Trifluoroacetic acid → HCID 66926921, compound

Participants

Reaction Steps

Trifluoroacetic acid (5 mL, 64.9 mmol) was added to a solution of 3-chloro-5-(4-(hydroxy(phenyl)methyl)phenyl)isonicotinonitrile (327 mg, 0.816 mmol, 80% pure) and triethylsilane (5 mL, 31.3 mmol) in dichloromethane (10 mL). After 1 h at room temperature, the mixture was concentrated, quenched with saturated sodium bicarbonate (30 mL) and extracted with dichloromethane (3×15 mL). The combined extracts were dried (MgSO4) and concentrated. Silica gel chromatography, loading with toluene and eluting with 10-30% ethyl acetate in hexanes, gave 3-(4-benzylphenyl)-5-chloroisonicotinonitrile as colorless liquid (195.2 mg, 79% yield). 1H NMR (400 MHz, CDCl3) δ ppm 8.74 (1H, s), 8.68 (1H, s), 7.45-7.58 (2H, m), 7.28-7.43 (4H, m), 7.15-7.28 (3H, m), 4.07 (2H, s). MS (ES+) m/z: 305 (M−H2O+H); LC retention time: 4.391 min (analytical HPLC Method A).

Provenance & Evidence