Hydrochloric Acid → 4-(2-Chloro-6-methoxyphenyl)-6-(3-hydroxypropyl)-9-methoxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione

Participants

Reaction Steps

The reaction of 6-(3-{[tert-Butyl(dimethyl)silyl]oxy}propyl)-4-(2-chloro-6-methoxyphenyl)-9-methoxy-4,5,6,10c-tetrahydropyrrolo[3,4-c]carbazole-1,3(2H,3aH)-dione (IV; Ar=2-chloro-6-methoxyphenyl, R10═CH2CH2CH2OSiMe2t-Bu) (104) prepared as described in example 57 with DDQ using the procedure described in example 70 followed by reaction with 2N HCl in THF/methanol gave 4-(2-Chloro-6-methoxyphenyl)-6-(3-hydroxypropyl)-9-methoxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione (V; Ar=2-chloro-6-methoxyphenyl, R10═CH2CH2CH2OH) (105) in a 76% yield as an orange powder; mp 224–227° C. 1H NMR δ [(CD3)2SO] 11.05 (br, 1H), 8.51 (d, J=2.6 Hz, 1H), 7.75 (s, 1H), 7.69 (d, J=8.9 Hz, 1H), 7.44 (dd, J=8.2, 8.2 Hz, 1H), 7.31 (dd, J=8.9, 2.6 Hz, 1H), 7.18 (d, J=8.2 Hz, 1H), 7.13 (d, J=8.2 Hz, 1H), 4.63 (t, J=4.9 Hz, 1H), 4.51 (t, J=6.8 Hz, 2H), 3.91 (s, 3H), 3.68 (s, 3H), 3.41 (m, 2H), 1.89 (m, 2H). Found: C, 69.71; H, 4.53; N, 6.43. C25H22N2O5 requires C, 69.76; H, 5.15; N, 6.51.

Provenance & Evidence