Tag: M.W:200-300

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

1-(tert-Butoxycarbonyl)-5-hydroxyindole (2.33 g, 10.0 mmol) and triphenylphosphine (5.25 g, 20.0 mmol) were dissolved in toluene (46.0 mL), and the solution was added with glycidol (1.32 mL, 20.0 mmol) and 40% DEAD-toluene solution (9.10 mL, 20 mmol) at room temperature, followed by stirring at 80C for 4 hours. The solvent was evaporated under reduced pressure and the residue was purified by flash column chromatography (hexane/ethyl acetate=4/1). A crude product (1.28 g) of 1-(tert-butoxycarbonyl)-5-hydroxyindole (1.28 g) was obtained. The obtained crude product was dissolved in N,N-dimethylacetoamide (20.0 mL), and the solution was added with 2- (ethylamino) ethanol (8.60 mL, 87.8 mmol), followed by stirring at 80C for 4 hours. The reaction mixture was added with water and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by flash column chromatography (chloroform/methanol =9/1) to obtain 1-(tert-butoxycarbonyl)-5-{3-[N-ethyl(2-hydroxyethyl)amino]-2-hy droxypropoxy}indole (1.53 g, 40%). ESI-MS m/z: 379 [M+H]+; 1H-NMR (CDCl3)delta(ppm): 1.07 (t, J = 7.2 Hz, 3H), 1.66 (s, 9H), 2.61-2.80 (m, 6H), 3.61-3.68 (m, 2H), 3.99-4.14 (m, 3H), 6.48 (d, J = 3.9 Hz, 1H), 6.94 (dd, J = 2.6, 8.7 Hz, 1H), 7.04 (d, J = 2.6 Hz, 1H), 7.56 (d, J = 3.9 Hz, 1H), 8.01 (d, J = 8.7 Hz, 1H).

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

Reference：
Patent; Kyowa Hakko Kirin Co., Ltd.; EP2108642; (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

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.312314-26-4,4-(Benzyloxy)-6-fluoro-1H-indole,as a common compound, the synthetic route is as follows.

To a solution of compound l-5b (559 mg, 2.32 mmol) in 70 mL ether, oxalyl chloride was added slowly at O C. After 10 min, the reaction mixture was warmed to room temperature and stirred for 6 h. After the mixture was cooled to O C, Et3N (3.0 mL) and MeOH (3.0 mL) were introduced and the resulting mixture was stirred overnight. The reaction mixture was diluted with water and extracted with EtOAc 2 X 100 mL, the combined organic phase was washed by brine and dried over Na2SO4. After concentration, the crude product 26-1 was obtained as a brown oil (897 mg), which was used in the next step without purification. 1H NMR (CDCl3, 300 MHz) delta (ppm): 9.09 (bs, 1H), 8.00 (d, J=3.0Hz, 1H), 7.50 (d, J=7.1Hz, 2H), 7.28-7.41 (m, 3H), 6.72 (dd, J=1.9, 8.3Hz, 1H), 6.51 (dd, J=1.9, 11.7Hz, 1H), 5.20 (s, 2H), 3.67 (s, 3H)., 312314-26-4

312314-26-4 4-(Benzyloxy)-6-fluoro-1H-indole 10610125, aindole-building-block compound, is more and more widely used in various fields.

Reference：
Patent; GALENEA CORPORATION; ELDER, Amy; HARRIMAN, Geraldine; LEIT, Silvana; LI, Jie; SARD, Howard; ZHANG, Yiliang; WILSON, Doug; WO2011/19738; (2011); 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

