Month: March 2022

289483-82-5, 4-Methyl-7-nitro-1H-indole-3-carbonitrile is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

After suspending 400 g (1.99 mol) of the 3-cyano-4-methyl-7-nitro-1H-indole obtained in Example 1A in a mixture of 6 L of ethyl acetate and 6 L of methanol, the suspension was subjected to hydrogenation in the presence of 40 g of 10% palladium-carbon at ordinary temperature, 4 atmospheres. After removing the catalyst by filtration, the filtrate was treated with activated carbon and concentrated to give crude crystals. The crude crystals were dissolved in 6 L of 1,2-dimethoxyethane at an external temperature of 60C, and then 12 L of water was added dropwise. Upon confirming precipitation of crystals, the mixture was stirred for 1.5 hours while cooling in an ice bath and filtered, and the crystals were washed twice with water (1 L). The crystals were air-dried at 50C for 16 hours to give 289 g of the title compound (yield: 84.8%). HPLC analysis confirmed that the obtained compound was identical to the 7-amino-3-cyano-4-methyl-1H-indole described in WO00/50395.(HPLC conditions) Mobile phase: CH3CN/H2O/70% HClO4 = 400/600/1 (v/v/v)Flow rate: 1.0 mL/minDetection: UV (282 nm)Column: YMC-Pack Pro C18 250 x 4.6 mm, 289483-82-5

As the paragraph descriping shows that 289483-82-5 is playing an increasingly important role.

Reference：
Patent; Eisai Co., Ltd.; EP1666463; (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

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 stirred solution of t-butylmethylamine (2.8 mL, 23.5 mmol, 5 eq.), in THF (40 mL) at 0 C under nitrogen was added slowly n-BuLi (9.4 mL, 23.5 mmol, 2.5 M in hexanes, 5 eq.). The solution was stirred at 0 C for 2 h. To the anion was added 3-trifluoroacetylindole (6) (1.0 g, 4.69 mmol, 1 eq.) in THF (40 ml) at 0 C. The reaction mixture was allowed to gradually warm to rt over 18 h then poured onto ice H2O (75 mL) and stirred for 4 h. The aqueous solution was extracted with CH2Cl2 (4 x 75 mL). The organic extracts were combined, washed with brine (2 x 50 mL), dried (Na2SO4), and concentrated in vacuo to give a yellow oil. This was purified by flash chromatography (2:1 hexanes: EtOAc) to give 7 as a yellow solid (0.91 g, 84%): 1H-NMR (CDCl3) 9.44 (bs, 1H), 7.65-7.68 (m, 1H), 7.32-7.35 (m, 2H), 7.14-7.21 (m, 2H), 3.03 (s, 3H), 1.57 (s, 9H); 13C-NMR (CDCl3) 169.6, 135.7, 127.8, 125.1, 122.3, 120.7, 120.4, 114.9, 111.8, 56.3, 35.2, 27.9; IR (KBr) 3444, 3167, 2945, 1587, 1536, 1446, 1123, 1011 cm-1; UV (95% EtOH) deltamax 296 nm.; MS m/z 230 (M+), 215, 144, 116, 89, 72 (100%). An analytical sample was obtained via iterative recrystallizations from CH2Cl2/hexanes: mp 220-222 C. Anal. Calcd for C14H18N2O: C, 73.01; H, 7.88; N, 12.16. Found: C, 72.80; H, 7.82; N, 12.08.

14618-45-2 3-(Trifluoroacetyl)indole 589126, aindole-building-block compound, is more and more widely used in various fields.

Reference：
Article; Badenock, Jeanese C.; Fraser, Heidi L.; Gribble, Gordon W.; Arkivoc; vol. 2018; 5; (2018); p. 140 – 149;,
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.400071-95-6,5-Bromo-1-methyl-1H-indole-3-carboxylic acid,as a common compound, the synthetic route is as follows.,400071-95-6

In a dry flask under argon, the carboxylic acid (2m) (100 mg, 0.39 mmol) was dissolved in dry dichloromethane (3 mL) and few drops of dry DMF. The sluggish solution was cooled to 0 C and freshly distilled oxalyl chloride (60 mg, 0.47 mmol) was added dropwise. The mixture was then stirred for 4 hours at room temperature and directly evaporated with toluene under reduced pressure. The desired acid chloride was obtained as a yellow solid and used straightaway.

The synthetic route of 400071-95-6 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; Universite Joseph Fourier; Denis, Jean-Noel; Jolivalt, Claude, Marcelle; Maurin, Max, Maurin, Louis; Jeanty, Matthieu; EP2548864; (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.900514-08-1,5-Chloro-3-iodo-7-azaindole,as a common compound, the synthetic route is as follows.

