Tag: M.W:200-300

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.923197-75-5,(6-Bromo-1H-indol-2-yl)methanol,as a common compound, the synthetic route is as follows.

923197-75-5, Compound TDI01155-2 (600 mg, 2.65 mmol) was dissolved in acetonitrile (20 mL), MnO2 (692 mg, 7.96 mmol)was added, and the reaction was stirred at room temperature overnight. Thin layer chromatography (petroleum ether :ethyl acetate=5:1) and LC-MS assay indicated the reaction was complete. The reaction solution was concentrated underreduced pressure, and the residue was purified by column chromatography (petroleum ether : ethyl acetate= 10:1 to1:1) to afford compound TDI01155-3 (520 mg, yellow solid, yield: 87.6%).1HNMR (400 MHz, CDCl3) delta 9.86 (s, 1H), 9.22 (s, 1H), 7.65 (s, 1H), 7.61 (d, J = 8.4 Hz, 1H), 7.30-7.28 (m, 1H), 7.25(br, 1H). MS m/z (ESI): 224.0/226.0 [M+H].

As the paragraph descriping shows that 923197-75-5 is playing an increasingly important role.

Reference：
Patent; Beijing Tide Pharmaceutical Co., Ltd.; Zhao, Yanping; Wang, Hongjun; Li, Gong; Jiang, Yuanyuan; Li, Xiang; Zhou, Liying; Liu, Yanan; (235 pag.)EP3421465; (2019); 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

885519-01-7, 6-Bromo-4-chloro-1H-indole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

under nitrogen gas, 6-bromo-5-chloro-1H-indole (8.40g, 36.4mmol) in THF/H2O (80 ml/20 ml), 2-Nitrophenylboronic acid (6.08g, 36.4mmol), and K2CO3(15.1g, 0.109mol), Pd (PPh3)4(2.11g, 1.82mmol) , were added , in 85 C stirred 4 hours. Furthermore, after cooled to room temperature, was of concentrating the THF. After, ethyl which has organic layer which is then subjected to reverse phase, MgSO4in organic layer to the second interlayer, filters the concentrated within column chromatography for purifying the 4-chloro-6 – (2-nitrophenyl) – 1H-indole (8.44g, yield: 85%) is obtained., 885519-01-7

As the paragraph descriping shows that 885519-01-7 is playing an increasingly important role.

Reference：
Patent; Doosan Corporation; Kim, Dae Hyong; Kim, Hoe Moon; Lee, Yong – Hwan; Pek, Young Mi; Park, Hoo Chol; Lee, Chang Joon; Sin, Jin Yong; (81 pag.)KR101601357; (2016); 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

1065181-58-9, Ethyl 5-bromo-1H-indole-7-carboxylate is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Intermediate 31 :Ethyl 5-bromo-3-(8-thiabicyclo[3.2.1]oct-3-yl)-1H-indole-7-carboxylate.To a solution of 8-thiabicyclo[3.2.1]octan-3-one (1.33 g, 9.32 mmol, 1 eq) in dry dichloromethane (50 mL) was added a spatula tip full of activated 4A molecular sieves (beads). The ketone solution was cooled to 0 0C, and trimethylsilyl triflate (1.7 mL, 9.41 mmol, 1 eq) was added dropwise followed by a solution of ethyl 5-bromo-1 H-indole-7- carboxylate (2.5 g, 9.32 mmol, 1 eq) in dichloromethane (25 mL). The mixture was stirred at 23 0C overnight, then was cooled to 23 0C and triethylsilane (2.3 mL, 14.4 mmol, 1.5 eq) was added in a single portion. The reaction was stirred at 23 0C for 1.5h, then quenched by the addition of saturated aqueous sodium bicarbonate. The mixture was extracted with dichloromethane, and the combined organic extracts were dried over sodium sulfate, filtered, and concentrated. The crude product was purified by lsco Combiflash, 120 gram column, eluting with 0-30% ethyl acetate in hexanes. The ethyl 5-bromo-3-(8- thiabicyclo[3.2.1]oct-3-yl)-1 /-/-indole-7-carboxylate was obtained as a mixture of isomers (2.38 g, 65%)., 1065181-58-9

As the paragraph descriping shows that 1065181-58-9 is playing an increasingly important role.

