Hexane → tert-butyl 7-(benzyloxy)-9H-carbazol-2-ylcarbamate

Participants

Reaction Conditions

Reaction Steps

A suspension of tert-butyl 4′-(benzyloxy)-2′-nitrobiphenyl-4-ylcarbamate (740 mg, 1.67 mmol) in 2 mL of triethyl phosphite was heated at 145° C. for 15 h under Ar atmosphere and cooled to rt. It was added 10 mL of hexane and let sit for 10 min. Solid was collected via filtration and washed with ether/hexane (v:v 1/1, 10 mL) and dried under high vacuum to afford tert-butyl 7-(benzyloxy)-9H-carbazol-2-ylcarbamate as a off-white solid (480 mg, 74%). 1H NMR (400 MHz, CDCl3) δ 7.89 (s, 1H), 7.83-7.78 (m, 3H), 7.46 (d, J=7.2 Hz, 2H), 7.38 (m, 2H), 7.32 (d, J=7.2 Hz, 1H), 6.94 (d, J=2.0 Hz, 1H), 6.88 (dd, J=8.8, 2.4 Hz, 1H), 6.83 (dd, J=8.4, 2.0 Hz, 1H), 6.60 (s, 1H), 5.15 (s, 2H), 1.52 (s, 9H); MS (ESI) m/z 389 (M+H+).

Provenance & Evidence