Boron tribromide → 4-(2-Chloro-6-methoxyphenyl)-9-hydroxy-6-(2-hydroxyethyl)pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione

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Reaction Steps

The reaction of 4-(2-Chloro-6-methoxyphenyl)-6-(2-hydroxyethyl)-9-methoxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione (V; Ar=2-chloro-6-methoxyphenyl, R10═CH2CH2OH) (111) prepared as described in example 63 with BBr3 using the procedure described in example 80 except that the reaction conditions were 2 h at 0° C. gave 4-(2-Chloro-6-methoxyphenyl)-9-hydroxy-6-(2-hydroxyethyl)pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione (VI; Ar-2-chloro-6-methoxyphenyl, R10═CH2CH2OH) (112) in a 56% yield as a yellow powder (56%); mp 275–278° C. 1H NMR δ [(CD3)2SO] 10.98 (br s, 1H). 9.30 (br s, 1H), 8.36 (d, J=2.4 Hz, 1H), 7.70 (s, 1H), 7.57 (d, J=8.7 Hz, 1H), 7.43 (dd, J=8.3, 8.3 Hz, 1H), 7.17 (d, J=7.9 Hz, 1H), 7.14–7.09 (m, 2H), 4.81 (t, J=5.5 Hz, 1H), 4.46 (t, J=5.3 Hz, 2H), 3.74 (dt, J=5.5, 5.3 Hz, 2H), 3.66 (s, 3H). FABMS found [M+H]+: 439.0882, 437.0889. C23H18ClNO5 requires 439.0875, 437.0904.

Provenance & Evidence