Month: September 2020

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.16732-73-3,6-Methoxy-1H-indole-2-carboxylic acid,as a common compound, the synthetic route is as follows.

To a 0.1 M stirred solution of an indole-2-carboxylic acid derivative of type (II) in CH2Cl2 are added EDC (1.3 eq), HOBt (1.3 eq), Et3N (1.3 eq) and the amine derivative (A-H, as defined above, 1 eq). The mixture is stirred overnight at room temperature and then poured onto water and extracted with CH2Cl2. The combined organic phases are dried over Na2SO4 and concentrated in vacuo. Flash chromatography or preparative HPLC affords a compound of formula (I).

16732-73-3, 16732-73-3 6-Methoxy-1H-indole-2-carboxylic acid 410327, aindole-building-block compound, is more and more widely used in various.

Reference£º
Patent; Bissantz, Caterina; Grundschober, Christophe; Masciadri, Raffaello; Ratni, Hasane; Rogers-Evans, Mark; Schnider, Patrick; US2008/139548; (2008); 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

10075-50-0, 5-Bromoindole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

5-Bromoindole (1.35 g, 6.9 mmol) was formylated as described for1H-indole-3-carbaldehyde to produce 6-bromo-1H-indole-3-carbaldehyde(1.50 g, 97%) with the exception that the obtained productwas not purified by refluxing in EtOH.5-Bromo-1H-indole-3-carbaldehyde (1.50 g, 6.7 mmol) and NH4OAc(0.52 g, 6.7 mmol) were heated at reflux in CH3NO2 (18 mL, 335mmol) for 45 min, cooled to r.t., and treated with H2O (70 mL). Theproduct was extracted with EtOAc (70 mL), washed with H2O (5 ¡Á 50mL) and NaCl solution (20 mL), and dried over anhydrous Na2SO4. Thesolvent was removed in vacuo to afford 6-bromo-3-[(E)-2-nitrovinyl]-1H-indole (1.72 g, 96%, brownish crystals), which was dried in vacuoand used without further purification.A suspension of 5-bromo-3-[(E)-2-nitrovinyl]-1H-indole (1.72 g, 6.4mmol) and DMAP (0.08 g, 0.64 mmol) in anhydrous THF (7 mL) wastreated with a solution of Boc2O (2.1 g, 9.7 mmol) in anhydrous THF(7 mL) dropwise at 0-5 C over a period of 15 min, stirred at r.t. for 3h, and concentrated in vacuo. The residue was dissolved in CH2Cl2 (50mL), washed with citric acid solution (10%, 20 mL), H2O (20 mL), andconcd NaCl solution (15 mL), and dried over anhydrous Na2SO4. TheCH2Cl2 was evaporated in vacuo and the residue was purified by chromatographyon a column of silica gel (EtOAc-hexane, 6:1) to providetert-butyl 5-bromo-3-[(E)-2-nitrovinyl]-1H-indole-1-carboxylate.Yield: 2.11 g (83% from 5-bromoindole); pale-yellow solid; mp 156-157 C (MeOH); Rf = 0.55 (EtOAc-hexane, 1:8). IR (film): 3130, 2983, 2300 w, 1741 s (CO), 1639, 1509, 1452, 1368,1344, 1240, 1153, 1107, 956, 853, 803, 764, 649, 613, 579 cm-1.1H NMR (400 MHz, DMSO-d6): delta = 8.57 (s, 1 H), 8.33 (d, J = 13.7 Hz,1 H, CH=CHNO2), 8.27 (d, J = 1.9 Hz, 1 H), 8.26 (d, J = 13.7 Hz, 1 H,CH=CHNO2), 8.02 (d, J = 8.8 Hz, 1 H), 7.56 (dd, J = 8.8, 1.9 Hz, 1 H), 1.65(s, 9 H, C(CH3)3).13C NMR (100 MHz, DMSO-d6): delta = 147.89, 136.57, 134.27, 133.94,130.89, 128.52, 128.16, 123.08, 116.83, 116.76, 111.47, 85.53, 27.48(3).MS (EI, 70 eV): m/z (%) = 368/366 (4) [M]+, 312/310 (7) [M – C4H8]+,268/266 (31) [M – C4H8 – CO2]+, 219 (21), 140 (30), 57 (100).Anal. Calcd for C15H15BrN2O4: C, 49.06; H, 4.12; N, 7.63. Found: C,49.19; H, 4.15; N, 7.55.