72016-68-3,72016-68-3, Ethyl 2-(5-bromo-2-methyl-1H-indol-3-yl)acetate is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step 2 Ethyl 2-(5-bromo-1-(4-iodobenzyl)-2-methyl-1H-indol-3-yl)acetate To a solution of the product of Step 1 (536.2 mg, 2 mmol) and 4-iodobenzyl chloride (504 mg, 2 mmol) in dry DMF (10 mL) at 0 C. was added sodium hydride (80 mg, 2 mmol, 60% in oil). The mixture was stirred at 20 C. for 20 hours and a saturated NH4 Cl solution (10 mL) was added. The mixture was extracted with EtOAc, the extracts were dried over MgSO4 and concentrated to an oil. The oil was purified by flash chromatography on silica gel, eluding with 20% EtOAc in hexane to afford 704 mg (69%) of the title compound. 1 H NMR (CDCl3) 1.23 (3H, t, J=7.1 Hz), 2.28 (3H, s), 3.65 (2H, s), 4.12 (2H, q, J=7.1 Hz), 5.19 (2H, s), 6.64 (2H, d, J=8.3 Hz), 6.98 (1H, d, J=8.6 Hz), 7.17 (1H, dd, J=8.6 Hz, 1.8 Hz), 7.56 (2H, d, J=8.3 Hz), 7.68 (1H, d, 1.8 Hz).

The synthetic route of 72016-68-3 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; Merck Frosst Canada, Inc.; US5510368; (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

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 l-chloro-5H-pyrido[4,3-6]indole-4-carboxamide in cone. NH4OH (0.07 M) was heated in a microwave reactor at 1600C for 1 h in a sealed tube. The reaction mixture was cooled to room temperature and partitioned between THF/EtOAc and saturated NaHCO3. After separation of the organic phase, the aqueous phase was extracted again with THF/EtOAc, and the combined organic phases were washed with brine, dried over Na2SCXj and filtered. After evaporation of the organic solvents, the residue was purified by flash chromatography (0-10% MeOH in EtOAc) to provide the title compound as an off-white solid.1H NMR (DMSO-d6) delta 11.50 (IH, s), 8.50 (IH, s), 8.30 (IH, d), 7.85 (IH, br s), 7.75 (IH, d), 7.35 (IH, t), 7.20 (IH, t), 7.15 (IH, br s), 6.80 (2H, br s).

The synthetic route of 938465-52-2 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; MERCK & CO., INC.; MERCK FROSST CANADA LTD.; WO2007/61764; (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.1186663-64-8,3-Bromo-1H-indole-4-carbonitrile,as a common compound, the synthetic route is as follows.

3-Bromo?l H-mdole-4-carboimrile (l-146a: 5OU mg, 2.272 mmol) was added dropwise. tupsilon a stirred mixture of NaI 1 (0.218 g, 9.0833 mmol) in dry DMl- ( 15 ml ) at OT over a period of 10 minutes. This was followed b>- the addition of methyl iodide and the resulting mixture was stirred at O0C for -? hours. The reaction was monitored by Tl, C (10% cth) lacctatc in hcxane). The reaction mixture was quenched with ice water: the precipitate formed was collected and dried to afford 0.400 g of the crude product.1H NMR (CDCl,, 300 MH/): delta 7.8-7.0 (m, 411), 3.82 (s, 3H)

1186663-64-8, The synthetic route of 1186663-64-8 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; NOVARTIS AG; BOCK, Mark G.; GAUL, Christoph; GUMMADI, Venkateshwar Rao; SENGUPTA, Saumitra; WO2010/149755; (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

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

General procedure: To a solution of 1a (196 mg, 1.00 mmol) in DMF (3.30 mL) were added HOBt·H2O (149 mg, 1.10 mmol), EDCI·HCl (211 mg, 1.10 mmol), 2,2,6,6-tetramethylpiperidin-4-amine (156 muL, 900 mumol) and Et3N (152 muL, 1.10 mmol) at 0 C. The reaction mixture was heated to room temperature and stirred for 20 h. The reaction was quenched with saturated aqueous NaHCO3 solution and extracted with CHCl3. The extract was washed with brine and dried over MgSO4. Concentration under reduced pressure provided the title compound 9a (210 mg, 74% yield) as a white powder., 59908-47-3

The synthetic route of 59908-47-3 has been constantly updated, and we look forward to future research findings.

