Sodium hydride → HCID 86644969, compound

Participants

Reaction Conditions

Reaction Steps

NaH (60% dispersion in mineral oil; 33 mg, 0.82 mmol, 1.05 equiv) was added to a stirred solution of N-(allyloxy)-4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxy-phenyl)picolinamide (300 mg, 0.78 mmol, 1.0 equiv) in THF (7.8 mL) at 23° C. The vigorously bubbling off-white mixture was stirred at 23° C. for 1 h. The resulting homogeneous light tan solution was concentrated via rotary evaporation. The residue was slurried in hexane and vacuum filtered to afford an off-white powder (260 mg, 81%): mp 236-240° C. dec; 1H NMR (300 MHz, DMSO-d6) δ 7.59 (dd, J=9, 8 Hz, 1H), 7.34 (dd, J=9, 2 Hz, 1H), 7.00 (d, J=2 Hz, 1H), 6.18 (br s, 2H), 6.01 (m, 1H), 5.18 (m, 1H), 5.03 (m, 1H), 4.13 (m, 2H), 3.92 (d, J=1 Hz, 3H).

Provenance & Evidence