2-Iodoxybenzoic acid → HCID 70008467, compound

Participants

Reaction Steps

o-Iodoxybenzoic acid (Frigerio, et al., J. Org. Chem. 1995, 60, 7272) (2.217 mmol, 0.621 g) was added to a solution of 7-(1-Hydroxy-ethyl)-3,4-dihydro-2H-[1,4]diazepino[6,7,1-hi]indol-1-one (Example 163) (0.739 mmol, 0.170 g) in DMSO (8 mL) at rt. The reaction mixture was stirred at rt for 2.5 h. The solvent was removed in vacuo and the residue was taken up in EtOAc and washed with 5% Na2S2O3/5% NaHCO3, H2O and brine. The organic layer was dried over anhydrous MgSO4 and concentrated to give an orange solid. The solid was purified by flash silica gel chromatography eluting with a gradient of 0-5% MeOH in CHCl3 to give 0.094 g (75%) of a pale pink solid: mp=285-287° C.; 1H NMR (DMSO-d6) δ 2.42 (s, 3H), 3.56-3.61 (m, 2H), 4.44 (br s, 2H), 7.32 (t, 1H, J=6.0 Hz), 7.92 (d, 1H, J=6.0 Hz), 8.40-8.44 (m, 3H); HRMS calcd. for C13H12N2O2 (M+) 228.0899, found (M+) 228.0890; Anal. (C13H12N2O2) C, H, N.

Provenance & Evidence