10075-50-0, The synthetic route of 10075-50-0 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Golantsov, Nikita E.; Festa, Alexey A.; Varlamov, Alexey V.; Voskressensky, Leonid G.; Synthesis; vol. 49; 11; (2017); p. 2562 – 2562;,
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.93957-49-4,3-(4-Fluorophenyl)-1-isopropyl-1H-indole,as a common compound, the synthetic route is as follows.,93957-49-4

The reaction and post treatment were conducted in the same manner as in Example 8 except that acids shown in Table 1 were used instead of phosphorus oxychloride, the amount of glacial acetic acid was 6 mL and conditions shown in Table 1 were used, to obtain methyl trans-3-[3-(4-fluorophenyl)-1-isopropyl-1H-indol-2-yl]acrylate (yellow solid). The results are shown in Table 1.

As the paragraph descriping shows that 93957-49-4 is playing an increasingly important role.

Reference£º
Patent; Sumitomo Chemical Company, Limited; EP1666440; (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

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.52415-29-9,6-Bromoindole,as a common compound, the synthetic route is as follows.

Example 15 1H-Indole-6-carbaldehyde Combine hexane washed potassium hydride (1.3 g, 10.7 mmol) and ether (20 ml). Cool to about 0 C and add a solution of 6-bromo-1H-indole (2.1 g, 10.7 mmol) in ether (5 ml). After 15 min, cool to about -78C and add a solution of t-butyllithium, 1.4 M solution in hexane (14.0 ml, 10.7 mmol). After 10 min, add dimethylformamide (1.7 ml, 20.0 mmol) in ether (5ml). Slowly warm to room temperature and then pour into a ice cold solution of 1M phosphoric acid and extract with EtOAc. Combine the organic layers and wash sequentially with distilled water and brine and then dry (Na2SO4), filter, and concentrated to give a residue. Chromatograph the residue eluting with 9:1 hexane:EtOAc to give the title compound., 52415-29-9

52415-29-9 6-Bromoindole 676493, aindole-building-block compound, is more and more widely used in various.

Reference£º
Patent; ELI LILLY AND COMPANY; Chen, Zhaogen; Cohen, Michael Philip; Fisher, Matthew Joseph; Gillig, James Ronald; McCowan, Jefferson Ray; Miller, Shawn Christopher; Schaus, John Mehnert; Giethlen, Bruno; (141 pag.)EP1859798; (2015); B1;,
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

7254-19-5,With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.7254-19-5,5-Bromo-1H-indole-2-carboxylic acid,as a common compound, the synthetic route is as follows.

A solution of 5-Bromo-1H-indole-2-carboxylic acid (commercial, 10.0 g, 41.6 mmol) in methanol (200 ml) was cooled to 0 C and saturated with HCI (g).. The resulting solution was allowed to warm gradually to room temperature overnight.. The solvent was removed in vacuo and the residue treated with 0.88 ammonia (500 ml).. The resulting solution was extracted with dichloromethane (3-fold 150 ml) and the combined organics dried (magnesium sulphate) and the solvent removed in vacuo to give the required product as a colourless oil (8.35 g).1H NMR (400MHz, CDCl3): delta = 8.96 (1H, bs), 7.83 (1H, s), 7.40 (1H, d), 7.30 (1H, d), 7.14 (1H, s), 3.95 (3H, s). LRMS (electrospray): m/z [M-H]- 252 / 254.

7254-19-5 5-Bromo-1H-indole-2-carboxylic acid 252137, aindole-building-block compound, is more and more widely used in various.