900514-08-1, To 5-chloro-3-iodo- 1H-pyrrolo[2,3-b]pyridine (2, 16.50 g,59.25 mmol) in 250.0 mE of N,N-dimethylformamide, sodium hydride (3.10 g, 60% in mineral oil, 77.5 mmol) was added. The reaction was stirred at room temperature for 90 minutes, then triisopropysilyl chloride (3, 13.00 mE, 61.36 mmol) was added slowly. The reaction was stirred at room temperature overnight, then poured into water and extractedwith ethyl acetate. The organic layer was dried over sodium sulfate, filtered and the filtrate concentrated under vacuum. The resulting material was purified by silica gel colunm chromatography, eluting with 20-100% ethyl acetate in hexane. Appropriate fractions were combined and concentrated undervacuum to provide the desired compound (4, 10.0 g). 5-fluoro-3-iodo-1 -triisopropylsilanyl-1 H-pyrrolo[2,3-b]pyridine is prepared similarly from 5-fluoro-3-iodo-1H-pyrrolo [2,3-b]pyridine.3-Iodo-5-methoxy-1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridine 5,3-iodo-5-trifluoromethyl-1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridine 6, and 3-iodo-4-methoxy-1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridine 73-Iodo-5-methoxy-1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridine 5,3-iodo-5-trifluoromethyl-1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridine 6, and 3-iodo-4-methoxy-1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridine 7

The synthetic route of 900514-08-1 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; Plexxikon Inc.; Zhang, Jiazhong; Ibrahim, Prabha N.; Bremer, Ryan; Spevak, Wayne; Cho, Hanna; US9096593; (2015); B2;,
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.935269-27-5,3-Oxoisoindoline-4-carboxylic acid,as a common compound, the synthetic route is as follows.

935269-27-5, Compound 16f was coupled with 4-methoxyaniline using a coupling agent such as EDCI in DMF to give 3-oxo-2,3-dihydro-lH-isoindole-4-carboxylic acid (4- methoxy-phenyl)-amide Compound 16g 1H NMR (300 MHz, MeOD) 3.80 (s, 3H), 4.56 (s, 2H), 6.94 (d, J = 9 Hz, 2H), 7.70 (d, J = 9 Hz, 2H), 7.78 (m, 2H), 8.40 (m, IH); MS (ESI) m/z: 283 (MH+).

The synthetic route of 935269-27-5 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; JANSSEN PHARMACEUTICA, N.V.; WO2007/47646; (2007); A2;,
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

434958-85-7, N-Boc-5-Hydroxyindole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,434958-85-7

To a mixture of N-Boc-5-hydroxyindole (5.0 g), 1-piperidinepropanol (4.95 mL), Toluene (100 mL) and THF (25 mL), cyanomethylenetributylphosphorane (7.3 mL) was added and the mixture was stirred first at 85 C. for 3 hours, then at 100 C. for 3 hours, and finally at room temperature overnight. The reaction mixture was concentrated under reduced pressure and the resulting residue was purified by silica gel column chromatography (SNAP Cartridge KP-Sil, 100 g) to give the titled compound (3.97 g). MS (ESI pos.) m/z: 359([M+H]+)

As the paragraph descriping shows that 434958-85-7 is playing an increasingly important role.

Reference：
Patent; TAISHO PHARMACEUTICAL CO., LTD; Yoshinaga, Mitsukane; Ishizaka, Tomoko; Wakasugi, Daisuke; Shirokawa, Shin-ichi; Hattori, Nobutaka; Kashiwa, Shuhei; Kuwada, Takeshi; Shimazaki, Youichi; US2015/45551; (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

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1065181-58-9,Ethyl 5-bromo-1H-indole-7-carboxylate,as a common compound, the synthetic route is as follows.

Intermediate 53:Ethyl 5-bromo-3-(tetrahydro-2H-thiopyran-3-yl)-1H-indole-7-carboxylate.Dihydro-2H-thiopyran-3(4/-/)-one (0.217g, 1.86mmol) was dissolved in dichloromethane (23ml_) in an oven dried flask containing 3 A molecular sieves and stirred under argon at 00C. TMS-OTf (0.414g, 1.86mmol, 0.33 ml.) was added slowly to the mixture over 10 min.Ethyl 5-bromo-1 /-/-indole-7-carboxylate (0.5g, 1.86mmol) was dissolved in DCM (7ml_) and added to the reaction via syringe pump over 2 hours, after which it was stirred for 3 hours between 0 and 10 0C. The reaction was cooled to 0 0C and triethylsilane (0.325g, 0.44ml_, 2.8mmol) was added all at once and the reaction was stirred at room temperature for 18 hours. The reaction was then quenched with a saturated sodium bicarbonate solution and extracted with DCM. The combined organics were washed with water. The combined aqueous layers were back-extracted with DCM. The combined organics were washed with brine, dried with MgSO4, and concentrated. The crude compound was purified on a Combiflash silica column with 5-25% EA/Hexane to give 0.279g (40%) of the title compound.LC/MS: m/z 369 (M+H), Rt 2.74 min., 1065181-58-9