Reference：
Patent; SMITHKLINE BEECHAM CORPORATION; WO2008/118724; (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.434958-85-7,N-Boc-5-Hydroxyindole,as a common compound, the synthetic route is as follows.

PREPARATION 2 5-[(2,3,4-tri-O-acetyl-5-thio-D-xylopyranosyl)oxy]-1H-indole-1-carboxylic Acid 1,1-dimethylethyl Ester A solution of 1.75 g (7.51 mM) of 5-hydroxy-1H-indole-1-carboxylic acid tert-butyl ester in 25 ml of THF, 2.73 g (13.5 mM) of diisopropylazodicarboxylate and 3.54 g (13.5 mM) of triphenylphosphine are added to a solution of 2.85 g (9.75 mM) of 2,3,4-tri-O-acetyl-5-thio-D-xylopyranose in 50 ml of THF. The reaction mixture is stirred at 45 C. for 3 hours and then concentrated under reduced pressure. The evaporation residue is dissolved in ethyl acetate and the organic phase is washed with a 1N solution of sodium hydroxide, and then with a concentrated aqueous solution of ammonium chloride. The organic phase is subsequently dried over magnesium sulfate and concentrated under reduced pressure. The evaporation residue is purified by C18-grafted silica chromatography, elution being carried out with an acetonitrile/water mixture (7/3; v/v). The desired product is obtained in the form of a pale yellow solid with a yield of 11%. Mp=58-62 C.

434958-85-7, 434958-85-7 N-Boc-5-Hydroxyindole 22596220, aindole-building-block compound, is more and more widely used in various fields.

Reference：
Patent; LABORATOIRES FOURNIER S.A.; US2009/118325; (2009); 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

20289-27-4, 7-(Benzyloxy)-1H-indole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

EXAMPLE 93 Preparation of 7-Benzyloxy-3-{4-[(1H-2-methylimidazo[4,5-c]pyrid-1-yl)methyl]benzoyl}indole The desired compound was prepared according to the method of Example 90, except substituting 7-benzyloxyindole for 4,7-dimethoxycarbonylindole. 1 H NMR (DMSO-d6, 300 MHz) delta2.59 (s, 3H), 5.30 (s, 2H), 5.63 (s, 2H), 6.93 (d, 1H, J=7.7 Hz), 7.13 (t, 1H, J=7.9 Hz), 7.28 (d, 2H, J=8.1 Hz), 7.32-7.46 (c, 3H), 7.54-7.60 (c, 2H), 7.62 (d, 1H, J=5.1 Hz), 7.71 (d, 1H, J=2.2 Hz), 7.76 (d, 2H), J=8.5 Hz), 7.80 (d, 1H, J=8.1 Hz), 8.30 (d, 1H, J=5.2 Hz), 8.87 (s, 1H), 12.24 (d, 1H, J=2.6 Hz). MS (DCI/NH3) m/e 473 (M+H)+. IR, cm-1 (microscope) 738 (m), 1219 (m), 1248 (m), 1278 (m), 1436 (s). Anal calcd for C30 H24 N4 O2.1.2 H2 O: C, 72.92; H, 5.38; N, 11.34. Found: C, 72.97; H, 5.30; N, 11.05., 20289-27-4

20289-27-4 7-(Benzyloxy)-1H-indole 260798, aindole-building-block compound, is more and more widely used in various fields.

Reference：
Patent; Abbott Laboratories; US5486525; (1996); 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

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.938465-52-2,1-Chloro-5H-pyrido[4,3-b]indole-4-carboxamide,as a common compound, the synthetic route is as follows.

