Indole Building Blocks

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.6960-42-5,7-Nitro-1H-indole,as a common compound, the synthetic route is as follows.,6960-42-5

Step A. NJV-Dimethyl-l-r7-nitro-lH-indol-3-vnmethanamineA mixture of 7-nitro- IH- indole (3 g, 18.5 mmol), 40% aqueous dimethylamine (3.12 mL, 27.7 mmol) and 37% aqueous formaldehyde (1.57 mL, 19.3 mmol) was stirred for three days at ambient temperature. The reaction mixture was diluted with H2O (20 mL) followed 15% aqueous NaOH (200 mL) and extracted with CHCl3 (3 x 200 mL). The combined organic extracts were dried over Na2SO4, filtered, and concentrated in vacuo to give the title compound in sufficient purity for use in the next step. MS: m/z = 181 (M + 1).

The synthetic route of 6960-42-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; MERCK & CO., INC.; WO2008/153852; (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

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.700-06-1,Indole-3-Carbinol,as a common compound, the synthetic route is as follows.,700-06-1

20 mL of a tubular reactor was charged with 3-indole methanol (73.5 mg, 0.50 mmol), triethyl phosphite(166.0 mg, 1.0 mmol, 2.0 equiv.) And tetrabutylammonium iodide (9.3 mg, 0.025 mmol, 5 mol%),Vacuum nitrogen, and then heated to 120 C for 24 h under solvent-free conditions. After the TLC monitoring reaction was complete, the product was purified by column chromatography and the yield was 83%.

The synthetic route of 700-06-1 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Wenzhou University; Xu Qing; Ma Xiantao; Su Chenliang; Han Libiao; (11 pag.)CN106543221; (2017); A;,
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, 5-Bromo-1H-indole-2-carboxylic acid is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,7254-19-5

Example 20 Preparation of 4S-[(5-bromo-1H-indole-2-carbonyl)-amino]-5-(2-oxo-pyrrolidin-3S-yl)-pent-2-enoic Acid Compound 20 was prepared according to the method of Example 1, using 5-bromo-2-indolecarboxylic acid. 1H NMR (CDCl3) delta9.94 (1H, s), 8.94 (1H, d, J=5.9), 7.73 (1H, s), 7.30 (2H, s), 7.07 (1H, d, J=1.8) 6.95 (1H, dd, J=15.6, 5.3), 6.42 (1H, s), 6.03 (1H, dd, J=15.6, 1.4), 4.80-4.65 (1H, m), 4.17 (2H, q, J=7.1), 3.45-3.35 (2H, m), 2.70-2.55 (1H, m), 2.50-2.38 (1H, m), 2.15-1.78 (3H, m), 1.27 (3H, t, J=7.1). MS (FAB) 448.0858 (MH+, calcd 448.0872), 470 (MNa+).

The synthetic route of 7254-19-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Johnson, Jr., Theodore O.; Chu, Shao Song; Eastman, Brian Walter; Hua, Ye; Luu, Hiep The; Reich, Siegfried Heinz; Skalitzky, Donald James; Yang, Yi; Hendrickson, Thomas F.; Chan, Fora P.; US2002/61916; (2002); 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

81868-12-4, 2-(5-Bromo-1H-indol-3-yl)ethanamine hydrochloride is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,81868-12-4

A solution of 4-((3-fluorophenyl)(methyl)amino)benzoic acid (0.250 g, 1.09 mmol), 2-(5-bromo-1H-indol-3-yl)ethanamine hydrochloride (0.300 g; 1.09 mmol), HATU (0.414 g; 1.09 mmol) and N,N-diisopropylethylamine (0.469 mL; 2.72 mmol) in DMF (7 mL), was stirred at room temperature for 72 hours. The reaction mixture was then partitioned between ethyl acetate and sodium hydrogen sulfate and the organic layer was successively washed with a saturated aqueous solution of sodium carbonate and brine. The organic layer was dried, concentrated under reduced pressure and the crude material was purified by flash chromatography on silica gel (eluent 1 to 20% ethyl acetate in dichloromethane) to afford 0.395 g (81%) of the title compound as a white solid. [0652] ESI/APCI(+): 451, 453 (M+H); 473,475 (M+Na); ESI/APCI(-): 450, 451 (M-H).

