Sodium hydride → 4-Bromo-2-methylphenethyl 3-cyanophenylcarbamate

Participants

Reaction Conditions

Reaction Steps

NaH (150 mg, 60% disperson in oil) was added portionwise to a solution of 30B (570 mg, 2.65 mmol) in THF (26.5 mL) and the mixture was stirred for 30 min. The solution was cooled to −78° C. and 3-isocyanatobenzonitrile (382 mg, 2.65 mmol) was added in one portion. The cooling bath was removed and the reaction was stirred for 2 h. Water (100 mL) was added to the reaction mixture and it was extracted with EtOAc (2×75 mL). The organics were combined, 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 30C (590 mg, 62%). 1H NMR (400 MHz, DMSO-D6) δ ppm 2.30 (s, 3 H) 2.92 (t, J=6.95 Hz, 2 H) 4.28 (t, J=6.95 Hz, 2 H) 7.17 (d, J=8.34 Hz, 1 H) 7.32 (dd, J=8.21, 1.89 Hz, 1 H) 7.39 (d, J=1.77 Hz, 1 H) 7.41-7.55 (m, 2 H) 7.70 (d, J=8.08 Hz, 1 H) 7.85 (s, 1 H) 9.97 (s, 1 H).

Provenance & Evidence