Aniline → HCID 68621190, compound

Participants

Reaction Steps

To a solution of carboxylic acid 50h (310 mg, 1 mmol) in dichloromethane (5 mL) stirred at room temperature under nitrogen was added triethylamine (135 μL, 1 mmol), followed by BOP (442 mg, 1 mmol), aniline (108 μL, 1 mmol) and triethylamine (405 μL, 3 mmol). The resulting reaction mixture was stirred for 12 hours at room temperature. The solvent was removed and the mixture was quenched with water (5 mL), extracted with ethyl acetate (3×10 mL), dried (MgSO4), concentrated. Purification by flash silica gel chromatography (5% methanol in dichloromethane) followed by crystallization from acetone afforded the corresponding amide 80 (20% yield). 1H NMR: (300 MHz, CDCl3) δ 8.00 (m, 4H), 7.40-7.60 (m, 10H), 3.00 (m, 2H), 2.60 (m, 2H), 1.60 (m, 4H), 1.20 (m, 4H).

Provenance & Evidence