反应详情

Part C. To a solution of 2-(6-iodo-pyrazin-2-yl)-4-methyl-thiazole-5-carboxylic acid benzylamide (70 mg, 0.16 mmol, 1.0 equiv) in dimethyl ether (1 mL) was added Na2CO3 (34 mg, 0.32 mmol, 2.0 equiv), benzyl boronic acid pinacol ester (87 μL, 0.40 mmol, 2.5 equiv), PdCl2(dppf) (11 mg, 0.02 mmol, 0.1 equiv) and water (0.1 mL) in a sealed tube. The reaction was immersed in an oil bath preheated to 100° C. After stirring for 4 hr, the reaction was cooled and the solvent was removed in vacuo. The crude product was purified by column chromatography [SiO2, methanol/dichloromethane, 0:100 to 10:90, v/v] and recrystallization (methanol/pentane) to give 2-(6-benzyl-pyrazin-2-yl)-4-methyl-thiazole-5-carboxylic acid benzylamide (41 mg, 65%). 1H NMR (400 MHz, CD2Cl2) δ 9.17 (s, 1H), 8.47 (s, 1H), 7.22-7.37 (m, 10H), 6.23 (bs, 1H), 4.59 (d, J=8.0 Hz, 2H), 4.19 (s, 2H), 2.72 (s, 3H); HRMS (M+H)+=401.14.

1. customThe reaction was immersed in an oil bath
2. custompreheated to 100° C
3. temperaturethe reaction was cooled
4. customthe solvent was removed in vacuo
5. customThe crude product was purified by column chromatography [SiO2, methanol/dichloromethane, 0:100 to 10:90
6. customv/v] and recrystallization (methanol/pentane)