Pyridine → 2-Acetoxy-4-(3-bromo-4,5-dimethoxyphenyl)-7-methyl-pyrrolo[2,3-h]chroman

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-(3-bromo-4,5-dimethoxyphenyl)-2-hydroxy-7-methyl-pyrrolo[2,3-h]chroman (37 mg, 0.089 mmol) in dichloromethane (0.5 ml) at 0° C. was added pyridine (0.010 ml, 0.133 mmol), 4-dimethylaminopyridine (1.0 mg, 0.0082 mmol) and acetic anhydride (0.010 ml, 0.111 mmol) and the resulting solution was stirred at 0° C. for 0.5 h. The solution was then stirred at room temperature for 1.5 h. The reaction mixture was diluted with dichloromethane and the organic solution was extracted with water and a saturated aqueous solution of sodium bicarbonate. The organic layer was dried and concentrated in vacuo. The residue was purified by flash chromatography (20% ethyl acetate/hexane) to give 39 mg (90%) of the title compound. 1H NMR (CD3CN): 7.10 (dd, 1H); 7.02 (m, 1H); 6.94-6.84 (m, 2H); 6.72-6.60 (m, 1H); 6.53 (m, 1H); 6.43 (m, 1H); 4.38-4.19 (m, 1H); 3.80-3.74 (m, 9H); 2.56-2.40 (m, 1H); 2.32 (m, 1H); 1.96 (s, 3H).

Provenance & Evidence