Category: 153374-33-5

Electric Literature of 153374-33-5, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 153374-33-5, name is 1-Methyl-1H-pyrrolo[3,2-b]pyridine, molecular formula is C8H8N2, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

General procedure: To a solution of 14a-d (2.5 mmol) in anhydrous dichloromethane (10 mL) anhydrous aluminum chloride (1.2 g, 8.8 mmol) was slowly added. The reaction mixture was stirred at room temperature (in the case of 15b) or heated under reflux for 10 min (in the case of 15a,c,d) and bromoacetyl bromide (0.2 mL, 2.5 mmol) in dichloromethane (2 mL) was added dropwise. The resulting solution was allowed to stir under reflux for 15-40 min. After cooling, water and ice were slowly added and the obtained precipitate was filtered off and purified by column chromatography using ethyl acetate (for compounds 15a, c) or dichloromethane/ethyl acetate (95/5) (for compound 15b,d) as eluent. For compounds 15b-d see supplementary material.

According to the analysis of related databases, 153374-33-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Carbone; Pennati; Barraja; Montalbano; Parrino; Spano; Lopergolo; Sbarra; Doldi; Zaffaroni; Cirrincione; Diana; Current Medicinal Chemistry; vol. 21; 14; (2014); p. 1654 – 1666;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 153374-33-5, name is 1-Methyl-1H-pyrrolo[3,2-b]pyridine, molecular formula is C8H8N2, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below. Recommanded Product: 153374-33-5

The reaction was conducted according to the General Procedure by heating KOt-Bu (4.5 mg, 0.04 mmol, 20 mol%), N-methyl- 4-azaindole 3a (26.4 mg, 0.2 mmol, 1 equiv), Et3SiH (98 muL, 0.6 mmol, 3 equiv) and 0.2 mL of THF at 45 C for 96 h. C2:C3 = 6:1. A mixture of C2- and C3-silylation products (16.2 mg, 33% yield) was obtained after purification by silica gel flash chromatography (50% EtOAc in hexanes). Analytically pure C2-silylation 4a was obtained as a colorless oil after subsequent purification by Preparative TLC (50% EtOAc in hexanes). Rf = 0.1 (33% EtOAc in hexanes); 1H NMR (500 MHz, CDCl3) delta 8.44 (dd, J = 4.6, 1.4 Hz, 1H), 7.60 (dt, J = 8.3, 1.2 Hz, 1H), 7.09 (dd, J = 8.3, 4.6 Hz, 1H), 6.90 (d, J = 0.9 Hz, 1H), 3.83 (s, 3H), 1.03- 0.97 (m, 9H), 0.96- 0.89 (m, 6H); 13C NMR (125 MHz, CDCl3) delta 147.0, 143.0, 142.7, 133.0, 116.4, 116.1, 113.8, 33.1, 7.6, 4.0. IR (Neat Film, NaCl) 2953, 2909, 2874, 1596, 1557, 1455, 1434, 1413, 1355, 1317, 1288, 1237, 1134, 1064, 1004, 800 cm-1; HRMS (ESI+) calc?d for C14H23N2Si [M+H]+: 247.1625, found 247.1621.

With the rapid development of chemical substances, we look forward to future research findings about 153374-33-5.

Reference:
Patent; CALIFORNIA INSTITUTE OF TECHNOLOGY; STOLTZ, Brian, M.; GRUBBS, Robert, H.; FEDOROV, Alexey; TOUTOV, Anton; LIU, Wenbo; BETZ, Kerry; (129 pag.)WO2016/22624; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 153374-33-5, name is 1-Methyl-1H-pyrrolo[3,2-b]pyridine, molecular formula is C8H8N2, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below. Recommanded Product: 153374-33-5

