Month: March 2022

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 80:Ethyl 5-Bromo-3-[2-(1 -methylethyl)tetrahydro-2H-thiopyran-4-yl]-1 H-indole-7- carboxylate.2-(1-methylethyl)tetrahydro-2H-thiopyran-4-one (1.185 g, 7.49 mmol) was dissolved in dry dichloromethane (DCM) (20 ml_), cooled in an ice bath to ca 0 0C, and stirred under argon. Trimethylsilyl trifluoromethanesulfonate (2.71 ml_, 14.98 mmol) was added dropwise over 10 minutes, and dry DCM (5 ml.) was used to wash in the last of the trimethylsilyltrifuoromethanesulfonate. To this mixture was added dropwise, a solution of ethyl 5-bromo-1 H-indole-7-carboxylate (2.145 g, 8 mmol) in dry DCM (20 ml_), and then an additional portion of dry DCM (5 ml.) was used to wash the last of ethyl 5-bromo-1 H- indole-7-carboxylate into the reaction. Triethylsilane (4.77 ml_, 30.0 mmol) was added to the reaction in one portion. The resulting mixture was stirred 2h at 0 0C, and left stirring at 23 0C overnight. The reaction was diluted with saturated aqueous sodium bicarbonate, and the resulting biphasic mixture was extracted with DCM, dried (MgSO4) and the DCM was removed in vacuo to give the title compound as a dark yellow oil. LC/MS: m/z 414.3 (M+H), Rt 1.58 min.

1065181-58-9, The synthetic route of 1065181-58-9 has been constantly updated, and we look forward to future research findings.

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.162100-95-0,6-Fluoro-5-methyl-1H-indole,as a common compound, the synthetic route is as follows.,162100-95-0

A solution of 6-fluoro-5-methyl-1 H-indole [CAS 162100-95-0] (1 .7 g, 1 1 .4 mmol) in CH2CI2 (100 mL) was cooled to 0C under N2-atmosphere. A solution of diethylalunninunn chloride 1 M in hexane (17.1 mL, 17.1 mmol) was added dropwise and the resulting mixture was kept at 0C for 15 min. A solution of 2-(4-chloro- 2-methoxyphenyl)acetyl chloride 1a (3.50 g, 16 mmol) in CH2CI2 (50 mL) was added dropwise. Stirring was continued at 0C for 1 h and at room temperature for 2 h. The reaction mixture was poured out in a stirring ice/Rochelle salt solution. After the ice had melted, the mixture was filtered over dicalite and the filter cake was washed several times with THF. The filtrates were combined. The layers were separated and the organic layer was washed with brine, dried over MgSO4, filtered and evaporated under reduced pressure. The solid residue was suspended in CH2CI2 (30 ml_), the precipitate was filtered off and dried under vacuum at 50C to provide 2-(4-chloro-2-methoxyphenyl)-1 -(6-fluoro-5-methyl-1 H-indol-3-yl)ethanone 7a (2.76 g).

As the paragraph descriping shows that 162100-95-0 is playing an increasingly important role.

Reference：
Patent; JANSSEN PHARMACEUTICALS, INC.; KATHOLIEKE UNIVERSITEIT LEUVEN; KESTELEYN, Bart, Rudolf, Romanie; BONFANTI, Jean-Francois; JONCKERS, Tim, Hugo, Maria; RABOISSON, Pierre, Jean-Marie, Bernard; BARDIOT, Dorothee, Alice, Marie-Eve; MARCHAND, Arnaud, Didier, M; (68 pag.)WO2016/180696; (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

1059630-08-8, (4aS,9bR)-Ethyl 6-bromo-3,4,4a,5-tetrahydro-1H-pyrido[4,3-b]indole-2(9bH)-carboxylate is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

1.000 equivalents of ethyl (4aS,9bR)-6-bromo-l,3,4,4a,5,9b-hexahydro-2H- pyrido[4,3-b]indole-2-carboxylate is charged into a reactor with 0.50 volumes of dimethylacetamide solvent at 20 C. A solution of 1.500 equivalents of N-methyl chloroacetamide in 0.30 volumes of dimethylacetamide is added, followed by 1.000 equivalents of potassium iodide, and 1.700 equivalents of diisopropylethylamine. The resulting suspension is heated at 102 C for 15 to 18 hours. After cooling to 45 C, 5.00 volumes of water are added. After further cooling and agitation, the product is isolated as a solid filter cake and is washed with additional water and dried under vacuum., 1059630-08-8

1059630-08-8 (4aS,9bR)-Ethyl 6-bromo-3,4,4a,5-tetrahydro-1H-pyrido[4,3-b]indole-2(9bH)-carboxylate 59317960, aindole-building-block compound, is more and more widely used in various fields.

Reference：
Patent; INTRA-CELLULAR THERAPIES, INC.; LI, Peng; ZHANG, Qiang; (113 pag.)WO2019/241278; (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

1245643-61-1, Methyl 5-chloro-1H-indole-6-carboxylate is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A mixture of methyl 5-chloro-1 /-/-indole-6-carboxylate (500 mg, 2.39 mmol), B0C2O (781 mg, 3.58 mmol) and DMAP (58.3 mg, 0.477 mmol) in MeCN (8 mL) was stirred at room temperature for 16 h then concentrated in vacuo. The crude product was purified by fee (24 g, 0-50% EtOAc in isohexane) to return the title compound (737 mg, quant) as a colourless oil, which solidified on standing. LCMS [M+H]+ 310; 1 H NMR (400MHz, DMSO-d6) delta 8.59 (s, 1 H), 7.91 (d, J = 3.1 Hz, 1 H), 7.86 (s, 1 H), 6.77 (dd, J = 3.7, 0.7 Hz, 1 H), 3.88 (s, 3H), 1.63 (s, 9H).

1245643-61-1, As the paragraph descriping shows that 1245643-61-1 is playing an increasingly important role.

Reference：
Patent; CANCER RESEARCH TECHNOLOGY LIMITED; JORDAN, Allan; NEWTON, Rebecca; (174 pag.)WO2017/178844; (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.61019-05-4,5-Methoxy-7-methyl-1H-indole,as a common compound, the synthetic route is as follows.

61019-05-4, Oxalyl chloride (0.17 mL, 1.93 mmol) was added dropwise via syringe over 1 min to DMF (1.5 mL) in a vial charged with a magnetic stir bar under N2 at 0 C. After ~30 min, 5-methoxy-7-methyl-1H-indole (342 mg, 2.123 mmol) was added dropwise via syringe over ~30 s as a solution in DMF (2 mL). The reaction was allowed to warm to room temperature and stir overnight, after which 1 N NaOH (2 mL) was added dropwise via syringe over 30 s. The reaction was then heated to 100 oC for 20 min, after which it was cooled to room temperature. After 28 h of total reaction time, the mixture was diluted with H2O (15 mL) and DCM (20 mL). The organic layer was separated, and the aqueous layer was washed with DCM (10 mL). The combined organic layers were washed with H2O (2 × 15 mL) and brine (10 mL), dried with Na2SO4, filtered, and concentrated in vacuo to provide a dark red crude residue. The crude material was purified via flash chromatography on silica (24 g column, 0-60% EtOAc/heptane) to afford 300 mg (82% yield) of 13 as a pale yellow solid. 1H NMR (400 MHz, DMSO-d6) delta ppm 12.27 – 11.84 (m, 1H), 9.89 (s, 1H), 8.20 (d, J = 3.30 Hz, 1H), 7.41 (d, J = 2.45 Hz, 1 H), 6.71 (dd, J = 2.32, 0.73 Hz, 1H), 3.76 (s, 3H), 2.48 – 2.43 (m, 3H); LCMS m/z = 190.2 ([M+H]+), tR = 1.00 min (method A).

The synthetic route of 61019-05-4 has been constantly updated, and we look forward to future research findings.

Reference：
Article; DeChristopher, Brian; Park, Soo-Hee; Vong, Linh; Bamford, Derek; Cho, Hyun-Hee; Duvadie, Rohit; Fedolak, Allison; Hogan, Christopher; Honda, Toshiyuki; Pandey, Pramod; Rozhitskaya, Olga; Su, Liansheng; Tomlinson, Elizabeth; Wallace, Iain; Bioorganic and Medicinal Chemistry Letters; vol. 29; 8; (2019); p. 991 – 994;,
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

2795-41-7, 6-Fluoroindole-3-carboxaldehyde is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

2 g of intermediate I-1 and 6 g of ethoxycarbonyl methylene triphenylphosphine are dissolved in 50 ml of dry acetonitrile.70 overnight.TLC showed complete conversion of the substrate.Stop the reaction,The reaction was cooled to room temperature.Add 50ml ethyl acetate and 50ml water,Extraction and separation of water layer,The organic layer is dry,concentrate,Column chromatography gave 6.1 g of intermediate I-17 (white solid, yield 85%).

2795-41-7, 2795-41-7 6-Fluoroindole-3-carboxaldehyde 262903, aindole-building-block compound, is more and more widely used in various fields.

Reference：
Patent; Chinese Academy Of Sciences Shanghai Pharmaceutical Institute; Hu Youhong; Geng Meiyu; Xing Weiqiang; Ding Jian; Ai Jing; (86 pag.)CN103664895; (2018); B;,
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.39689-58-2,2-(1H-Indol-6-yl)acetic acid,as a common compound, the synthetic route is as follows.