1065181-58-9 Ethyl 5-bromo-1H-indole-7-carboxylate 59332585, aindole-building-block compound, is more and more widely used in various fields.

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

525593-33-3,525593-33-3, 3-Bromo-5-nitroindole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step 1 : 3-Bromo-1-methyl-5-nitro-1 /-/-indole. To a solution 3-bromo-5-nitro-1 H-indole (5.5 g, 20.6 mmol) in THF (50ml_) at 0 C was added NaH (1.9 g, 41.3 mmol, 60% w/w in mineral oil). The mixture was stirred for 15 min and methyl iodide (6.4 ml_, 103.3 mmol) was added. The reaction mixture was warmed to room temperature and stirred for 16 h. After completion, the reaction mixture was cooled, quenched with addition of ice-cooled water and extracted using EtOAc. The combined organic layer was dried over anhydrous Na2S04i filtered and concentrated to obtain a crude product which was purified by triturating with diethyl ether to afford the title compound (5 g, 86%). 1H NMR (400 MHz, CDCI3) delta 8.55 (d, J = 2.4 Hz, 1 H), 8.17 (dd, J = 8.8, 2.0 Hz, 1 H), 7.36 (d, J = 8.8 Hz, 1 H), 7.25 (s, 1 H), 3.87 (s, 3H).

As the paragraph descriping shows that 525593-33-3 is playing an increasingly important role.

Reference：
Patent; PFIZER INC.; SCHNUTE, Mark Edward; FLICK, Andrew Christopher; JONES, Peter; KAILA, Neelu; MENTE, Scot Richard; TRZUPEK, John David; VAZQUEZ, Michael L.; XING, Li; ZHANG, Liying; WENNERSTAL, Goran Mattias; ZAMARATSKI, Edouard; (82 pag.)WO2016/120850; (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.2795-41-7,6-Fluoroindole-3-carboxaldehyde,as a common compound, the synthetic route is as follows.

General procedure: A mixture of glyoxalylhydrazide 18 (1.47mmol) and aldehyde 20 or 22 (1.47mmol) in ethanol (5mL) was refluxed for 6h. After completion of the reaction, ethanol was distilled off and the residue was taken into water (10mL) and allowed to stir at room temperature for 30min. The obtained suspension was filtered, washed with water and dried to obtain yellow solid ketohydrazide-hydrazones 21a-o and 23a-e in 88-96% yields., 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：
Article; Tantak, Mukund P.; Klingler, Linus; Arun; Kumar, Anil; Sadana, Rachna; Kumar, Dalip; European Journal of Medicinal Chemistry; vol. 136; (2017); p. 184 – 194;,
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

525593-33-3,525593-33-3, 3-Bromo-5-nitroindole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step B: A solution of 3-bromo-5-nitroindole from above (625 mg, 2.1 mmol), phenylboronic acid (381 mg, 3.13 mmol), triphenylphosphine (109.3 mg, 0.417 mmol) in dimethoxyethane (4.16 mL) was degassed. To this mixture 2N sodium carbonate (6.25 mL) was added, and reaction mixture was degassed again. To the reaction was added palladium (II) acetate (23.4mg, 0.104 mmol), and the reaction was refluxed under dry nitrogen with stirring for 8 hours. The reaction mixture was then diluted with 1 M HCl (100 mL), and extracted with ethyl acetate (100 mL). The organic phase was washed with water (100 mL), and brine (100 mL). The organic phase was dried over MgSO4 and concentrated in vacuo. The crude product was purified by chromatography over silica gel (EtOAc/hexanes, 10/90) to afford 3-phenyl-5-nitroindole as an orange powder (45 mg, 9% yield).

The synthetic route of 525593-33-3 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; PTC THERAPEUTICS, INC.; HWANG, Peter Seongwoo; TAKASUGI, James; REN, Hongyu; WILDE, Richard Gerald; TURPOFF, Anthony; AREFOLOV, Alexander; KARP, Gary Mitchell; CHEN, Guangming; CAMPBELL, Jeffrey Allen; WO2006/19831; (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