Reference：
Article; Kobayakawa, Takuya; Ohashi, Nami; Hirota, Yuki; Takahashi, Kohei; Yamada, Yuko; Narumi, Tetsuo; Yoshimura, Kazuhisa; Matsushita, Shuzo; Harada, Shigeyoshi; Tamamura, Hirokazu; Bioorganic and Medicinal Chemistry; vol. 26; 21; (2018); p. 5664 – 5671;,
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

16732-69-7, Ethyl 7-bromo-1H-indole-2-carboxylate is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step 1 S-Benzoyl^-bromo-lH-indole^-carboxylic acid ethyl ester To a solution of 7-bromo-lH-indole-2-carboxylic acid ethyl ester (2.04 g, 7.6 mmol) in 1,2- dichloroethane (60 ml) were added AICI3 (2.0 g, 15.0 mmol) and benzoic anhydride (3.45 g, 15.2 mmol). After heating at 9O0C for 2 hours, the reaction mixture was poured into a mixture OfEtOAcZH2O. The organic fraction was separated and washed with water and brine. After drying over MgSO4, the organic fraction was concentrated in vacuo and the resulting residue was purified by flash chromatography to give b-Benzoyl-7-bromo-lH- indole -2 -carboxylic acid ethyl ester as yellow solid (-100%). MS: (M+H)+ 374.1.

16732-69-7, As the paragraph descriping shows that 16732-69-7 is playing an increasingly important role.

Reference：
Patent; F. HOFFMANN-LA ROCHE AG; WO2008/55808; (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

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

100 mg (0.4 mmol) of 5-hydroxy-1-tert-butyl ester-1H-indole (a) was dissolved in 1 ml of DMF, and 0.5 ml (4 mmol) of p-fluoroacetophenone and 0.96 g (0.8 mmol) were added.Potassium tert-butoxide, stirred at 100 C for 7 hours, diluted with water, extracted with EA,Wash with saturated sodium chloride, dry over anhydrous sodium sulfate, concentrate under reduced pressure, and thenPE: EA=150:1 to get an oil,The yield was 46%.

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

Reference：
Patent; Tianjin University of Science and Technology; Yu Peng; Guo Na; Lv Hongbin; Fu Ying; Teng Yuou; Wang Dong; (32 pag.)CN110229091; (2019); 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

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

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.14618-45-2,3-(Trifluoroacetyl)indole,as a common compound, the synthetic route is as follows.

General procedure for preparation of XY; A solution of XInt01 (1 eq), K2CO3 (5 eq) and alkyl halides Y such as methyl iodide, ethyl iodide, n-propyl bromide, iso-propyl bromide, n-butyl bromide, isobutyl bromide (1.5 eq, 1 h) or O-t-butyldimethylsilyl-2-chloroethanol (10 eq, 24 h) or O-t-butyldimethylsilyl-2-chloropropanol in acetone was stirred and heated to reflux. After completion of the reaction (monitored by thin layer chromatography (TLC)), the mixture was concentrated in vacuo and the residue treated with dichloromethane. The insoluble impurities were removed by filtration and the filtrate was concentrated to afford compound XY (60-95% yield).; Example 6; N-(cyclopentylmethyl)-1-methyl-1H-indole-3-carboxamide; Synthesised according to the procedure disclosed in Example 1 where X is indole, Y is methyl iodide and Z is cyclopentylmethyl amine. Formula: C16H20N2O; Molecular Weight: 256.3; Mass/charge ratio: 256.2 (100.0%), 257.2 (18.3%), 258.2 (1.8%); Elemental analysis: C, 74.97; H, 7.86; N, 10.93; O, 6.24.

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

Reference：
Patent; AFFECTIS PHARMACEUTICALS AG; US2009/312366; (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