Reference£º
Patent; Pfizer Limited; EP1460064; (2004); 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.1477-49-2,3-Indoleglyoxylic Acid,as a common compound, the synthetic route is as follows.

To a solution of 2-amino-5-aminomethyl-6-(4-methoxy-benzyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridine-3-carboxylic acid tert-butyl ester (209 mg, 0.51 mmol) in dry N,N-dimethylformamide (4 ml) was added 3-indole-glyoxylic acid (141 mg, 0.74 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide, hydrochloride (152 mg, 0.76 mmol), and 1-hydroxy-benzotriazole (100 mg, 0.74 mmol). The mixture was stirred at room temperature for 16 hours, diluted with dichloromethane (100 ml) and washed with water (100 ml), brine (100 ml), dried (MgSO4), filtered, and concentrated in vacuo. The residue was subjected to flash chromatography using a mixture of ethyl acetate/hexanes (2:5) as eluent, which afforded 143 mg (40 %) of 2-amino-5-((2-(1H-indol-3-yl)-2-oxo-acetylamino)methyl)-6-(4-methoxy-benzyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridine-3-carboxylic acid tert-butyl ester as an oil. LC-MS Rt= 2.31 min, m/z: 574.9 [M+H]+. To a solution of 2-amino-5-((2-(1H-indol-3-yl)-2-oxo-acetylamino)methyl)-6-(4-methoxy-benzyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridine-3-carboxylic acid tert-butyl ester (143 mg, 0.25 mmol) in dichloromethane (5 ml) was added imidazol-1-yl-oxo-acetic acid tert-butyl ester (144 mg, 0.75 mmol) and the flask was purged with nitrogen. After 24 hours an additional portion of imidazol-1-yl-oxo-acetic acid tert-butyl ester (169 mg, 0.86 mmol) was added and the reaction mixture allowed stirred for an additional 24 hours. The mixture was then concentrated in vacuo. The residue was purified by flash chromatography using a mixture of ethyl acetate/hexanes (2:5) as eluent, which afforded 101 mg (58 %) of 2-(tert-butyoxyoxalyl-amino)-5-((2-(1H-indol-3-yl)-2-oxo-acetylamino)methyl)-6-(4-methoxy-benzyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridine-3-carboxylic acid tert-butyl ester as a oil. 1H-NMR (CDCl3) delta 9.23 (s, 1H), 9.07 (d, 1H, J = 3.6 Hz), 8.50 (d, 1H, J = 7.6 Hz), 8.15 (d, 1H, J = 4.0 Hz), 7.47 (d, 2H, J = 7.2 Hz), 7.38-7.27 (m, 6H), 6.89 (d, 2H, J = 8.8 Hz), 3.87-3.59 (m, 6H), 3.04 (dd, 2H, J = 23.6 Hz), 2.74 (dd, 2H, J = 22.4 Hz), 1.62 (s, 18H); LC-MS Rt= 2.49 min, m/z: 703 [M+H]+. 2-(tert-Butyoxyoxalyl-amino)-5-((2-(1H-indol-3-yl)-2-oxo-acetylamino)methyl)-6-(4-methoxy-benzyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridine-3-carboxylic acid tert-butyl ester (101 mg, 0.143 mmol) was dissolved in dry tetrahydrofuran (6 ml) and passed through a pipette, plugged with cotton containing Raney 2800 Nickel (0.38 g). The pipette was flushed with dry tetrahydrofuran (6 ml) and the filtrate was concentrated in vacuo. Pd on carbon (10%, 102 mg, source: Avocado) and formic acid (10% in methanol, 5 ml) were added to the flask containing 2-(tert-Butyoxyoxalyl-amino)-5-((2-(1H-indol-3-yl)-2-oxo-acetylamino)methyl)-6-(4-methoxy-benzyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridine-3-carboxylic acid tert-butyl ester. After stirring for 18 hours, the solution was filtered through a pad of celite and concentrated in vacuo. The residue was diluted in ethyl acetate, washed with saturated sodium bicarbonate (2 x 25 ml), brine (2 x 25 ml), dried (MgSO4), filtered and concentrated in vacuo. The residue was subjected to flash chromatography using a mixtureof 10% methanol/dichloromethane as eluent, which afforded 2-(tert-butyoxyoxalyl-amino)-5-((2-(1H-indol-3-yl)-2-oxo-acetylamino)methyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridine-3-carboxylic acid tert-butyl ester. 1H-NMR (CDCl3) delta 9.23 (s, 1H), 9.07 (d, 1H, J= 3.6 Hz), 8.50 (d, 1H, J = 7.6 Hz), 8.15 (d, 1H, J = 4.0 Hz), 7.27 (s, 2H), 7.09 (d, 1H, J = 8.8 Hz), 6.81 (d, 1H, J = 8.8 Hz), 3.79 (s, 1H), 2.29 (s, 1H), 1.62-1.57 (m, 18H), 0.08 (s, 5H); LC-MS: Rt= 2.17 min, m/z: 583 [M+H]+. The above 2-(tert-butyoxyoxalyl-amino)-5-((2-(1H-indol-3-yl)-2-oxo-acetylamino)methyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridine-3-carboxylic acid tert-butyl ester was dissolved in 50% trifluoroacetic acid/dichloromethane (3 ml) and stirred at room temperature for 18 hours. The solvent was removed in vacuo and residual trifluoroacetic acid was removed under reduced pressure affording 17.1 mg of the title compound as a solid trifluoroacetate. 1H-NMR (DMSO-d6) delta 12.28 (s, 2H), 9.26 (s, 1H), 9.13 (s, 1H), 8.83 (d, 1H, J= 2.8 Hz), 8.26 (d, 1H, J = 8.8 Hz), 7.55 (d, 1H, J = 4.8 Hz), 7.27 (d, 2H, J = 7.6 Hz), 4.42 (d, 1H, J = 15.2 Hz), 4.29 (d, 1H, J = 16.4 Hz), 3.76-3.22 (m, 4H, partially obscured by solvent), 2.91-2.834 (m, 1H), 1.23 (s, 1H); LC-MS: Rt= 0.99 min, m/z 471.4 [M+H]+., 1477-49-2

