2-(Trifluoromethyl)benzeneboronic acid → 9-Hydroxy-4-(2-trifluoromethylphenyl)pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione

HRID 11025Notes

Reaction equation

HRID 11025 reaction equation
[OH:1][C:2]1[CH:14]=[CH:13][C:12]2[NH:11][C:10]3[CH:9]=[C:8](I)[C:7]4[C:16](=[O:20])[NH:17][C:18](=[O:19])[C:6]=4[C:5]=3[C:4]=2[CH:3]=1.[F:21][C:22]([F:33])([F:32])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1B(O)O>>[OH:1][C:2]1[CH:14]=[CH:13][C:12]2[NH:11][C:10]3[CH:9]=[C:8]([C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=4[C:22]([F:33])([F:32])[F:21])[C:7]4[C:16](=[O:20])[NH:17][C:18](=[O:19])[C:6]=4[C:5]=3[C:4]=2[CH:3]=1

Participants

3

Reactant 2

HCID 27343872-(Trifluoromethyl)benzeneboronic acidHCID 118428349-hydroxy-4-iodopyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione

Product 1

HCID 118446099-Hydroxy-4-(2-trifluoromethylphenyl)pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dioneYield 47%

Procedure

The reaction of 9-hydroxy-4-iodopyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione, prepared as in example 7, with 2-trifluoromethylbenzeneboronic acid according to the procedure described in example 8 gave 9-Hydroxy-4-(2-trifluoromethylphenyl)pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione (22) (I, Ar=2-trifluoromethylphenyl) in a 47% yield, mp 210° C. (dec). 1H NMR δ [(CD3)2SO] 11.81 (br s, 1H), 11.01 (br s, 1H), 9.30 (br s, 1H), 8.31 (d, J=2.4 Hz, 1H), 7.86 (br d, J=7.2 Hz, 1H), 7.75–7.64 (m, 2H), 7.51 (s, 1H), 7.49 (br d, J=7.6 Hz, 1H), 7.46 (d, J=8.7 Hz, 1H), 7.09 (dd, J=8.7, 2.4 Hz, 1H). EIMS found M+: 396.0721. C21H11F3N2O3 requires 396.0722.

Sources & evidence

ORD record
ord-28d9d76d2d9f4954aa1e97b069f520f3
Source dataset
uspto-grants-2006_08
Patent number
US07094798B1

Reaction notes

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