Iodine → HCID 67157927, compound

Participants

Reaction Steps

A solution of 6-benzyloxy-5-methoxyindole (1.90 g, prepared according to procedure described by Benigni, J. D. and Minnis, R. L., J. Heterocycl. Chem. 1965, 2, 387 and Sinhababu, A. K. and Borchardt, R. T., J. Org. Chem. 1983, 48, 3347) in dry dimethylformamide (37.5 mL) was treated with ground potassium hydroxide (1.24 g) and a solution of iodine (1.96 g) in dry dimethylformamide (37.5 mL) dropwise at room temperature. The reaction mixture was stirred at room temperature for 2 hours, then treated with 4-dimethylaminopyridine (69 mg) followed by a solution of di-tert-butyldicarbonate (2.05 g) in dry dimethylformamide and stirring was continued for a further 1 hour. The reaction mixture was poured into aqueous sodium sulfite solution (0.2%). The aqueous phase was extracted three times with ethyl acetate (100 mL). The combined organic phases were washed with water (100 mL), then with brine (100 mL), then dried over magnesium sulfate and then evaporated. The residue was subjected to flash column chromatography on silica eluting with a mixture of cyclohexane and ethyl acetate (1:9, v/v) to give the title compound (3.35 g) as a white solid. TLC: RF=0.58 (dichloromethane). MS: EI (70 eV); m/z=479 M+ (45%); 423 (100%); 332 (75%).

Provenance & Evidence