To a solution of 4-(4-fluorophenyl)- 1 -oxa-4, 8-diazaspiro[5. Sjundecan-5-one (120 mg, 0.45 mmol) in NMP (3 mL) was added 1-chloro-5H-pyrido[4,3-bjindole-4-carboxamide (123 mg, 0.Smmol) and DIEA (174 mg, 1.35 mmol), and the mixture was heated under microwave irradiation for 1.5 h at 150 C.The mixture was purified with prep-HPLC to give 1-(4-(4-fluorophenyl)-5 -oxo- 1 -oxa-4, 8-diazaspiro[5.5j undecan-8-yl)-5H-pyrido [4,3-bj indole-4- carboxamide. ?H NMR (400 MHz, CD3OD) 3 8.51 (s, 1H), 8.03 (d, J=8.0 Hz, 1H), 7.82 (d, J=8.0 Hz, 1H), 7.62 (t, J=7.7 Hz, 1H), 7.54 – 7.44 (m, 1H), 7.31 – 7.23 (m, 2H), 7.14 – 7.06 (m, 2H), 4.40 (d, J=13.3 Hz, 1H), 4.27 – 4.14 (m, 2H), 4.00 – 3.90 (m, 1H), 3.80 – 3.66 (m, 3H), 3.64- 3.52 (m, 1H), 2.54 – 2.39 (m, 1H), 2.38 – 2.22 (m, 2H), 1.94 – 1.79 (m, 1H) ppm., 938465-52-2

As the paragraph descriping shows that 938465-52-2 is playing an increasingly important role.

Reference：
Patent; MERCK SHARP & DOHME CORP.; LIU, Jian; KOZLOWSKI, Joseph; KIM, Ronald; GAO, Xiaolei; BOGA, Sobhana Babu; YU, Younong; WU, Hao; LIU, Shilan; YANG, Chundao; (102 pag.)WO2016/164284; (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

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1167055-46-0,4-Bromo-1H-indole-7-carbonitrile,as a common compound, the synthetic route is as follows.

A mixture of 4-bromo-1/-/-indole-7-carbonitrile (1.0 g), Et3N (7.6 mL), and DMAP (55 mg) in DCM (10 mL) was stirred at 0 0C, 4-methylbenzenesulfonyl chloride (2.59 g) was added in one port. After addition completed, the mixture was stirred at 25 0C overnight. Aqueous NaHCO3 solution (20 mL) and DCM (20 mL) were added; the DCM fraction was separated and dried over anhydrous magnesium sulphate. The dried solution was concentrated in vacuum and the resulting residue was purified by Teledyne ISCO (15% EtOAc in Petroleum) to afford 4-bromo-1-[(4- methylphenyl)sulfonyl]-1 H-indole-7-carbonitrile (D3) (1.05 g) as a grey solid. MS (ES): Ci6HnBrN2O2S requires 374.1 (79Br), 376.0 (81Br); found 375.0 (M+H+, 79Br), 377.1 (IVH-H+, 81Br).

1167055-46-0, 1167055-46-0 4-Bromo-1H-indole-7-carbonitrile 53399521, aindole-building-block compound, is more and more widely used in various fields.

Reference：
Patent; GLAXO GROUP LIMITED; LIN, Xichen; REN, Feng; SI, Yugui; WO2010/145203; (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

923197-75-5, (6-Bromo-1H-indol-2-yl)methanol is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,923197-75-5

(6-Bromo-1H-indol-2-yl)methanol (80 mg, 0.35 mmol) and dess-martin periodinane (178 mg, 0.42 mmol) were dissolved in dichloromethane (10 mL), and it was stirred for 30 minutes at room temperature. The reaction mixture was diluted with ethyl acetate, and it was washed with 10% sodium thiosulfate, saturated NaHC03and brine. The organic layer was dried over Na2S04, and it was concentrated under reduced pressure. The residue was purified on an ISCO chromatograph (0-10% ethyl acetate/hexane) to give product as a white solid (78 mg, 100%);1H NMR (300 MHz) (CDCb) d 9.86 (s, 1H), 9.23 (bs, 1H), 7.65 (s, 1H), 7.61 (d, J= 9 Hz, 1H), 7.29 (d, j= 9 Hz, 1H), 7.26-7.25 (m, 1H).

