Sodium hydride → 4-Bromo-2-methylphenethyl 3-cyano-4-(ethylsulfonyl)phenylcarbamate

Participants

Reaction Conditions

Reaction Steps

NaH (230 mg, 4.4 mmol, 60% disperson in oil) was added portionwise to a solution of 30B (490 mg, 2.3 mmol) in THF (12 mL) and the mixture was stirred for 30 min. The solution was cooled to −40° C. and 25A (760 mg, 2.3 mmol) was added in one portion. The cooling bath was removed and the reaction was stirred for 2 h. The reaction mixture was cooled to −40° C. and quenched by the addition of NH4Cl (5 mL, sat. aq.). The resulting mixture was partitioned between water (50 mL) and EtOAc (100 mL). The organic phase washed with brine, dried over Na2SO4 and concentrated in vacuo. The crude product was purified by flash chromoatography (0 to 100% EtOAc in hexanes) to yield 31A (745 mg, 72%) as a white solid. 1H NMR (400 MHz, MeOD) δ ppm 1.94 (t, J=7.42 Hz, 3 H) 3.11 (s, 3 H) 4.19 (q, J=7.15 Hz, 2 H) 5.14 (t, J=6.87 Hz, 2 H) 7.99 (d, J=8.24 Hz, 1 H) 8.14 (dd, J=7.70, 2.20 Hz, 1 H) 8.21 (d, J=1.65 Hz, 1 H) 8.72-8.77 (m, 1 H) 8.79-8.84 (m, 1 H) 8.90 (d, J=2.20 Hz, 1 H).

Provenance & Evidence