2,3-Dichlorobenzeneboronic acid → 4-(2,3-dichlorophenyl)-9-hydroxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione

HRID 11021Notes

Reaction equation

HRID 11021 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.[Cl:21][C:22]1[C:27]([Cl:28])=[CH:26][CH:25]=[CH:24][C:23]=1B(O)O>>[Cl:21][C:22]1[C:27]([Cl:28])=[CH:26][CH:25]=[CH:24][C:23]=1[C:8]1[C:7]2[C:16](=[O:20])[NH:17][C:18](=[O:19])[C:6]=2[C:5]2[C:4]3[CH:3]=[C:2]([OH:1])[CH:14]=[CH:13][C:12]=3[NH:11][C:10]=2[CH:9]=1

Participants

3

Reactant 2

HCID 27346612,3-Dichlorobenzeneboronic acidHCID 118428349-hydroxy-4-iodopyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione

Product 1

HCID 103186164-(2,3-dichlorophenyl)-9-hydroxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dioneYield 27%

Procedure

The reaction of 9-hydroxy-4-iodopyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione, prepared as in example 7, with 2,3-dichlorobenzeneboronic acid according to the procedure described in example 8 gave 4-(2,3-dichlorophenyl)-9-hydroxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione (18) (I, Ar=2,3-dichlorophenyl) in a yield 27%; mp 233–235° C. 1H NMR δ [(CD3)2SO] 11.87 (br, 1H), 11.05 (br, 1H), 9.29 (br, 1H), 8.31 (d, J=2.5 Hz, 1H), 7.74–7.70 (m, 1H), 7.55 (s, 1H), 7.48–7.45 (m, 3H), 7.09 (dd, J=8.7, 2.5 Hz, 1H). Found: C, 59.19; H, 3.04; N, 6.56, C20H10Cl2N2O3.1/2H2O requires C, 59.13; H, 2.73; N, 6.89.

Sources & evidence

ORD record
ord-23f300f9fcb1453a9803c071809cca00
Source dataset
uspto-grants-2006_08
Patent number
US07094798B1

Reaction notes

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