Month: March 2022

5192-03-0, 1H-Indol-5-amine is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

DMSO (10 L, 11 kg), 2-amino-3,5-dibromopyrazine (1) (4.5 kg, 17.8 mol, 1 eq.), 5- amino indole (2) (3.06 kg, 23.15 mol, 1.3 eq.) and triethylamine (7.4 L, 5.4 kg, 53.36 mol, 3 eq.) were charged to a reactor. The reaction mixture was heated to 95C while agitated. After 12 hours, the heating was discontinued and the conversion was 88% of 2-amino-3,5-dibromopyrazine. The reaction was heated again to 95C and agitated for an additional 2.5 hours. There was no improvement in conversion. The reaction mixture was agitated at ambient temperature overnight. Triethylamine (3.5 kg) was removed under vacuum and the remaining reaction mixture was transferred to a stainless steel container from which it was charged into another reactor. Subsequently, 8.4 kg of 50% acetic acid (aq.) was introduced over a period of 20 minutes under agitation, followed by purified water (61 L) charged over a period time of 60 minutes. The slurry was then filtered and the isolated material was washed with 2 x 20 L of 1 % acetic acid (aq.). The isolated 3-bromo-N-3-(1H-indol-5-yl)-pyrazine-2,3-diamine) (3) was transferred to a drying cabinet and dried to invariable weight at 40±3C, (19 hours), to afford 4.36 kg, 14.34 mol, 81 % yield, with a purity of 96% by HPLC. The reaction temperature in the batch record was set to be 130-135C. However, at 95C the reaction mixture was at reflux., 5192-03-0

As the paragraph descriping shows that 5192-03-0 is playing an increasingly important role.

Reference：
Patent; AKINION PHARMACEUTICALS AB; LEHMANN, Fredrik; BREMBERG, Ulf; SOeLVER, Ellen; ERIKSSON BAJTNER, Johan; THORNQVIST OLTNER, Viveca; WO2013/89636; (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

399-51-9, 6-Fluoro-1H-indole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Trifluoroacetic anhydride (9.009 ml, 64.8 mmol, 2.2 equiv.) was added drop wise to a stirring solution of 6-fluoroindole (4.000 g, 29.6 mmol, 1.0 equiv.) in DMF (25 mL) at 0C (external ice bath temperature). After 3 hours in the ice bath the mixture was quenched with 40 mL of 2N sodium carbonate. The precipitate was collected by filtration and washed with water. The solid was taken up in 4M NaOH (50 mL) and refluxed for 4 hours. The reaction mixture was cooled to room temperature and poured into 50 mL of water. The mixture was cooled in an ice bath and slowly brought to pH 3 with 6N HCl. The precipitate which formed was collected by filtration, washed with water and dried under vacuum to give an off -white solid (3.5 g, 66%). 1H NMR (DMSO-d6, 300 MHz): 12.03 (bs, 1H), 11.87 (s, 1H), 7.99-7.92(m, 2H), 7.23 (dd, J=9.9 & 2.4 Hz, 1Eta),7.03-6.97 (m, 1H)., 399-51-9

The synthetic route of 399-51-9 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; BUCK INSTITUTE FOR RESEARCH ON AGING; JOHN, Varghese; BREDESEN, Dale, E.; SPILMAN, Patricia, R.; JAGODZINSKA, Barbara; (85 pag.)WO2017/197177; (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.2795-41-7,6-Fluoroindole-3-carboxaldehyde,as a common compound, the synthetic route is as follows.

General procedure: The van Leusen reaction was conducted as describedpreviously [37]. Aromatic aldehyde (3 mmol) was mixed withamine (15 mmol) in 20 mL of dry methanol. The reaction mixturewas left overnight to complete imine formation, although thisprocess can be monitored by this layer chromatography (TLC) (SiO2/CHCl3). Anhydrous K2CO3 (3 mmol) and TosMIC (tosylmethylisocyanide,3 mmol) were subsequently added. The mixture was stirredfor an additional 8 h, diluted with 50 mL of H2O, and extractedthree times with 20 mL of ethyl acetate. The combined extractswere washed twice with 20 mL of H2O, and once with 20 mL ofbrine, treated with anhydrous magnesium sulfate and evaporated.The final products were purified either by trituration under a 2:1hexane:isopropanol mixture, or chromatography on a short silicagelbed. The unreacted aldehydes were eluted with ethyl acetate orchloroform, and a mixture of AcOEt:MeOH or CHCl3:MeOH wasthen applied to elute the product.

