreenivasulu, Reddymasu; Tej, Mandava Bhuvan; Jadav, Surender Singh; Sujitha, Pombala; Kumar, C. Ganesh; Raju, Rudraraju Ramesh; Journal of Molecular Structure; vol. 1208; (2020);,
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

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

343-93-1, 1-(6-Fluoro-1H-indol-3-yl)-N,N-dimethylmethanamine is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Synthesis of the Compound of Formula IIIA detailed synthesis of the compound of Formula III from the compound of Formula II is provided below in Scheme III. Step-Wise Procedure:(6-Fluoro-1H-indol-3-ylmethyl)-dimethylamine (65 g), KCN (31 g), DMF (195 ml) and water (104 ml) were charged to the reactor. The reaction mixture was heated to about 100-105 C. (strong reflux) for about 5-8 hours. The reaction mixture was cooled to 20-25 C. Water (780 ml) and toluene (435 ml) were charged to the reactor and the mixture was stirred vigorously for >2 hours. The organic and aqueous layers were separated. The organic layer was washed with 5% NaHCO3 (6×260 ml), 2M HCl (260 ml), 5% NaHCO3 (260 ml) and 5% NaCl (260 ml), respectively. The organic layer was filtered and concentrated to dryness. MeOH (260 ml) was added and the solution was concentrated to dryness. The compound of Formula III was isolated as a brown oil. Yield: 90%. Purity by HPLC (280 nm): 95%. MS m/z: 193 (M+H)+., 343-93-1

As the paragraph descriping shows that 343-93-1 is playing an increasingly important role.

Reference：
Patent; H. LUNDBECK A/S; US2011/152539; (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

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.31241-19-7,5-Methoxy-2,3,3-trimethyl-3H-indole,as a common compound, the synthetic route is as follows.

Example 1.9 Synthesis of 5-Hydroxy-1,2,3,3-Tetramethyl-3H-Indolium Iodide This compound was prepared by the general synthesis method 1c) from 4.0 g of 5-methoxy-2,3,3-trimethyl-3H-indole, 16 mL of acetic acid and 16 mL of 48% hydrobromic acid solution. Yield (intermediate): 2.45 g of 5-hydroxy-2,3,3-trimethyl-3H-indole (66% of the theoretical). 1.0 g of the intermediate thus obtained was alkylated with 1.66 g of methyl iodide and 10 mL of methanol according to variant 3 under 1b). Yield: 1.36 g of 5-hydroxy-1,2,3,3-tetramethyl-3H-indolium iodide (75% of the theoretical). Melting point: 245-247 C. 1H-NMR (D6-DMSO): delta=1.46 ppm (s, 6H); 2.66 ppm (s, 3H); 3.89 ppm (s, 3H); 6.93 ppm (dd, 3J=9 Hz, 4J=2 Hz, 1H); 7.11 ppm (d, 4J=2 Hz, 1H); 7.67 ppm (d, 3J=9 Hz, 1H); 10.22 ppm (s, exchanges with D2O, 1H). FAB mass spectrum: M+=190.10 (100% rel. intensity), 31241-19-7

31241-19-7 5-Methoxy-2,3,3-trimethyl-3H-indole 11095392, aindole-building-block compound, is more and more widely used in various fields.

Reference：
Patent; Sauter, Guido; Braun, Hans-Juergen; Reichlin, Nadia; US2003/79301; (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

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.5192-03-0,1H-Indol-5-amine,as a common compound, the synthetic route is as follows.

To a stirred suspension of 3,5-dibromopyrazin-2-amine (3.48 g, 13.7 mmol) and IH- indol-5 -amine (2.00 g, 15.0 mmol) in EtOH (3.5 mL) was added diisopropylethylamine [DIEA] (2.60 mL, 15.0 mmol). The resulting mixture was stirred for 48 hr at 800C, after which it was partitioned between EtOAc and H2O. The organic layer was separated, after which it was washed with brine, dried over Na2SO4, filtered, and evaporated in vacuo to yield a residue that was purified via silica gel chromatography eluting with 1: 1 EtOAc :hexanes to yield the title compound (1.75 g, 42%) as a red/brown solid. 1H NMR (DMSO- d6, 300 MHz): delta 10.98 (s, IH), 8.22 (s, IH), 7.83 (s, IH), 7.31-7.28 (m, 3H), 7.19 (d, / = 8.7 Hz, IH), 6.43 (s, 2H), 6.36 (s, IH); HPLC retention time: 2.07 minutes; MS ESI (m/z): 304.2/306.2 (M+l)+, calc. 303, 5192-03-0

The synthetic route of 5192-03-0 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; UNIVERSITY OF ROCHESTER; GELBARD, Harris, A.; DEWHURST, Stephen; GOODFELLOW, Val, S.; WIEMANN, Torsten; WO2010/68483; (2010); A2;,
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

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.399-67-7,7-Fluoro-1H-indole-2-carboxylic acid,as a common compound, the synthetic route is as follows.

General procedure: (5-Chloro-7-fluoro-1H-indole-2-yl)-carboxylic acid (5a) (50 mg, 0.23 mmol), N,N-diisopropylethylamine (82 mul, 0.47 mmol) and 2-(7-Aza-1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (89 mg, 0.23 mmol) were dissolved in 550 mul N,N-dimethylformamide. After stirring for 10 min 4-methyl-piperazin 6a (26 mul, 0.23 mmol) was added and the reaction mixture was stirred for 16 h at 20 C. The solvent was evaporated under reduced pressure and the crude product was purified using chromatography method P1, yielding 37 mg (53%) of the title compound.

399-67-7, The synthetic route of 399-67-7 has been constantly updated, and we look forward to future research findings.

