Boron tribromide → HCID 21980394, compound

Participants

Reaction Steps

The reaction of 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) prepared as described in example 53 with BBr3 using the procedure described in example 80 gave 9-Hydroxy-4-(2-hydroxyphenyl)-6-(3-hydroxypropyl)pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione (VI; Ar=2-hydroxyphenyl, R10═CH2CH2CH2OH) (101) in an 82% yield as an orange powder, mp 306–309° C. 1H NMR δ [(CD3)2SO] 10.90 (br, 1H), 9.40 (br, 1H), 8.38 (d, J=2.4 Hz, 1H), 7.67 (s, 1H), 7.56 (d, J=8.8 Hz, 1H), 7.30–7.23 (m, 2H), 7.13 (dd, J=8.8, 2.4 Hz, 1H), 6.94–6.88 (m, 2H), 4.78 (br, 2H), 4.47 (t, J=6.8 Hz, 2H), 3.41 (t, J=6.0 Hz, 2H), 1.91 (m, 2H). Found: C, 66.85; H, 4.61; N, 6.63. C23H18N2O5.1/2H2O requires C, 67.14; H, 4.65; N, 6.80.

Provenance & Evidence