The reaction was conducted according to the General Procedure by heating KOt-Bu (4.5 mg, 0.04 mmol, 20 mol%), N-methyl- 4-azaindole 3a (26.4 mg, 0.2 mmol, 1 equiv), Et3SiH (98 muL, 0.6 mmol, 3 equiv) and 0.2 mL of THF at 45 C for 96 h. C2:C3 = 6:1. A mixture of C2- and C3-silylation products (16.2 mg, 33% yield) was obtained after purification by silica gel flash chromatography (50% EtOAc in hexanes). Analytically pure C2-silylation 4a was obtained as a colorless oil after subsequent purification by Preparative TLC (50% EtOAc in hexanes). Rf = 0.1 (33% EtOAc in hexanes); 1H NMR (500 MHz, CDCl3) delta 8.44 (dd, J = 4.6, 1.4 Hz, 1H), 7.60 (dt, J = 8.3, 1.2 Hz, 1H), 7.09 (dd, J = 8.3, 4.6 Hz, 1H), 6.90 (d, J = 0.9 Hz, 1H), 3.83 (s, 3H), 1.03- 0.97 (m, 9H), 0.96- 0.89 (m, 6H); 13C NMR (125 MHz, CDCl3) delta 147.0, 143.0, 142.7, 133.0, 116.4, 116.1, 113.8, 33.1, 7.6, 4.0. IR (Neat Film, NaCl) 2953, 2909, 2874, 1596, 1557, 1455, 1434, 1413, 1355, 1317, 1288, 1237, 1134, 1064, 1004, 800 cm-1; HRMS (ESI+) calc?d for C14H23N2Si [M+H]+: 247.1625, found 247.1621.

With the rapid development of chemical substances, we look forward to future research findings about 153374-33-5.

Reference:
Patent; CALIFORNIA INSTITUTE OF TECHNOLOGY; STOLTZ, Brian, M.; GRUBBS, Robert, H.; FEDOROV, Alexey; TOUTOV, Anton; LIU, Wenbo; BETZ, Kerry; (129 pag.)WO2016/22624; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 153374-33-5, name is 1-Methyl-1H-pyrrolo[3,2-b]pyridine, molecular formula is C8H8N2, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below. Recommanded Product: 153374-33-5

The reaction was conducted according to the General Procedure by heating KOt-Bu (4.5 mg, 0.04 mmol, 20 mol%), N-methyl- 4-azaindole 3a (26.4 mg, 0.2 mmol, 1 equiv), Et3SiH (98 muL, 0.6 mmol, 3 equiv) and 0.2 mL of THF at 45 C for 96 h. C2:C3 = 6:1. A mixture of C2- and C3-silylation products (16.2 mg, 33% yield) was obtained after purification by silica gel flash chromatography (50% EtOAc in hexanes). Analytically pure C2-silylation 4a was obtained as a colorless oil after subsequent purification by Preparative TLC (50% EtOAc in hexanes). Rf = 0.1 (33% EtOAc in hexanes); 1H NMR (500 MHz, CDCl3) delta 8.44 (dd, J = 4.6, 1.4 Hz, 1H), 7.60 (dt, J = 8.3, 1.2 Hz, 1H), 7.09 (dd, J = 8.3, 4.6 Hz, 1H), 6.90 (d, J = 0.9 Hz, 1H), 3.83 (s, 3H), 1.03- 0.97 (m, 9H), 0.96- 0.89 (m, 6H); 13C NMR (125 MHz, CDCl3) delta 147.0, 143.0, 142.7, 133.0, 116.4, 116.1, 113.8, 33.1, 7.6, 4.0. IR (Neat Film, NaCl) 2953, 2909, 2874, 1596, 1557, 1455, 1434, 1413, 1355, 1317, 1288, 1237, 1134, 1064, 1004, 800 cm-1; HRMS (ESI+) calc?d for C14H23N2Si [M+H]+: 247.1625, found 247.1621.

With the rapid development of chemical substances, we look forward to future research findings about 153374-33-5.

Reference:
Patent; CALIFORNIA INSTITUTE OF TECHNOLOGY; STOLTZ, Brian, M.; GRUBBS, Robert, H.; FEDOROV, Alexey; TOUTOV, Anton; LIU, Wenbo; BETZ, Kerry; (129 pag.)WO2016/22624; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem