2-Methylphenyl boronic acid → HCID 23654015, compound

HRID 1785500Notes

Reaction equation

HRID 1785500 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].[CH3:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1B(O)O>>[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:26]4[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=4[CH3:24])[N:7]=3)[CH:11]=[N:12][C:13]=2[CH:18]=1

Participants

3

Reactant 2

HCID 27332672-Methylphenyl boronic acidHCID 57595851HCID 57595851, compound

Product 1

HCID 23654015HCID 23654015, compoundYield 57%

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-methylphenylboronic acid (20.4 mg, 0.15 mmol) gave 2-(5,6-Dimethoxy-benzoimidazol-1-yl)-4-o-tolyl-thiazole-5-carboxylic acid (22.5 mg, 57%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 13.43 (br.s., 1 H); 8.82 (s, 1 H); 7.68 (s, 1 H); 7.41 (d, 1 H); 7.40 (s, 1 H); 7.31-7.39 (m, 2 H); 7.27 (td, 1 H); 3.85 (s, 3 H); 3.81 (s, 3 H); 2.29 (s, 3 H). MS m/z 396 (M+1).

Sources & evidence

ORD record
ord-235ff213f38548958d27e1579ebdf497
Source dataset
uspto-grants-2009_03
Patent number
US07504513B2

Reaction notes

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