Iodine → HCID 69700895, compound

Participants

Reaction Steps

To a pale-yellow solution of 3,4-dihydro-2H-[1,4]diazepino[6,7,1-hi]indol-1-one (Example 42, 0.051 g, 0.274 mmol) in 5 mL DMF was added KOH (0.058 g, 1.03 mmol) and iodine (0.139 g, 0.548 mmol) at rt. The reaction mixture was stirred at rt overnight, at which time solvent was removed in vacuo. The residue was taken up in EtOAc and washed with 0.1% aq sodium bisulfite, H2O and brine. The organic layer was dried over anhydrous MgSO4, filtered and concentrated to give 0.078 g (92%) of a pale-yellow solid: 1H NMR (DMSO-d6) δ 3.56-3.59 (m, 2H), 4.40 (m, 2H), 7.26 (t, 1H, J=7.5 Hz), 7.52 (d, 1H, J=7.5 Hz), 7.67 (s, 1H), 7.93 (d, 1H, J=7.5 Hz), 8.37 (t, 1H, J=5.3 Hz). HRMS calcd. for C11H9N2OI (M+) 311.9761, found 311.9776. Anal. (C11H9N2OI) C, H, N.

Provenance & Evidence