Tag: M.W:200-300

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

Furthermore, 7-benzyloxyindole (404 mg, 1.81 mmol) was hydrogenated over 10% palladium on carbon (40 mg) in EtOH (4.2 mL) at ambient temperature under atmosphere pressure for 6 h. The catalyst was filtered off and washed with EtOH. The filtrate was concentrated to give 7-hydroxyindole as pale purple crystals, which was rapidly and directly used for the next reaction., 20289-27-4

The synthetic route of 20289-27-4 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; Brigham and Women’s Hospital, Inc.; President and Fellows of Harvard College; US2005/119260; (2005); 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

6958-37-8,6958-37-8, 5-Nitro-1H-indole-3-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 5-nitroindole-3-carboxylic acid (2.45 g, 12 mmol) in methanol (50 cm3) was added sulphuric acid (1 cm3) and the solution stirred at reflux for 6 hours. The solution was allowed to cool and then poured onto ice-water, neutralised with sodium bicarbonate and the product filtered to give a yellow solid, which was recrystallised from methanol as an off-white solid. Yield 1.76 g, 67%. mp 282-2840C. deltaH 3.85 (3H, s, OCH3), 7.65 (IH, d, J 9, H7), 8.08 (IH, dd, Ji 9, J2 2.3, H6), 8.35 (IH, s, H2), 8.83 (IH, d, J 2.3, H4), 8.5 (IH, s, NH). uv lambdamax/nm 320 (15000), 251 (32450), lambdamin/nm 284, 213; pH 12 lambdamax/nm 366 (13100), 271 (31500), 213 (48100). m/z 243.1 (M+Na)+. Accurate mass measurement on (M+Na)+ Ci0H8N2O4Na 243.0396, deviation -5.73 ppm.

6958-37-8 5-Nitro-1H-indole-3-carboxylic acid 248136, aindole-building-block compound, is more and more widely used in various fields.

Reference：
Patent; MEDICAL RESEARCH COUNCIL; WO2007/135380; (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

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.393553-57-6,6-Bromo-4-methoxy-1H-indole,as a common compound, the synthetic route is as follows.

To a solution of 6-bromo- 4-methoxy-lH-indole A.85 (2.117 g, 9.36 mmol) in DMF (46 mL) at room temperature was added Cs2CO3 (9.155 g, 28.1 mmol) followed by 4-chloropyrimidin-2-amine A.12 (1.456 g, 11.24 mmol) and the mixture was stirred at 80 0C for 21 hours. The mixture was poured into water (200 mL) and the aqueous layer was extracted with ethyl acetate (100 mL x 2). The combined organic layers were washed with brine (100 mL x 2), dried over Na2SO4, filtered, and concentrated under reduced pressure to give a brown solid. The product was purified by silica gel column chromatography using 65% ethyl acetate in hexane as eluent to give 4-(6- bromo-4-methoxy-lH-indol-l-yl)pyrimidin-2-amine A.134 (1.961 g, 65.6% yield) as an orange solid: 1H NMR (400 MHz, DMSO-d6) delta ppm 8.55 (1 H, s), 8.27 (1 H, d, J=5.9 Hz), 7.95 (1 H, d, J=4.0 Hz), 6.89 – 7.04 (4 H, m), 6.75 (1 H, d, J=3.7 Hz), 3.92 (3 H, s); Mass Spectrum (ESI) m/e = 319.0 [M+l (79Br)] and 321.0 [M+l (81Br)].

393553-57-6, 393553-57-6 6-Bromo-4-methoxy-1H-indole 24728034, aindole-building-block compound, is more and more widely used in various fields.

Reference：
Patent; AMGEN INC.; WO2009/158011; (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

434958-85-7,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.

To a solution of Intermediate 49 (3.00 g, 12.9 mmol, 1.0 eq) in anhydrous MeCN (13 mL) was added a solution of N-bromosuccinimide (2.53 g, 14.2 mmol, 1.1 eq) in anhydrous MeCN (130 mL) dropwise via cannula. After 1.5 h, addition was complete and the reaction mixture was stirred for a further 1 h. The reactionmixture was concentrated in vacuo and purified twice by silica gel chromatography using hexane/CH2CI2 (1 :0-1 .5:1) to yield Intermediate 50 as a white solid (605 mg, 15%).1H NMR (300MHz, DMSO-d5) oH. 9.95 (5, 1H), 7.78-7.91 (m, 1H), 7.61-7.73 (m, 1H), 6.97 (d, J=8.9 Hz, 1H), 6.50-6.59 (m, 1H), 1.54-1.70 (m, 9H).MS (E5) 311.9 (45%, [M-Hfl.

