4-Vinylphenylboronic acid → HCID 23654289, compound

HRID 1785518Notes

Reaction equation

HRID 1785518 reaction equation
C[O:2][C:3]([C:5]1[S:9][C:8]([N:10]2[C:14]3[CH:15]=[C:16]([O:21][CH3:22])[C:17]([O:19][CH3:20])=[CH:18][C:13]=3[N:12]=[CH:11]2)=[N:7][C:6]=1Br)=[O:4].B(O)(O)[C:25]1[CH:30]=[CH:29][C:28]([CH:31]=[CH2:32])=[CH:27][CH:26]=1>>[CH3:20][O:19][C:17]1[C:16]([O:21][CH3:22])=[CH:15][C:14]2[N:10]([C:8]3[S:9][C:5]([C:3]([OH:2])=[O:4])=[C:6]([C:25]4[CH:30]=[CH:29][C:28]([CH:31]=[CH2:32])=[CH:27][CH:26]=4)[N:7]=3)[CH:11]=[N:12][C:13]=2[CH:18]=1

Participants

3

Reactant 2

HCID 27343934-Vinylphenylboronic acidHCID 57595851HCID 57595851, compound

Product 1

HCID 23654289HCID 23654289, compoundYield 37.3%

Procedure

In a similar manner as described for Example 26, 4-bromo-2-(5,6-dimethoxy-benzoimidazol-1-yl)-thiazole-5-carboxylic acid methyl ester (40 mg, 0.1 mmol) and 4-vinylboronic acid (22.2 mg, 0.15 mmol) gave 2-(5,6-Dimethoxy-benzoimidazol-1-yl)-4-(4-vinyl-phenyl)-thiazole-5-carboxylic acid (15.2 mg, 37%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 13.69 (br.s., 1 H); 8.82 (s, 1 H); 7.95 (d, 2 H); 7.84 (s, 1 H); 7.60 (d, 2H); 7.39 (s, 1H); 6.82 (dd, 1 H); 5.97 (dd, 1 H); 5.37 (dd, 1 H); 3.86 (s, 3 H); 3.86 (s, 3 H). MS 408 m/z (M+1).

Sources & evidence

ORD record
ord-2601f61c18774ab7a121314b7e5cdd18
Source dataset
uspto-grants-2009_03
Patent number
US07504513B2

Reaction notes

Loading…