Hydrochloric Acid → 6-(3-Hydroxypropyl)-9-methoxy-4-(2-methoxyphenyl)pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione

Participants

Reaction Steps

The reaction of 6-(3-{[tert-Butyl(dimethyl)silyl)oxy}propyl)-9-methoxy-4-(2-methoxyphenyl)-4,5,6,10c-tetrahydropyrrolo[3,4-c]carbazole-1,3(2H,3aH)-dione (IV; Ar=2-methoxyphenyl; R10═CH2CH2CH2OSiMe2t-Bu) prepared as described in example 52 with DDQ using the procedure described in example 70 followed reaction with 2N HCl in THF/methanol gave 6-(3-Hydroxypropyl)-9-methoxy-4-(2-methoxyphenyl)pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione (V; Ar=2-methoxyphenyl, R10═CH2CH2CH2OH) (100) in a 72% yield as an orange powder; mp 223–225° C. 1H NMR δ [(CD3)2SO] 10.99 (br s, 1H), 8.53 (d, 2.6 Hz, 1H), 7.74 (s, 1H), 7.67 (d, J=8.9 Hz, 1H), 7.45–7.40 (m, 1H), 7.36 (dd, J=7.4, 1.7 Hz, 1H), 7.29 (dd, J=8.9, 2.7 Hz, 1H), 7.11 (d, J=8.1 Hz, 1H), 7.06 (dd, J=7.2, 7.2 Hz, 1H), 4.63 (t, J=4.8 Hz, 1H), 4.52 (t, J=6.9 Hz, 2H), 3.90 (s, 3H), 3.69 (s, 3H), 3.40 (m, 2H), 1.91 (m, 2H). Found: C, 69.55; H, 5.31; N, 6.30. C25H22N2O5 requires C69.76; H, 5.15; N, 6.51.

Provenance & Evidence