107516-75-6 | - Indole Building Blocks

Analyzing the synthesis route of 107516-75-6

The synthetic route of 107516-75-6 has been constantly updated, and we look forward to future research findings.

107516-75-6, Diethyl 1H-indole-2,6-dicarboxylate is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

b: 1-(Cyano-methyl-methyl)-1H-indole-2,6-dicarboxylic acid diethyl ester A mixture of K2CO3 (7.93 g, 57.0 mmol) and 1H-indole-2,6-dicarboxylic acid diethyl ester (5.0 g, 19.14 mmol) in DMF (30 mL) was stirred at room temperature for 0.5 h. Then 2-bromo-propionitrile (3.4 mL, 38.3 mmol) in DMF (10 mL) was added. The reaction was warmed to 80 C. and kept at this temperature for 6 h. Then the reaction was cooled down to the room temperature. Most of the DMF solvent was removed in vacuo and the crude residue was extracted several times with EtOAc. The combined organic extracts were washed with brine, dried over MgSO4 and concentrated. The crude product was triturated with MeCN to give 3.9 g of 1-(cyano-methyl-methyl)-1H-indole-2,6-dicarboxylic acid diethyl ester as a white fluffy solid. The filtrate was concentrated and purification by silica gel chromatography provided 1.6 g of 1-(cyano-methyl-methyl)-1H-indole-2,6-dicarboxylic acid diethyl ester, yield 91%., 107516-75-6

The synthetic route of 107516-75-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Boehringer Ingelheim Pharmaceuticals, Inc.; US2006/276453; (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

Downstream synthetic route of 107516-75-6

107516-75-6, As the paragraph descriping shows that 107516-75-6 is playing an increasingly important role.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.107516-75-6,Diethyl 1H-indole-2,6-dicarboxylate,as a common compound, the synthetic route is as follows.

Step 5: Synthesis of diethyl l-{(2S)-4-[(tert-butoxycarbonyl)amino]butan-2-yl}-1H- indole-2,6-dicarboxylateTo a suspension of hexane washed 60% sodium hydride in mineral oil (91 mg, 2.3 mmol) in DMF (2.5 mL) under nitrogen atmosphere to 0 C is added a solution of diethyl 1H- indole-2,6-dicarboxylate (619 mg, 2.4 mmol) in DMF (4 mL). The mixture is stirred for 20 min at 0 C and a solution of tert-butyl (6R)-6-methyl-1,2,3-oxathiazinane-3- carboxylate 2,2-dioxide (518 mg, 2.1 mmol) in DMF (2.5 mL) is added. The reaction mixture is stirred for 30 min at 0 C and is warmed to room temperature and stirred for 72 h. Water and NH4C1 solution are added and the mixture is stirred for 15 min. The aqueous mixture is extracted with EtOAc (50 mL) and the organic layer is washed with water, brine, dried (MgS04) and concentrated to afford the title crude compound (1.1 g) which is used in the next step without purification.

107516-75-6, As the paragraph descriping shows that 107516-75-6 is playing an increasingly important role.

Reference£º
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BOYER, Stephen, James; GAO, Donghong, Amy; GUO, Xin; KIRRANE, Thomas, Martin, Jr.; SARKO, Christopher, Ronald; SNOW, Roger, John; SOLEYMANZADEH, Fariba; ZHANG, Yunlong; WO2011/71716; (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

Analyzing the synthesis route of 107516-75-6

107516-75-6, The synthetic route of 107516-75-6 has been constantly updated, and we look forward to future research findings.

107516-75-6, Diethyl 1H-indole-2,6-dicarboxylate is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step 2: Synthesis of diethyl l-{3-[(tert-butoxycarbonyl)amino]-2,2-dimethylpropyl}- 1H-indole-2,6-dicarboxylate To a solution of diethyl 1H-indole-2,6-dicarboxylate (25.3 g, 97 mmol), tert-butyl (3- hydroxy-2,2-dimethylpropyl)carbamate (19.7, 97 mmol) and triphenylphosphine (50.9 g, 194 mmol) in THF (200 mL) is added and diisopropyl azodicarboxylate (40.2 mL, 194 mmol). The mixture is stirred for 60 h at room temperature and then the solvent is removed. The residue is separated into two portions and each of them is filtered through a short plug of silica gel (400 g) using 20% EtOAc in heptane. A mixture of diethyl l-{3- [(tert-butoxycarbonyl)amino]-2,2-dimethylpropyl}-1H-indole-2,6-dicarboxylate and diethyl 1H-indole-2,6-dicarboxylate (55 g) is obtained and the mixture is used in the next step without further purification.

107516-75-6, The synthetic route of 107516-75-6 has been constantly updated, and we look forward to future research findings.

Brief introduction of 107516-75-6

107516-75-6, The synthetic route of 107516-75-6 has been constantly updated, and we look forward to future research findings.

Example 5 Synthesis of (R)-3-aminomethyl-1-oxo-1,2,3,4-tetrahydro-pyrazino[1,2-a]indole-7-carboxylic acid pyridin-3-ylamide A mixture of K2CO3 (1.06 g, 7.65 mmol) and 1H-indole-2,6-dicarboxylic acid diethyl ester (1.0 g, 3.8 mmol) in DMF (15 mL) was stirred at room temperature for 0.5 h. Then toluene-4-sulfonic acid (S)-2,2-dimethyl-[1,3]dioxolan-4-yl methyl ester (1.20 g, 4.2 mmol) in DMF (5 mL) was added. The reaction mixture was warmed to 100 C. and kept at this temperature overnight. The reaction was concentrated and the residues were extracted with EtOAc several times. The combined organic extracts were washed with brine, dried over MgSO4 and concentrated. Purification by silica gel chromatography gave 1.34 g of 1-((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-1H-indole-2,6-dicarboxylic acid diethyl ester as white solid, yield 93%. ESI-MS m/z 376.42 [M+H]+.

107516-75-6, The synthetic route of 107516-75-6 has been constantly updated, and we look forward to future research findings.