1477-49-2 3-Indoleglyoxylic Acid 73863, aindole-building-block compound, is more and more widely used in various.

Reference£º
Patent; NOVO NORDISK A/S; Ontogen Corporation; EP1214324; (2006); B1;,
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

52488-36-5,52488-36-5, 4-Bromo-1H-indole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

(a) 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-indole. A 50 mL flask was charged with 4-bromoindole (1.00 g, 5.10 mmol), bis(pinacolato)diboron (1.68 g, 6.63 mmol), KOAc (1.44 g, 15.3 mmol) and PdCl2(dppf) CH2Cl2 complex (206 mg, 0.26 mmol) under argon. Dry DMSO (16 mL) was added and the mixture was heated at 90 C. for 4 h. The reaction mixture was cooled, filtered over silica gel and the filter cake was washed with TBME (2¡Á50 mL). The filtrate was washed with brine (3¡Á50 mL), dried (Na2SO4) and concentrated. The residue was purified by flash chromatography (AcOEt/heptane 1:4) to give 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-indole as an off-white solid (1.24 g, quant.).

As the paragraph descriping shows that 52488-36-5 is playing an increasingly important role.

Reference£º
Patent; Locus Pharmaceuticals, Inc.; US2008/280891; (2008); 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

272-49-1, 4-Azaindole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

2. Synthesis of 3-nitro-l//-pyrrolo[3,2-blpyridine.Nitric acid (286 mmol) is added to a cold (0 0C) solution of lH-pyrrolo[3,2-b]pyridine (254 mmol) in sulfuric acid (120 mL) and the reaction mixture is maintained for 2 h at 0 0C. The reaction mixture is diluted with ice water (300 mL) and the pH is adjusted to 7-8 with 2 M sodium hydroxide. The precipitated solids are collected by filtration and dried to provide 3-nitro-lH- pyrrolo[3,2-b]pyridine in 89percent yield as a yellow solid., 272-49-1

272-49-1 4-Azaindole 9226, aindole-building-block compound, is more and more widely used in various.

