Sodium borohydride → HCID 70008667, compound

Participants

Reaction Steps

Sodium borohydride (0.018 g, 0.466 mmol) was added to a suspension of 1-oxo-1,2,3,4-tetrahydro-[1,4]diazepino[6,7,1-hi]indole-7-carbaldehyde (Example 45, 0.050 g, 0.233 mmol) in 15 mL EtOH. The reaction mixture was refluxed for 1.5 h, cooled to rt and the solvent was evaporated. The residue was partitioned between 1% aq NaOH and EtOAc. The organic extract was dried over anhydrous MgSO4, filtered and evaporated to give a pale-yellow solid (88%): 1H NMR (DMSO-d6) δ 3.52-3.55 (m, 2H), 4.31 (bs, 2H), 4.63 (d, 2H, J=5.0 Hz), 4.84 (t, 1H, J=5.0 Hz), 7.12 (t, 1H, J=7.5 Hz), 7.29 (s, 1H), 7.80-7.83 (m, 2H), 8.24-8.26 (m, 1H). HRMS calcd for C12H12N2O2 (M+) 216.0899, found 216.0908. Anal. (C12H12N2O2.0.2H2O) C, H, N.

Provenance & Evidence