4-Cyanophenylboronic acid → 4-(2-(4-(1H-benzo[d]imidazole-2-carbonyl)phenoxy)pyridin-3-yl)benzonitrile

Participants

Reaction Conditions

Reaction Steps

A glass microwave reaction vessel was charged with (1H-benzo[d]imidazol-2-yl)(4-(3-bromopyridin-2-yloxy)phenyl)methanone (0.1427 g, 0.36 mmol), 4-cyanophenylboronic acid (0.0760 g, 0.43 mmol), trans-dichlorobis(triphenyl-phosphine)palladium(ii) (0.0314 g, 0.029 mmol), and sodium carbonate monohydrate (0.13 mL, 1.8 mmol) in 1,2-dimethoxymethane (3 mL) and water (1 mL). The reaction mixture was stirred and heated in a Biotage™ Initiator™ microwave reactor at 135° C. for 10 min. The solvent was evaporated. The crude product was adsorbed onto a plug of silica gel and chromatographed through a Biotage™ pre-packed silica gel column (25M), eluting with a gradient of 10% to 80% ethyl acetate in hexane, to provide 4-(2-(4-(1H-benzo[d]imidazole-2-carbonyl)phenoxy)pyridin-3-yl)benzonitrile. MS (ESI, pos. ion) m/z: 417.5 (M+1). IC50 (uM) +++++.

Provenance & Evidence