(2,6-Dimethoxyphenyl)boronic acid → 4-(2,6-dimethoxyphenyl)-9-hydroxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione

HRID 11022Notes

Reaction equation

HRID 11022 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.[CH3:21][O:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([O:29][CH3:30])[C:24]=1B(O)O>>[CH3:21][O:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([O:29][CH3:30])[C:24]=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 2734343(2,6-Dimethoxyphenyl)boronic acidHCID 118428349-hydroxy-4-iodopyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione

Product 1

HCID 104753624-(2,6-dimethoxyphenyl)-9-hydroxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dioneYield 43%

Procedure

The reaction of 9-hydroxy-4-iodopyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione, prepared as in example 7, with 2,6-dimethoxybenzeneboronic acid according to the procedure described in example 8 gave 4-(2,6-dimethoxyphenyl)-9-hydroxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione (19) (I, Ar=2,6-dimethoxyphenyl) in a 43% yield; mp 275–277° C. (dec). 1H NMR δ [(CD3)2SO] 11.62 (br s, 1H), 10.83 (br s, 1H), 9.21 (br s, 1H), 8.29 (d, J=2.4 Hz, 1H), 7.42 (s, 1H), 7.41 (d, J=8.4 Hz, 1H), 7.35 (t, J=8.4 Hz, 1H), 7.04 (dd, J=8.4, 2.4 Hz, 1H), 6.75 (d, J=8.4 Hz, 2H), 3.63 (s, 6H). Found: C, 66.31; H, 4.50, N, 6.70. C22H16N2O5,1/2H2O requires C, 66.49; H, 4.31; N, 7.04.

Sources & evidence

ORD record
ord-85df1732c626402a8b775bd55215bcb2
Source dataset
uspto-grants-2006_08
Patent number
US07094798B1

Reaction notes

Loading…