2,3-Dichlorobenzeneboronic acid → 4-(2,3-dichlorophenyl)-9-hydroxypyrrolo[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 2,3-dichlorobenzeneboronic acid according to the procedure described in example 8 gave 4-(2,3-dichlorophenyl)-9-hydroxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione (18) (I, Ar=2,3-dichlorophenyl) in a yield 27%; mp 233–235° C. 1H NMR δ [(CD3)2SO] 11.87 (br, 1H), 11.05 (br, 1H), 9.29 (br, 1H), 8.31 (d, J=2.5 Hz, 1H), 7.74–7.70 (m, 1H), 7.55 (s, 1H), 7.48–7.45 (m, 3H), 7.09 (dd, J=8.7, 2.5 Hz, 1H). Found: C, 59.19; H, 3.04; N, 6.56, C20H10Cl2N2O3.1/2H2O requires C, 59.13; H, 2.73; N, 6.89.

Provenance & Evidence