(2,3-Difluorophenyl)boronic acid → HCID 23654017, compound

HRID 1785501Notes

Reaction equation

HRID 1785501 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].[F:24][C:25]1[C:30]([F:31])=[CH:29][CH:28]=[CH:27][C:26]=1B(O)O>>[F:24][C:25]1[C:30]([F:31])=[CH:29][CH:28]=[CH:27][C:26]=1[C:6]1[N:7]=[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)[S:9][C:5]=1[C:3]([OH:2])=[O:4]

Participants

3

Reactant 2

HCID 2734333(2,3-Difluorophenyl)boronic acidHCID 57595851HCID 57595851, compound

Product 1

HCID 23654017HCID 23654017, compoundYield 39%

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 2,3-difluorophenylboronic acid (23.7 mg, 0.15 mmol) gave 4-(2,3-Difluoro-phenyl)-2-(5,6-dimethoxy-benzoimidazol-1-yl)-thiazole-5-carboxylic acid (16.2 39%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 13.81 (br.s., 1 H); 8.83 (s, 1 H); 7.74 (s, 1 H); 7.52-7.64 (m, 2 H); 7.40 (s, 1 H); 7.33-7.39 (m, 1 H); 3.85 (s, 3 H); 3.83 (s, 3 H). MS m/z 418 (M+1).

Sources & evidence

ORD record
ord-bd991cebe8ea4376aafae9d62ce28f18
Source dataset
uspto-grants-2009_03
Patent number
US07504513B2

Reaction notes

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