923197-75-5 (6-Bromo-1H-indol-2-yl)methanol 13567957, aindole-building-block compound, is more and more widely used in various fields.

Reference：
Patent; RUTGERS, THE STATE UNIVERSITY OF NEW JERSEY; TAXIS PHARMACEUTICALS, INC.; LAVOIE, Edmond, J.; SAGONG, Hye Yeon; PARHI, Ajit, K.; (144 pag.)WO2019/99402; (2019); 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.289483-82-5,4-Methyl-7-nitro-1H-indole-3-carbonitrile,as a common compound, the synthetic route is as follows.

Production Example 12 7-Amino-3-cyano-4-methyl-1H-indole 12.6 g (62.6 mmol) of the compound of Production Example 6 was dissolved in a mixed solution of 100 ml of tetrahydrofuran and 100 ml of methanol, and the mixture was hydrogenated at an ordinary temperature under 3 atoms in the presence of 430 mg (1.87 mmol) of platinum oxide. The catalyst was filtered off and the filtrate was concentrated to dryness. Then, a mixed solution of tert-butyl methyl ether and hexane was added to the residue and the crystals were collected by filtration, to give 10.7 g of the title compound. 50.5 g (186 mmol) of the compound of Production Example 11 was dissolved in 400 ml of dichloromethane. In nitrogen atmosphere, 210 ml (2.76 mol) of trifluoroacetic acid was added thereto at 0C, followed by stirring at room temperature for 40 minutes. The reaction mixture was adjusted to pH 7 by adding a 5N aqueous sodium hydroxide thereto. The solvent was removed, and then the residue was extracted with ethyl acetate. The organic layer was successively washed with water and brine, dried over magnesium sulfate and concentrated to dryness. A mixed solution of diethyl ether and hexane was added to the residueand the crystals were collected by filtration, to give 24.5 g of the title compound. 1H-NMR(DMSO-d6) delta (ppm): 2.47(3H, s), 5.07 (2H, s), 6.34(1H, d, J=7.6Hz), 6.64(1H, d, J=7.6Hz), 8.10(1H, s), 11.70(1H, br s)

289483-82-5, 289483-82-5 4-Methyl-7-nitro-1H-indole-3-carbonitrile 11622527, aindole-building-block compound, is more and more widely used in various fields.

Reference：
Patent; Eisai Co., Ltd.; EP1258252; (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

938465-52-2, 1-Chloro-5H-pyrido[4,3-b]indole-4-carboxamide is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,938465-52-2

A mixture of 4-((benzyloxy)methyl)-2-methyl-2,7-diazaspiro[4. s1 decan- 1-one(118 mg, 0.407 mmol), 1-chloro-5H-pyrido[4,3-bjindole-4-carboxamide (100 mg, 0.407 mmol)and DIPEA (0.3 mL, 1.63 mmol) in 1-methylpyrrolidin-2-one (3 mL) was stirred in a microwave at 150 C for 2 h. To the mixture was added water (10 mL). The mixture was extracted withDCM/i-PrOH (3:1, 20 mL )< 3). The combined organic layers were washed with brine (10 mL), dried over sodium sulfate, filtered and concentrated to afford the crude product, which waspurified by silica gel column chromatography (THF / PE = 30% 80 %) to give 1-(4-((benzyloxy)methyl)-2-methyl- 1 -oxo-2,7-diazaspiro [4.51 decan-7-yl)-5H-pyrido [4,3-bj indole-4-+carboxamide as a solid. MS: 498.2[M+Hj As the paragraph descriping shows that 938465-52-2 is playing an increasingly important role. Reference：
Patent; MERCK SHARP & DOHME CORP.; LIU, Jian; KOZLOWSKI, Joseph; KIM, Ronald; GAO, Xiaolei; BOGA, Sobhana Babu; YU, Younong; WU, Hao; LIU, Shilan; YANG, Chundao; (102 pag.)WO2016/164284; (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