2-Thiopheneboronic acid → HCID 10065463, compound

HRID 11030Notes

Reaction equation

HRID 11030 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.[S:21]1[CH:25]=[CH:24][CH:23]=[C:22]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:22]4[S:21][CH:25]=[CH:24][CH:23]=4)[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 27339602-Thiopheneboronic acidHCID 118428349-hydroxy-4-iodopyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione

Product 1

HCID 10065463HCID 10065463, compoundYield 69%

Procedure

The reaction of 9-hydroxy-4-iodopyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione prepared as in example 7 with 2-thiopheneboronic acid according to the procedure described in example 8 gave 9-hydroxy-4-(2-thienyl)pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione (505) (1; Ar=2-thienyl) in a 69% yield; mp (THF/CH2Cl2/hexane) 179–184° C. (dec). 1H NMR [(CD3)2SO] δ 11.75 (br s, 1H), 11.11 (br s, 1H), 9.26 (br s, 1H), 8.34 (d, J=2.4 Hz, 1H), 7.75 (s, 1H), 7.73 (dd, J=3.6, 1.0 Hz, 1H), 7.68 (dd, J=5.1, 1.3 Hz, 1H), 7.43 (d, J=8.7 Hz, 1H), 7.20 (dd, J=5.1, 3.6 Hz, 1H), 7.07 (dd, J=8.7, 2.5 Hz, 1H). Found: C, 62.38; H, 3.11; N, 7.74. C18H10N2O3S.3/4H2O requires C, 62.15; H, 3.33; N, 8.05.

Sources & evidence

ORD record
ord-afa00cd55c8c4518af21430b59e7bcd7
Source dataset
uspto-grants-2006_08
Patent number
US07094798B1

Reaction notes

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