Ethyl Acetate → tert-Butyl 2-(6-chloronicotinamido)-4-(thiophen-2-yl)phenylcarbamate

Participants

Reaction Steps

A mixture of tert-butyl[2-amino-4-(2-thienyl)phenyl]carbamate (E) (600 mg, 2.07 mmol) and 6-chloronicotinyl chloride (380 mg, 2.16 mmol) in 5 mL of pyridine was stirred overnight, poured into EtOAc and washed with saturated NaHCO3, dried (Na2SO4) and concentrated giving the BOC-protected chloronicotinamide (F): 1H NMR (600 MHz, CD3OD): δ 8.95 (d, J=2.3 Hz, 1H), 8.35 (dd, J=8.2 Hz, 2.3 Hz, 1H), 7.85 (br s, 1H), 7.62 (d, J=8.5 Hz, 1H), 7.55-7.51 (m, 2H), 7.37-7.35 (m, 2H), 7.07 (dd, J=5.0 Hz, 3.5 Hz, 1H), 4.59 (s, 1H), 1.49 (s, 9H); MS (ESI+): cal'd [M+Na]+ 452.1, obs'd 452.1.

Provenance & Evidence