Reference：
Article; Engelhardt, Harald; De Esch, Iwan J.P.; Kuhn, Daniel; Smits, Rogier A.; Zuiderveld, Obbe P.; Dobler, Julia; Mayer, Moriz; Lips, Sebastian; Arnhof, Heribert; Scharn, Dirk; Haaksma, Eric E.J.; Leurs, Rob; European Journal of Medicinal Chemistry; vol. 54; (2012); p. 660 – 668;,
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

16732-69-7, Ethyl 7-bromo-1H-indole-2-carboxylate is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

i) Preparation of ethyl 7-cyclopropyl- 1 H-indole-2-carboxylate (1220) [00217] A mixture of ethyl 7-bromo-1 H-indole-2-carboxylate (300 mg, 1 .12 mmol), cyclopropylboronic acid (192.23 mg, 2.24 mmol), 2M Na2C03 (2.8 ml) and Pd(dppf)CI2 (40.94 mg, 0.06 mmol) in dioxane (9.7 mL) was purged with argon then subjected to microwave irradiation at 100 C for 2 h. The resulting mixture was filtered over celite, rinsing with EtOAc and water. The filtrate was partitioned between EtOAc and 1 M HCI. The aqueous phase was extracted with EtOAc and the combined organic extracts washed with brine, dried over Na2S04, filtered and concentrated under reduced pressure. The residue was taken up in DCM, adsorbed onto silica and purified by flash chromatography (Telos 12 g, EtOAc in heptane, 0- 15%) to give the title compound contaminated with an unknown related impurity. The material was used in the next step without further purification. ii) Preparation of ethyl 7-cyclopropyl-3-iodo- 1 H-indole-2-carboxylate

16732-69-7, The synthetic route of 16732-69-7 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; OXFORD UNIVERSITY INNOVATION LIMITED; BREM, Juergen; RYDZIK, Anna M.; MCDONOUGH, Michael A.; SCHOFIELD, Christopher J.; MORRISON, Angus; HEWITT, Joanne; PANNIFER, Andrew; JONES, Philip; (171 pag.)WO2017/93727; (2017); 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

170147-29-2, tert-Butyl 5-(benzyloxy)-1H-indole-1-carboxylate is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

ferf-Butyl 5-(benzyloxy)-1H-indole-1-carboxylate (5.75 g, 17.8 mmol), preparedaccording to the procedure described for Example 1, step 1, was added to a mixture of10% Pd/C in EtOH. Ammonium formate was added and the reaction stirred for 6 h. Themixture was filtered through Celite under a blanket of argon and the solvents were thenremoved. The residue was purified by flash chromatography to yield 3.5 g of ferf-butyl 5-hydroxy-1H-indole-1-carboxylate (74%). 1H-NMR (DMSO-d6) 5 9.19 (s, 1H), 7.84-7.78 (d,1H), 7.58-7.52 (d, 1H), 6.91 (s, 1H), 7.78-7.69 (m, 1H), 6.65-6.42 (m, 1H), 1.68-1.59 (s,9H).

170147-29-2, 170147-29-2 tert-Butyl 5-(benzyloxy)-1H-indole-1-carboxylate 10663688, aindole-building-block compound, is more and more widely used in various fields.

Reference：
Patent; BAYER PHARMACEUTICALS CORPORATION; WO2005/51957; (2005); 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

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.883526-76-9,1,5-Dimethyl-1H-indole-2-carbaldehyde,as a common compound, the synthetic route is as follows.,883526-76-9

General procedure: 1-methyl-1H-indole-2-carbaldehyde (6.3 mmol) wasdissolved in 20 mL of toluene. (Triphenylphosphoranylidene)-2-propanone (9.4mmol) was added and the mixture was heated at 120 C for 12 h. After cooling,the solvent was removed in vacuo. Then the residue was poured into ether andfiltered to remove Ph3P=O. The filtrate was concentrated and theresidue was purified by column chromatography (petroleum ether : ethyl acetate= 10:1 to 8:1) to give the product 1

883526-76-9 1,5-Dimethyl-1H-indole-2-carbaldehyde 23004693, aindole-building-block compound, is more and more widely used in various fields.

Reference：
Article; Su, Tao; Han, Xiuling; Lu, Xiyan; Tetrahedron Letters; vol. 55; 1; (2014); p. 27 – 30;,
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

1008-07-7, 7-Chloro-1H-indole-3-carbaldehyde is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A solution of Chloro-1H-indole-3-carbaldehyde (100 mg, 0.56 mmol) in MeOH (10 mL) was treated with hydroxylammonium chloride (43 mg, 0.61 mmol), stirred at 23 C for 3 h and treated with nickel(ll) chloride hexahydrate (139 mg, 0.59 mmol). The mixture was cooled to – 78 C, treated portionwise with sodium borohydride (421 mg, 1 1.1 mmol), stirred at -78 C for 1 h before being warmed to RT slowly and stirred until gas evolution had ceased. The mixture was filtered through a syringe filter and evaporated. The residue was dissolved in aqueous 1 % NH3 (30 mL), extracted with EtOAc (3 x 20 mL), dried over anhydrous Na2S04, filtered and evaporated to give the crude ((7-chloro-1 indol-3-yl)methanamine (100 mg, 99%). The product was unstable and was used immediately in the next step without further purification., 1008-07-7

As the paragraph descriping shows that 1008-07-7 is playing an increasingly important role.

Reference：
Patent; EUROPEAN MOLECULAR BIOLOGY LABORATORY; WILL, David William; REID, George; CHARAPITSA, Iryna; LEWIS, Joe; (138 pag.)WO2018/229197; (2018); 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