The synthetic route of 434958-85-7 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; KARUS THERAPEUTICS LTD; SHUTTLEWORTH, Stephen Joseph; SILVA, Franck Alexandre; CECIL, Alexander Richard Liam; ALEXANDER, Rikki Peter; GATLAND, Alice Elizabeth; FINNEMORE, Daniel John; (123 pag.)WO2017/29521; (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.923197-75-5,(6-Bromo-1H-indol-2-yl)methanol,as a common compound, the synthetic route is as follows.

To a suspension of (6-bromo-1H-indol-2-yl)methanol (696 mg, 3.00 mmol) in THF (25.0 mL) was added MnO2 (3.20 g, 37.0 mmol) at 0 C. The reaction mixture was stirred for 24 h at room temperature. The reaction mixture was filtered through Celite, and the filtrate was concentrated under reduced pressure to give the title compound (371 mg, 55%) as an orange solid: 1H NMR (500 MHz, CDCl3) delta 9.86 (s, 1H), 9.07 (br s, 1H), 7.64 (s, 1H), 7.61 (d, J=8.5 Hz, 1H), 7.29 (dd, J=8.5, 1.5 Hz, 1H), 7.24 (d, J=1.0 Hz, 1H)., 923197-75-5

The synthetic route of 923197-75-5 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; ALBANY MOLECULAR RESEARCH, INC.; US2012/157469; (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

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

In a 250 mL flask was placed terf-butyl 5-(benzyloxy)-1H-indole-1-carboxylate (3.3g, 14 mmol) in 100 mL of acetone. 1,3-Dibromopropane (5.74 mL, 56.6 mmol) wasadded, followed by cesium carbonate (5.5 g, 17 mmol). The reaction was heated toreflux for 5 h. The reaction was cooled to room temperature and diluted with water (200mL). The mixture was transferred to a separatory funnel and extracted with ethyl acetate(2 x 150 mL). The combined organics were dried (MgSO4), filtered, and evaporated.The residue was then purified via flash chromatography to provide 4.7 g of terf-butyl 5-(3-bromopropoxy)-1H-indole-1-carboxylate (94%). 1H-NMR (DMSO-d6) 5 7.99-7.89 (d, 1H),7.61 (s, 1H), 7.17 (s, 1H), 6.98-6.91, (d, 1H), 6.62 (s, 1H), 4.16-4.05 (t, 2H), 3.64 (t, 2H),2.37-2.20 (m, 2H). LCMS RT= 3.55 min; [M]+= 254.1.

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

Reference：
Patent; BAYER PHARMACEUTICALS CORPORATION; WO2005/51957; (2005); 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

59908-47-3, 5-Chloro-1-methyl-1H-indole-2-carboxylic acid is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,59908-47-3

Production Example 5-4tert-butyl 6-{[5-chloro-1-methyl-1H-indol-2-yl]carbonyl}amino)octahydroisoquinoline-2(1H)-carboxylate To a methanol solution (100 mL) of the compound obtained in Production example 5-3 (3.3 g), 10% palladium carbon (500 mg) was added, and the resulting solution was stirred overnight at room temperature under 1 atm hydrogen atmosphere. The reaction solution was filtered and the filtrate was concentrated under reduced pressure. To a DMF (70 mL) solution of the residue, commercially available 5-chloro-1-methyl-1H-indole-2-carboxylic acid (2.4 g), HATU (4.4 g) and subsequently diisopropylethylamine (4.1 mL) were added, and the resulting solution was stirred overnight at room temperature. Water was added to the reaction solution, and the solution was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1 to 1:2), whereby the title compound (3.2 g) was obtained as a single optically active isomer (the arrangement in the structural formula is a relative configuration).

As the paragraph descriping shows that 59908-47-3 is playing an increasingly important role.

Reference：
Patent; MSD K.K; US2012/28990; (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

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

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.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