The synthetic route of 81868-12-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Griffioen, Gerard; Van Dooren, Tom; Rojas De La Parra, Veronica; Allasia, Sara; Marchand, Arnaud; Kilonda, Amuri; Chaltin, Patrick; US2013/274260; (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

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.883500-73-0,5-Bromo-7-fluoro-1H-indole,as a common compound, the synthetic route is as follows.,883500-73-0

A mixture of reagent 1 (30 g, 140.8 mmol), Zn(CN)2 (9.8 g, 84.5 mmol), Zn (2.3 g, 35.2 mmol), Pd2(dba)3 (6.45 g, 7.04 mmol), dppf (7.80 g, 14.1 mmol) in DMA (200 mL) was refluxed for 12 hours under N2. The mixture was cooled to room temperature, filtered and the filtrate was concentrated in vacuo. The residue was extracted with EtOAc (300 mL). The combined organic layers were washed with brine (100 mL), dried over Na2S04 and evaporated to dryness. Flash chromatography (silica, petroleum ether: EtOAc 40:1 to 2:1 ) gave reagent 2 as a yellow solid (15.4 g, 68%). 1H NMR (CDCI3) delta 8.71 (s, 1 H), 7.81 (s, 1 H), 7.38 (m, 1 H), 7.15 (m, 1 H), 6.68-6.70 (m, 1 H).

The synthetic route of 883500-73-0 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; H. LUNDBECK A/S; ESKILDSEN, J¡ãrgen; WO2014/49133; (2014); 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

883535-89-5, 2-(2-Methyl-1H-indol-1-yl)ethanamine is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,883535-89-5

N-(2-(2-Methyl-lH-indol-l-yl)ethyl)-4-(piperidin-l-yl)benzamide (7k) (TG7-152) (Typical procedure): A solution of 2-(2-methyl-lH-indol-l-yl)ethanamine (4a) (65 mg, 0.373 mmol) and 4-(piperidin-l-yl)benzoic acid (5) (76 mg, 1 eq.), and dimethylaminopyridine (catalytic, ~5 mg) in dichloromethane (6 mL) was added l-ethyl-3-(3-dimethylaminopropyl)- carbodiimide.hydrochloride (EDCI) (92 mg, 1.3 eq.) at room temperature. The resulting reaction mixture was stirred for 6 h. At the conclusion of the reaction (TLC), water (15 mL) was added to quench the reaction. The product was extracted with ethyl acetate (20 mL x 3). Organics were washed with dilute HC1 (10 mL), saturated NaHC03 solution (10 ml), water (10 ml) and brine solution (10 ml) and dried over Na2S04 and concentrated. The resulting crude product was subjected to silica gel chromatography eluting with 0-40% ethyl acetate in hexane to furnish 7k (TG7-152) (100 mg, 74% yield). 1H NMR (CDC13): delta 7.52 (d, J = 5.6 Hz, 1H), 7.49 (d, J = 8.8 Hz, 2H), 7.30 (d, J = 8 Hz, 1H), 7.07 (m, 2H), 6.80 (m, 2H), 6.23 (s, 1H), 5.98 (t, J = 5.4 Hz, 1H), 4.33 (t, J = 6 Hz, 2H), 3.76 (q, J = 6 Hz, 2H), 3.25 (t, J = 4.8 Hz, 4H), 2.37 (s, 3H), 1.6 (m, 6H). LCMS (ESI): > 97% purity at lambda 254, MS; m/z, 362 [M+H]+. Anal. Calcd. for C23H27N30: C, 76.42; H, 7.53; N, 11.62; found; C, 75.55; H, 7.50; N, 11.26.

The synthetic route of 883535-89-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; EMORY UNIVERSITY; GANESH, Thota; JIANG, Jianxiong; DINGLEDINE, Ray J.; WO2015/167825; (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

883535-89-5, 2-(2-Methyl-1H-indol-1-yl)ethanamine is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,883535-89-5