2795-41-7, As the paragraph descriping shows that 2795-41-7 is playing an increasingly important role.

Reference：
Article; Hogendorf, Adam S.; Hogendorf, Agata; Popio?ek-Barczyk, Katarzyna; Ciechanowska, Agata; Mika, Joanna; Sata?a, Grzegorz; Walczak, Maria; Latacz, Gniewomir; Handzlik, Jadwiga; Kie?-Kononowicz, Katarzyna; Ponimaskin, Evgeni; Schade, Sophie; Zeug, Andre; Bijata, Monika; Kubicki, Maciej; Kurczab, Rafa?; Lenda, Tomasz; Staro?, Jakub; Bugno, Ryszard; Duszy?ska, Beata; Pilarski, Bogus?aw; Bojarski, Andrzej J.; European Journal of Medicinal Chemistry; vol. 170; (2019); p. 261 – 275;,
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.90924-06-4,1-Methyl-4-indolecarboxylic Acid,as a common compound, the synthetic route is as follows.

90924-06-4, To a stirred SOLUTION OF 4- [ (Z)- (4-BROMOPHENYL) (ethoxyimino) methyl]-1- (4-methyl-4- piperidinyl) piperidine (50 mg, 0.12 MMOL), 1-METHYL-1 H-indole-4-carboxylic acid (23 mg, 0.13 MMOL), and Et3N (24.3 mg, 0.24 MMOL) in DMF (2 mL), HATU (60.8 mg, 0.16 MMOL) was added at room temperature. After 16 h the mixture was poured into ice water (10 mL), and extracted with CH2CI2 (3X10 mL). The organic phase was dried over NA2SO4, and concentrated in vacuo. Purification by preparative TLC afforded title compound as a light YELLOW OIL. H NMR (CDCl3, 400MHz) 8 0.93 (s, 3H), 1.2 (t, 3H), 1.24-2. 2 (m, 11 H), 2.34-2. 46 (m, 1H), 2.76-2. 9 (m, 1 H), 2.9- 3.1 (m, 1H), 3.1-3. 3 (m, 1 H), 3.3-3. 7 (m, 2H), 3.78-3. 84 (s, 3H), 4.02-4. 18 (q, 2H), 6.4-6. 6 (m, 1H), 7.08-7. 14 (m, 4H), 7.19-7. 25 (m, 1H), 7.32-7. 36 (m, 1H), 7.48-7. 56 (m, 2H).

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

Reference：
Patent; SCHERING AKTIENGESELLSCHAFT; WO2004/113323; (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.16732-69-7,Ethyl 7-bromo-1H-indole-2-carboxylate,as a common compound, the synthetic route is as follows.

General procedure: A mixture of lactam(1.0 eq),bromide(2.0 eq),Cul(0.5 eq),(trans)-1,2-N,Ndimethylaminocyclohexane(1.0 eq),and K2C03(2.5 eq) in toluene(1 mL) was sparged withArgas for 5 min. The reaction mixture was sealed and heated to 110 C for 18 h. Same workup and purification protocols described in general coupling procedure A were followed toobtaine a desire product., 16732-69-7

16732-69-7 Ethyl 7-bromo-1H-indole-2-carboxylate 7017885, aindole-building-block compound, is more and more widely used in various fields.

Reference：
Patent; VANDERBILT UNIVERSITY; LEE, Taekyu; TARR, James, C.; JEON, Kyuok; SALOVICH, James, M.; SHAW, Subrata; VEERASAMY, Nagarathanam; KIM, Kwangho; CHRISTOV, Plamen, P.; OLEJNICZAK, Edward, T.; ZHAO, Bin; FESIK, Stephen, W.; BIAN, Zhiguo; (526 pag.)WO2017/152076; (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.434958-85-7,N-Boc-5-Hydroxyindole,as a common compound, the synthetic route is as follows.,434958-85-7

General procedure: A suspension of bismacycle tosylate 1-OTs (1.0 equiv.; initial concentration = 0.05 M),K2CO3 (1.2 equiv.) and arylboronic acid (1.1 equiv.) in toluene/water (99:1,v/v) was stirred at 60 C for 2 h. After cooling to room temperature, substrates(naphthols, 0.90 equiv.; phenols, 3.0 equiv.) and mCPBA (titrated; 1.5 equiv.) were added. The reaction was stirred for 10 min at room temperature and then methanol (2 ml) was added. The mixture was diluted with diethyl ether and washed witha saturated aqueous solution of KHCO3. The organic phase was separated, dried (MgSO4), filtered and concentrated in vacuo before purification by flash column chromatography on silica gel. Following isolation of the desired arylation product, bismacycle acetate 1-OAc can be recovered by flushing the column with diethyl ether to remove organic impurities before elution with 2% acetic acid in methanol.

