Hydrochloric Acid → 8-(Phenylsulfonyl)-1,3,4,8-tetrahydro-2H-[1,4]oxazepino[6,7-e]indole

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Reaction Conditions

Reaction Steps

1-Chloroethyl chloroformate (1.0 mL, 7.0 mmol) was added to a solution of 2-methyl-8-(phenylsulfonyl)-1,3,4,8-tetrahydro-2H-[1,4]oxazepino[6,7-e]indole (Example 5, 0.15 g, 0.44 mmol), and 1,8-bis-(dimethylamino)-naphthalene (proton sponge) (0.056 g, 0.26 mmol) in DCM (10 mL) and the mixture was stirred at 43° C. for 1 hour. 1.0 M HCl in diethylether (2.5 mL, 2.5 mmol) was added and the mixture was evaporated. The residue was dissolved in dry MeOH (10 mL) and heated at 78° C. for 30 minutes and evaporated. The residue was dissolved in DCM and washed with water, brine, and the organic phase was dried (MgSO4) and evaporated. The crude product was purified by flash chromatography on silica gel using MeOH:DCM:NEt3 (5:94:1) as the eluent to give the title compound (11 mg) as a light pink solid. MS m/z 329 [M+H]+.

Provenance & Evidence