Water → HCID 11315058, compound

Participants

Reaction Steps

To a solution of 3-(4-fluoro-benzoyl)-1,2,3,4,5,6,7,8,9,10-decahydro-azepino[4,5-b]indole-5-carboxylic acid ethyl ester (Example 6, 60 mg, 0.16 mmol) in DCM (2 mL) was added TEA (45 μL, 0.32 mmol) and a solution of tert-butyl hypochlorite (19.2 mL, 0.16 mmol) in DCM (1 mL) at 0° C. and the mixture was stirred for 0.5 h at 0° C. Cold water was added to quench the reaction mixture and the aqueous layer was separated and extracted with DCM. The combined organic layer was washed with water and dried over MgSO4. Evaporation of solvent gave a crude, which was purified by column chromatography on silica gel, eluting with MeOH-DCM (1:19) to give the title compound (6.5 mg) with some starting material (27 mg) recovered. 1H-NMR(CDCl3): δ 10.07 (1H, s), 7.57 (2H, m), 7.52 (1H, s), 7.10 (2H, m), 4.19 (2H, q), 4.07 (2H, t), 2.89 (2H, t), 2.62 (2H, t), 2.43 (2H, t), 1.80 (4H, m), 1.19 (3H, t). MS (ES): 383 (MH+).

Provenance & Evidence