Water → HCID 24954329, compound

Participants

Reaction Steps

To a solution of 2-(6-iodo-pyrazin-2-yl)-4-methyl-thiazole-5-carboxylic acid benzylamide (100 mg, 0.23 mmol, 1.0 equiv) in dimethyl ether (1 mL) was added Na2CO3 (49 mg, 0.46 mmol, 2.0 equiv), trans-2-(4-trifluoromethylphenyl)vinyl boronic acid (123 mg, 0.57 mmol, 2.5 equiv.), PdCl2(dppf) (17 mg, 0.02 mmol, 0.1 equiv) and water (0.1 mL) in a sealed tube. The reaction vessel was immersed in an oil bath preheated to 100° C. After stirring for 2 hr, the reaction mixture 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 afford 4-methyl-2-{6-[(E)-2-(4-trifluoromethyl-phenyl)-vinyl]-pyrazin-2-yl}-thiazole-5-carboxylic acid benzylamide (77 mg, 70%). 1H NMR (400 MHz, CD2Cl2) δ 9.23 (s, 1H), 8.68 (s, 1H), 7.87 (d, J=16.0 Hz, 1H), 7.75 (d, J=8.0 Hz, 2H), 7.66 (d, J=12.0 Hz, 2H), 7.37 (d, J=4.0 Hz, 4H), 7.28-7.36 (m, 1H), 7.28 (d, J=16.0 Hz, 1H), 6.25 (bs, 1H), 4.62 (d, J=4.0 Hz, 2H), 2.74 (s, 3H); HRMS (M+H)+=481.13.

Provenance & Evidence