Cyclobutylamine → HCID 89782174, compound

Participants

Reaction Conditions

Reaction Steps

Propylphosphonic anhydride solution (T3P; Alfa Aesar, Ward Hill, Mass.; ≧50 wt % in EtOAc; 6.06 mL, 10.18 mmol) was added (dropwise, over 1 min) to a suspension of 2-amino-3-bromobenzoic acid (Aldrich; 2.00 g, 9.26 mmol) and cyclobutylamine (Aldrich; 2.37 mL, 27.8 mmol) in EtOAc (20 mL) at 0° C. The resulting solution was warmed to 23° C. and stirred for 1.5 h Additional propylphosphonic anhydride solution (≧50 wt % in EtOAc; 1.21 mL, 2.04 mmol) and cyclobutylamine (0.790 mL, 9.27 mmol) were sequentially added, and the resulting mixture was stirred at 23° C. for 3 h. The reaction mixture was then partitioned between EtOAc (100 mL) and saturated aqueous NaHCO3 (100 mL). The organic layer was separated, sequentially washed with saturated aqueous NaHCO3 (2×50 mL), and brine (50 mL), dried over Na2SO4, filtered, and concentrated in vacuo to give 2-amino-3-bromo-N-cyclobutylbenzamide (2.127 g, 7.90 mmol, 85% yield) as a light-yellow solid: 1H NMR (400 MHz, CDCl3) δ ppm 7.50 (1H, dd, J=7.8, 1.2 Hz), 7.27 (1H, d, J=7.8 Hz), 6.52 (1H, t, J=7.8 Hz), 6.12 (2H, br. s.), 5.81-6.06 (1H, m), 4.53 (1H, sxt, J=8.0 Hz), 2.35-2.53 (2H, m), 1.90-1.98 (2H, m), 1.74-1.82 (2H, m). m/z (ESI, +ve) 268.9/271.0 (M+H)+.

Provenance & Evidence