Reference£º
Patent; MEMORY PHARMACEUTICALS CORPORATION; DANCA, Mihaela, Diana; DUNN, Robert; TEHIM, Ashok; XIE, Wenge; WO2010/21797; (2010); 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

16382-15-3, Ethyl 5-methylindole-2-carboxylate is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,16382-15-3

A mixture of ethyl 5-methyl-1H-indole-2-carboxylate (2.032 g, 10.00 mmol), 1-iodo-4-methyl-benzene (2.180 g, 10.00 mmol), iodocopper (95.22 mg, 0.5000 mmol), N1,N2-dimethylcyclohexane-1,2-diamine (284.5 mg, 315.4 muL, 2.000 mmol), and potassium phosphate (4.458 g, 21.00 mmol) in toluene (50.00 mL) was heated to reflux for 22 hours. The cooled reaction was filtered and evaporated. The green residue was purified by silica gel chromatography with 0-15percent ethyl acetate in hexanes to give ethyl 5-methyl-1-(p-tolyl)-1H-indole-2-carboxylate (1.43 g, 4.875 mmol, 48.74percent) as a colorless oil. ESI-MS m/z calc. 293.14. found 294.2 (M+1)+. Retention time: 0.83 minutes (1 minute run).

16382-15-3 Ethyl 5-methylindole-2-carboxylate 232919, aindole-building-block compound, is more and more widely used in various.

Reference£º
Patent; VERTEX PHARMACEUTICALS INCORPORATED; Miller, Mark Thomas; Anderson, Corey; Arumugam, Vijayalaksmi; Bear, Brian Richard; Binch, Hayley Marie; Clemens, Jeremy J.; Cleveland, Thomas; Conroy, Erica; Coon, Timothy Richard; Frieman, Bryan A.; Grootenhuis, Peter Diederik Jan; Gross, Raymond Stanley; Hadida-Ruah, Sara Sabina; Haripada, Khatuya; Joshi, Pramod Virupax; Krenitsky, Paul John; Lin, Chun-Chieh; Marelius, Gulin Erdgogan; Melillo, Vito; McCartney, Jason; Nicholls, Georgia McGaughey; Pierre, Fabrice Jean Denis; Silina, Alina; Termin, Andreas P.; Uy, Johnny; Zhou, Jinglan; (590 pag.)US2016/95858; (2016); 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

4837-90-5, 4-Methoxy-1H-indole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 5 1-N-(S)-Glycidyl-4-methoxyindole (2S)-(+)-Glycidyl tosylate (1.55 g, 6.8 mmole) was added to a stirred solution of 4-methoxyindole (1.0 g, 6.8 mmole), sodium hydride (0.3 g, 7.5 mmole) and 18-crown-6 (10 mg) in anhydrous DMF (20 ml), and the mixture was heated at 60C under nitrogen for five hours. Water (100 ml) was added and the product extracted into CH2Cl2 (3 x 25 ml). The combined organics were washed with water (25 ml), brine (25 ml) and dried over anhydrous sodium sulfate. Filtration and concentration in vacuo gave the crude product as a light yellow colored oil (1.15 g). This was purified by flash silica gel chromatography (30% ethyl acetate in hexane) to afford the titled product as a light oil (0.65 g, 47% yield). Elemental Analysis for: C12H13NO2 Calculated: C, 70.92; H, 6.45; N, 6.89 Found: C, 71.11; H, 6.59; N, 6.99 aa–3aa

4837-90-5, The synthetic route of 4837-90-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Wyeth; EP1075471; (2004); B1;,
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