2-(Trifluoromethyl)benzeneboronic acid → 9-Hydroxy-4-(2-trifluoromethylphenyl)pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione

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Reaction Steps

The reaction of 9-hydroxy-4-iodopyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione, prepared as in example 7, with 2-trifluoromethylbenzeneboronic acid according to the procedure described in example 8 gave 9-Hydroxy-4-(2-trifluoromethylphenyl)pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione (22) (I, Ar=2-trifluoromethylphenyl) in a 47% yield, mp 210° C. (dec). 1H NMR δ [(CD3)2SO] 11.81 (br s, 1H), 11.01 (br s, 1H), 9.30 (br s, 1H), 8.31 (d, J=2.4 Hz, 1H), 7.86 (br d, J=7.2 Hz, 1H), 7.75–7.64 (m, 2H), 7.51 (s, 1H), 7.49 (br d, J=7.6 Hz, 1H), 7.46 (d, J=8.7 Hz, 1H), 7.09 (dd, J=8.7, 2.4 Hz, 1H). EIMS found M+: 396.0721. C21H11F3N2O3 requires 396.0722.

Provenance & Evidence