Boron tribromide → 4-(2-Chlorophenyl)-6-{3-[(3R,5S)-3,5-dimethylpiperazinyl]-3-oxopropyl}-9-hydroxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione

Participants

Reaction Steps

Demethylation of (126) prepared as described in example 239 (with BBr3 using the procedure described in example 80 except that the reaction time was 48 h gave (127) as a yellow powder (38%), mp 220–224° C. (dec). 1H NMR δ [(CD3)2SO] 11.07 (br s, 1H) 9.36 (br s, 1H), 8.72 (br, 1H), 8.34 br, 1H), 7.72 (s, 0.5H), 7.71 (s, 0.5H), 7.60–7.54 (m, 2H), 7.52–7.43 (m, 3H), 7.13 (dd, J=8.8, 2.4 Hz, 1H), 4.68 (m, 3H), 4.15, 4.12 (2s, 2H), 2.94 (m, 1H), 2.72 (m, 1H), 2.19 (m, 1H), 2.00 (m, 1H), 1.84 (m, 1H), 0.86, 0.84 (2d, J=5.8 Hz, 3H), 0.64 (2d, J=6.1 Hz, 3H). Found: C, 63.38; H, 5.38; N, 9.96. C29H17ClN4O4.H2O requires C, 63.44; H, 5.32; N, 10.20.

Provenance & Evidence