Potassium Hydroxide → tert-Butyl 4-(((5-amino-4'-cyanobiphenyl-3-yl)methoxy)methyl)-4-phenylpiperidine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

tert-Butyl 4-((3-amino-5-bromobenzyloxy)methyl)-4-phenylpiperidine-1-carboxylate (220.0 mg, 0.46 mmol), 4-cyanophenylboronic acid (273.0 mg, 1.86 mmol), and tetrakis(triphenylphosphine) palladium(0) (71.7 mg, 0.046 mmol) were combined in dry tetrahydrofuran (5 mL) in a microwave tube and sealed. The mixture was flushed with nitrogen. To this was added potassium hydroxide (1 N in water, 1.4 mL, 1.4 mmol). The mixture was heated at 120° C. for 1 h via microwave. After cooling to room temperature, the reaction mixture was concentrated and purified by flash chromatography on silica gel (25% ethyl acetate/hexanes) to afford 140.0 mg (61%). LC/MS (HPLC method 3): tR=2.85 min, 498.24 (MH)+.

Provenance & Evidence