3-(Trifluoromethyl)phenylboronic acid → HCID 23654203, compound

HRID 1785511Notes

Reaction equation

HRID 1785511 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]([F:36])([F:35])[C:26]1[CH:27]=[C:28](B(O)O)[CH:29]=[CH:30][CH:31]=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:30]4[CH:29]=[CH:28][CH:27]=[C:26]([C:25]([F:36])([F:35])[F:24])[CH:31]=4)[N:7]=3)[CH:11]=[N:12][C:13]=2[CH:18]=1

Participants

3

Reactant 2

HCID 27343883-(Trifluoromethyl)phenylboronic acidHCID 57595851HCID 57595851, compound

Product 1

HCID 23654203HCID 23654203, compoundYield 58.1%

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 3-trifluoromethylphenylboronic acid (28.5 mg, 0.15 mmol) gave 2-(5,6-Dimethoxy-benzoimidazol-1-yl)-4-(3-trifluoromethyl-phenyl)-thiazole-5-carboxylic acid (26.1 mg, 58%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 13.90 (br.s. 1H); 8.82 (s, 1 H); 8.37-8.47 (m, 2 H); 7.87 (s, 1 H); 7.82 (d, 1 H); 7.72 (t, 1 H); 7.39 (s, 1 H); 3.87 (s, 3 H); 3.85 (s, 3 H). MS 450 m/z (M+1).

Sources & evidence

ORD record
ord-d6bdc22d77c04d9da84b1af804deef63
Source dataset
uspto-grants-2009_03
Patent number
US07504513B2

Reaction notes

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