Hydrogen Bromide → 3-Amino-5-(4-methoxyphenyl)-1H-benzo[e][1,4]diazepin-2(3H)-one

Participants

Reaction Conditions

Reaction Steps

Intermediate 6B (1000 mg, 2.407 mmol) was treated with 33% HBr in acetic acid (5 mL) to give a suspension. The reaction mixture was then heated to 70° C. for 3 hrs with stirring. The reaction mixture was then poured into ether (100 mL). The resulting solid was filtered and then partitioned between DCM (100 mL)/saturated NaHCO3 (100 mL). The aqueous phase was back extracted with DCM (3×100 mL). The combined organic phases were dried with MgSO4, filtered and concentrated to provided Intermediate 6C (0.608 g, 90%). 1H NMR (400 MHz, DMSO-d6) δ 10.61 (br. s., 1H), 7.62-7.53 (m, 1H), 7.44 (d, J=8.8 Hz, 2H), 7.34-7.23 (m, 2H), 7.23-7.17 (m, 1H), 6.99 (d, J=9.0 Hz, 2H), 4.20 (s, 1H), 3.81 (s, 3H).

Provenance & Evidence