Hydroxybenzotriazole (614 mg, 4.5 mmol), 4-ethylmorpholine (320 mul, 2.5 mmol), propargylamine (160 mul, 2.5 mmol) and 1-[3-(dimethylamino)-propyl]-3-ethylcarbodiimide hydrochloride (523 mg, 2.7 mmol) were added to an ice cold solution of (1H-indol-6-yl)-acetic acid (640 mg, 2.2 mmol; U.S. Pat. No. 4,894,386 A) in tetrahydrofuran (6.4 ml). The solution was naturally warmed to ambient temperature and stirred for 14 h. Ice water/brine 1/1 was added and the mixture was extracted two times with dichloromethane. The combined extracts were successively washed with 1 N HCl, brine, 1 N NaOH and brine, and dried over sodium sulfate. The solvent was removed under reduced pressure to give brown crystals which were recrystallized from heptane/dichloromethane to give 380 mg (1.8 mmol, 80%) of the title compound as colorless crystals. MS: 213.4 (M+H)+., 39689-58-2

39689-58-2 2-(1H-Indol-6-yl)acetic acid 14882503, aindole-building-block compound, is more and more widely used in various fields.

Reference：
Patent; Ackermann, Jean; Aebi, Johannes; Binggeli, Alfred; Grether, Uwe; Kuhn, Bernd; Maerki, Hans-Peter; Meyer, Markus; US2006/35956; (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.219552-64-4,tert-Butyl 6-nitro-1H-indole-1-carboxylate,as a common compound, the synthetic route is as follows.

Step 2.Synthesis of 6-Amino-2,3-dihdro-indole-1-carboxylic acid t-butyl ester 6-Nitro-indole-1-carboxylic acid t-butyl ester (1 eq) was dissolved in methanol (0.1M), to this solution was added palladium on carbon (0.1 eq) in methanol under nitrogen.A hydrogen atmosphere was then inserted and resulting mixture allowed to stir for 3 hours at room temperature.The reaction mixture was then filtered through celite and solvent removed in vacuo to afford 6-Amino-2,3-dihdro-indole-1-carboxylic acid t-butyl ester as a white solid. MS: MH+235, 219552-64-4

219552-64-4 tert-Butyl 6-nitro-1H-indole-1-carboxylate 22240526, aindole-building-block compound, is more and more widely used in various fields.

Reference：
Patent; Amiri, Payman; Fantl, Wendy; Levine, Barry Haskell; Poon, Daniel J.; Ramurthy, Savithri; Renhowe, Paul A.; Subramanian, Sharadha; Sung, Leonard; US2004/122237; (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

399-67-7, 7-Fluoro-1H-indole-2-carboxylic acid is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of 7-fluoro-1H-indole-2-carboxylic acid (78 mg, 0.435 mmol), (5)- 2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)-5 -(piperidin-3 -yl)benzofuran-3 – carboxamide (100 mg, 0.2 18 mmol) in DCM (1 ml) was added N,N-diisopropylethylamine (169mg, 1.306 mmol), and the reaction mixture stirred for 5 mm at RT. Then 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane 2,4,6-trioxide (415 mg, 0.653 mmol) was added to the reaction mixture and stirred at RT overnight under N2 protection. The reaction mixture was concentrated under vacuum, then applied onto a silica gel column and eluted with 0-30% MeOH/EtOAc. This resulted in 78 mg (58%) of (S)-5-( 1 -(7-fluoro- 1 H-indole-2-carbonyl)piperidin-3 -yl)-2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3 -carboxamide as white solid. LC-MS (ES, mlz) C32H30F2N4055: 620; Found: 621 [M+H].

399-67-7, As the paragraph descriping shows that 399-67-7 is playing an increasingly important role.

Reference：
Patent; MERCK SHARP & DOHME CORP.; HE, Shuwen; LAI, Zhong; DAI, Xing; XIAO, Dong; LONDON, Clare; ZORN, Nicolas; NARGUND, Ravi; PALANI, Anandan; MCCOMAS, Casey, C.; LI, Peng; PENG, Xuanjia; SOLL, Richard; WO2014/209729; (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

90924-06-4, 1-Methyl-4-indolecarboxylic Acid is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,90924-06-4

General procedure: To a stirred solution of 25 (115 mg, 0.5 mmol) in DCM (10 mL) was added carboxylic acid (0.5 mmol), HOBT (68 mg, 0.5 mmol) and EDCI·HCl (144 mg, 0.75 mmol). The mixture was stirred at room temperature overnight, and washed successively with water (5 mL) and brine (10 mL × 2). The organic layer was dried over anhydrous Na2SO4, and concentrated to give the crude product, which was purified by flash chromatography (hexane/EtOAc = 3:1-1:1) afforded 4a-w.

90924-06-4 1-Methyl-4-indolecarboxylic Acid 14987287, aindole-building-block compound, is more and more widely used in various fields.

Reference：
Article; Xia, Guangxin; You, Xiaodi; Liu, Lin; Liu, Haiyan; Wang, Jianfa; Shi, Yufang; Li, Ping; Xiong, Bing; Liu, Xuejun; Shen, Jingkang; European Journal of Medicinal Chemistry; vol. 62; (2013); p. 1 – 10;,
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