Acetic Anhydride → HCID 66926900, compound

Participants

Reaction Steps

Hunig's base (0.045 mL, 0.256 mmol) was added to a mixture of 2-(3-(aminomethyl)phenyl)-3-fluoro-5-(4-phenoxyphenyl)isonicotinonitrile bis-HCl salt (12 mg, 0.026 mmol) and acetic anhydride (0.012 mL, 0.128 mmol) in dichloromethane (3 mL). After 1 h at room temperature, the mixture was diluted with brine (10 mL), water (10 mL) and extracted with dichloromethane (3×10 mL). The combined extracts were dried (MgSO4) and concentrated. Silica gel chromatography, loading with dichloromethane and eluting with 50-100% ethyl acetate in hexanes, gave N-(3-(4-cyano-3-fluoro-5-(4-phenoxyphenyl)pyridin-2-yl)benzyl)acetamide as off-white solid (10.2 mg, 91% yield), 1H NMR (500 MHz, CDCl3) δ ppm 8.73 (1H, s), 7.89-7.98 (2H, m), 7.57-7.66 (2H, m), 7.47-7.55 (1H, m), 7.37-7.47 (3H, m), 7.18-7.25 (1H, m), 7.14-7.18 (2H, m), 7.12 (2H, δ, J=7.70 Hz), 5.87 (1H, br. s), 4.55 (2H, δ, J=5.77 Hz), 2.07 (3H, s); MS (ES+) m/z: 438 (M+H); LC retention time: 4.388 min (analytical HPLC Method A).

Provenance & Evidence