Methyl morpholine oxide → 4-(3-Bromo-4,5-dimethoxyphenyl)-7-methyl-pyrrolo[2,3-h]chroman-2-one

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Reaction Steps

To a mixture of 4-(3-bromo-4,5-dimethoxyphenyl)-2-hydroxy-7-methyl-pyrrolo[2,3-h]chroman (6 mg; 0.014 mmol), molecular sieves 4A° (20 mg) and 4-methylmorpholin-N-oxide (2 mg; 0.017 mmol ) in dichloromethane (0.5 ml) at 0° C. was added TPAP (0.4 mg). The mixture was stirred at this temperature for 0.5 h and at room temperature for 20 min. It was concentrated and passed through a bond-elute (hexane:ethyl acetate=9:1 and 4:1 as eluents), yielding the title compound (1.2 mg; 20%). 1H NMR (acetone-d6): 7.30 (d, J=3.1 Hz; 1H), 7.21 (dd, J=0.8, 8.4 Hz; 1H), 7.03 (d, J=2.0 Hz; 1H), 6.92 (d, J=8.4 Hz; 1H), 6.87 (dd, J=0.6, 2.1 Hz; 1H), 6.55 (dd, J=0.8, 3.1 Hz; 1H), 4.55 (t, J=5.9 Hz; 1H), 3.86, 3.84, 3.77 (s each, 9H), 3.24 (dd, J=6.4, 15.8 Hz; 1H), 3.13 (dd, J=5.9, 15.8 Hz; 1H).

Provenance & Evidence