General procedure: A solution of 2-(2-methyl-1H-indol-1-yl)ethanamine (4a) (65 mg, 0.373 mmol) and 4-(piperidin-1-yl)benzoic acid (5) (76 mg, 1 eq.), and dimethylaminopyridine (catalytic, ?5 mg) in dichloromethane (6 mL) was added 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide.hydrochloride (EDCI) (92 mg, 1.3 eq.) at room temperature. The resulting reaction mixture was stirred for 6h. At the conclusion of the reaction (TLC), water (15 mL) was added to quench the reaction. The product was extracted with ethyl acetate (20mL¡Á3). Organics were washed with dilute HCl (10 mL), saturated NaHCO3 solution (10 mL), water (10 mL) and brine solution (10 mL) and dried over Na2SO4 and concentrated. The resulting crude product was subjected to silica gel chromatography eluting with 0-40% ethyl acetate in hexane to furnish 7k (TG7-152) (100mg, 74% yield). 1H NMR (CDCl3): delta 7.52 (d, J=5.6Hz, 1H), 7.49 (d, J=8.8Hz, 2H), 7.30 (d, J=8Hz, 1H), 7.07 (m, 2H), 6.80 (d, J=8.2Hz, 2H), 6.23 (s, 1H), 5.98 (t, J=5.4Hz, 1H), 4.33 (t, J=6Hz, 2H), 3.76 (q, J=6Hz, 2H), 3.25 (t, J=4.8Hz, 4H), 2.37 (s, 3H), 1.6 (m, 6H). LCMS (ESI): >97% purity at lambda 254, MS; m/z, 362 [M+H]+. Anal. Calcd. for C23H27N3O: C, 76.42; H, 7.53; N, 11.62; found; C, 76.48; H, 7.55; N, 11.59.

The synthetic route of 883535-89-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Ganesh, Thota; Jiang, Jianxiong; Dingledine, Ray; European Journal of Medicinal Chemistry; vol. 82; (2014); p. 521 – 535;,
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

916179-87-8, 3-Bromoindole-5-carboxylic Acid is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,916179-87-8

To a mixture of 50 (1.0 g, 4.2 mmol) and K2CO3 (0.865 g, 1.5 eq.) inDMF (15 mL) was added CH3I (337 muL, 1.3 eq.) at room temperature (Scheme 9). After stirring for 1.2 hours, the reaction was quenched with a saturated solution of NH4Cl (10 mL). The aqueous layer was extracted with ethyl acetate (3 x 15 mL) and the combined organic layer was dried with MgStheta4, filtered and concentrated under reduced pressure. The residue was purified by flash column chromatography (15% ethyl acetate in hexane) to afford 51 (1.01 g, 95%). 1H NMR (DMSO): 3.87 (s, 3H), 7.53 (d, IH, J=8.6), 7.71 (s, IH), 7.35 (dd, IH, J=8.6, 1.5), 7.64(s, IH), 11.41 (s, IH).

The synthetic route of 916179-87-8 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; QUEEN’S UNIVERSITY AT KINGSTON; WO2006/125324; (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

4769-97-5, 4-Nitroindole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of 4-nitro-indole (1 equiv.) in dimethylformamide was added sodium hydride (1.50 equiv.) and benzenesulfonyl chloride (1.0 equiv.). The mixture was stirred at 0?30 C. for 2 h, and quenched with aqueous ammonium chloride at 0 C. The mixture was filtered, the solids were washed with water and petroleum ether, and the resulting solution was concentrated and dried in vacuo to give 4-nitro-1-(phenylsulfonyl)-1H-indole.

4769-97-5 4-Nitroindole 145766, aindole-building-block compound, is more and more widely used in various.

Reference£º
Patent; PMV Pharmaceuticals, Inc.; Vu, Binh; Dominique, Romyr; Li, Hongju; (222 pag.)US2017/240525; (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

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.16732-70-0,Ethyl 5-bromo-1H-indole-2-carboxylate,as a common compound, the synthetic route is as follows.

Example 88 5-[l-(2-Oxo-pyrrolidin-l-yl)-ethyl]-lH-indole-2-carboxylic acid (3,5-difluoro-phenyl)- amide a) 5-ri-(2-Oxo-pyrrolidin-l-yl)-vinyll-lH-indole-2-carboxylic acid ethyl ester Palladium- (II) -acetat (17 mg) and tri-(o-tolyl)pho spine (68 mg) were dissolved in DMF (10 mL), then 5-bromo-lH-indole-2-carboxylic acid ethyl ester (400 mg), sodium hydrogen carbonate (501 mg), Nu,Nu-diisopropyl ethyl amine (1.02 mL) and l-vinyl-2-pyrrolidon (207 mg) were added. The reaction was stirred at 125C for 1.5 hours, followed by extraction with ethyl acetate and water. Column chromatography on silica gel using heptane / ethyl acetate (1: 1) yielded the title compound as the minor component of the reaction as a light grey solid (161 mg, 36 %). MS ISP (m/e): 299.2 (100) [(M+H)+].

As the paragraph descriping shows that 16732-70-0 is playing an increasingly important role.

Reference£º
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; BAUMANN, Karlheinz; FLOHR, Alexander; JOLIDON, Synese; KNUST, Henner; LUEBBERS, Thomas; NETTEKOVEN, Matthias; WO2014/60386; (2014); 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