Proton sponge → 6-Methoxy-8-(phenylsulfonyl)-1,3,4,8-tetrahydro-2H-[1,4]oxazepino[6,7-e]indole

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Reaction Steps

To 6-methoxy-2-methyl-8-(phenylsulfonyl)-1,3,4,8-tetrahydro-2H-[1,4]oxazepino[6,7-e]indole (Example 48, 0.030 g, 0.081 mmol), 1,8-Bis(dimethylamino)-naphthalene (0.010 g, 0.048 mmol) and 1-chloroethyl chloroformate (25 mg, 0.18 mmol) were added followed by dry DCM (2 mL). The reaction mixture was stirred at room temperature for 30 minutes. The solvent was removed under reduced pressure and the crude material was dissolved in dry MeOH (3 mL). The reaction mixture was heated at reflux for 2 hours, cooled and the crude product was purified by preparative HPLC (XTerra C18, 50 mM NH4HCO3 pH 10-CH3CN) to give the title compound (3 mg). MS m/z 359 [M+H]+.

Provenance & Evidence