Boron tribromide → 3-(4-(2-Chlorophenyl)-9-hydroxy-1,3-dioxo-2,3-dihydropyrrolo[3,4-c]carbazol-6(1H)-yl)-N-[2-(1H-imidazol-5-yl)ethyl]propanamide

Participants

Reaction Steps

Demethylation of (128) prepared as described in example 241 with BBr3 using the procedure described in example 80 except that the reaction time was 48 h gave (129) as a yellow powder (46%), mp 158–162° C. (dec). 1H NMR δ [(CD3)2SO] 11.75 (br, 1H), 11.05 (br s, 1H), 9.36 (br s, 1H), 8.37 (d, J=2.4 Hz, 1H), 7.91 (t, J=5.3 Hz, 1H), 7.71 (s, 1H), 7.59–7.54 (m, 2H), 7.50–7.42 (m, 4H), 7.14 (dd, J=8.8, 2.4 Hz, 1H), 6.57 (br, 1H), 4.65 (t, J=6.5 Hz, 2H), 3.13 (m, 2H), 2.55 (t, J=6.5 Hz, 1H), 2.40 (t, J=6.5 Hz, 1H). FABMS found [M+H]+: 530.1431, 528.1440. C28H23ClN5O4 requires 530.1409, 528.1439.

Provenance & Evidence