1,2-Dimethoxyethane → 6-(Trifluoromethyl)-4-(3,4,5-trifluorophenyl)-1,3-dihydro-2H-benzimidazol-2-one

Participants

Reaction Steps

A mixture of 4-bromo-6-trifluoromethyl-1,3-dihydrobenzoimidazol-2-one (1.12 g, 4 mmol, Example 6a), 3,4,5-trifluorophenylboronic acid (1.1 g, 6 mmol, Lancaster), PdCl2(PPh3)2 (35 mg, 0.05 mmol, Aldrich), Na2CO3H2O (1 g, 8 mmol), dimethoxyethane (7mL), H2O (3 mL) and EtOH (2 mL) was subjected to microwave irradiation at 120° C. with stirring for 10 min. Water (10 mL) was added and the mixture was extracted with EtOAc (2×20 mL). The combined organic phases were washed with brine (10 mL), dried over Na2SO4, and filtered. The filtrate was concentrated in vacuo, and the residue was purified by silica gel chromatography, eluting with 35% EtOAc/hexane to give the title compound as a light-brown solid. MS (ESI, pos. ion) m/z: 333 (M+1).

Provenance & Evidence