Triethylamine → HCID 23449993, compound

Participants

Reaction Steps

A solution of diphenylphosphoryl azide (3.19 g, 2.50 mL, 11.6 mmol) in toluene (3 mL) was added dropwise to a solution of 2-fluoro-3-methoxybenzoic acid (1.70 g, 10 mmol) and triethylamine (1.17 g, 1.62 mL, 11.6 mmol) in anhydrous bromobenzene (20 mL). The reaction mixture was stirred at room temperature for 30 minutes and heated at 95° C. for 20 minutes. The reaction was cooled to ambient temperature and a solution of 2,6-difluorobenzylamine (1.43 g, 10 mmol) in dichloromethane (5 mL) was added. The mixture was stirred at ambient temperature for half of an hour, filtered, and washed with dichloromethane and ether to give a white solid (2.36 g, 76.1%). 1H NMR (DMSO-d6) δ3.77 (s, 3H), 4.35 (d, J=5.4 Hz, 2H), 6.69-7.70 (m, 6H), 7.07 (br s, 1H), 8.29 (br s, 1H); MS (CI) m/z 311.0 (MH+).

Provenance & Evidence