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

Reference：
Article; Ball, Liam T.; Jurrat, Mark; Lewis, William; Maggi, Lorenzo; Nature Chemistry; vol. 12; 3; (2020); p. 260 – 269;,
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.,31241-19-7

General procedure: 2,3,3-Trimethylindolenine (1 g, 12.56 mmol), acetonitrile (50 mL),and methyl idodide (0.94 mL, 15.072 mmol) were refluxed at 80 C for 7 h. The resulting pink precipitate was filtered and washed with ice-cooled chloroform. Yield: 37%.

As the paragraph descriping shows that 31241-19-7 is playing an increasingly important role.

Reference：
Article; Kim, Bo Hyung; Park, Se Woong; Lee, Donghyun; Kwon, I. I. Keun; Kim, Jae Pil; Bulletin of the Korean Chemical Society; vol. 35; 8; (2014); p. 2453 – 2459;,
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.676273-39-5,3-Iodo-1-tosyl-1H-indole-5-carbonitrile,as a common compound, the synthetic route is as follows.

676273-39-5, Preparation of compound 69c: N’-hydroxy-3-iodo-l-tosyl-l/7-indole-5- carboximidamideTo a suspension of 3-iodo-l-tosyl-l//-indole-5-carbonitrile (1 g, 2.37 mmol) in EtOH (10 mL) was added Et3N (1.65 mL, 11.87 mmol) followed by NH2OH.HCl (410 mg, 5.93 mmol) and the reaction was stirred for 48 h at RT. The solvent was removed in vacuo and the residue was treated with H20 (10 mL) and extracted with EtOAc (25 mL). The aqueous layer was extracted with EtOAc (25 mL). The combined organic layers were dried over anhydrous Na2S04, filtered and concentrated. The residue was further triturated with n-pentane to give N’-hydroxy-3-iodo-l-tosyl-l//-indole-5- carboximidamide (950 mg, 88.7%o) as an off brown solid. MS (ESI, pos. ion) m/z: 455.8; .H NMR (400MHz, CDC13): delta 7.99 (d, J=8.8Hz, 1H), 7.84-7.73 (m, 4H), 7.68 (d, J=8.4Hz, 1H), 7.63-7.61 (m, 1H), 7.31-7.24 (m, 1H), 4.92 (brs, 2H), 3.14-3.09 (m, 1H), 2.36 (s, 3H).

The synthetic route of 676273-39-5 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; AMGEN INC.; WANG, Hui-Ling; CEE, Victor, C.; HERBERICH, Bradley, J.; JACKSON, Claire, L., M.; LANMAN, Brian, Alan; NIXEY, Thomas; PETTUS, Liping, H.; REED, Anthony, B.; WU, Bin; WURZ, Ryan; TASKER, Andrew; WO2012/129338; (2012); 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.399-67-7,7-Fluoro-1H-indole-2-carboxylic acid,as a common compound, the synthetic route is as follows.,399-67-7

To a solution of 7-fluoro-1H-indole-2-carboxylic acid (78 mg, 0.435 mmol), (S)-2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)-5 -(piperidin-3-yl)benzofuran-3 -carboxamide (100 mg, 0.218 mmol) in DCM (1 ml) was added N,N-diisopropylethylamine (169 mg, 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)benzofiiran-3-carboxamide as white solid. LC-MS (ES, mlz) C32H30F2N4055: 620; Found: 621 [M+H]b.

399-67-7 7-Fluoro-1H-indole-2-carboxylic acid 3159626, aindole-building-block compound, is more and more widely used in various fields.

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; WO2014/205592; (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

14618-45-2, 3-(Trifluoroacetyl)indole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

14618-45-2, To a solution of this compound (11 g, 50 mmol) in 100 mL acetone were added MeI (10 mL, 150 mmol) and potassium carbonate (18 g), and stirring was continued at RT for 2 h. Acetone was removed in vacuo. Water and methylene chloride were added to the residue. The organic layer was separated, washed with brine, dried and concentrated in vacuo to yield crude 1-methyl-3-trifluoroacetyl-1H-indole.

The synthetic route of 14618-45-2 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; Monsanto Company; US5994270; (1999); 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