3,5-Dichlorophenylboronic acid → HCID 23654117, compound

HRID 1785509Notes

Reaction equation

HRID 1785509 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].[Cl:24][C:25]1[CH:26]=[C:27](B(O)O)[CH:28]=[C:29]([Cl:31])[CH:30]=1>>[Cl:24][C:25]1[CH:26]=[C:27]([C:6]2[N:7]=[C:8]([N:10]3[C:14]4[CH:15]=[C:16]([O:21][CH3:22])[C:17]([O:19][CH3:20])=[CH:18][C:13]=4[N:12]=[CH:11]3)[S:9][C:5]=2[C:3]([OH:2])=[O:4])[CH:28]=[C:29]([Cl:31])[CH:30]=1

Participants

3

Reactant 2

HCID 27343313,5-Dichlorophenylboronic acidHCID 57595851HCID 57595851, compound

Product 1

HCID 23654117HCID 23654117, compoundYield 51.1%

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 3,5-dichlorophenylboronic acid (27 mg, 0.15 mmol) gave 4-(3,5-Dichloro-phenyl)-2-(5,6-dimethoxy-benzoimidazol-1-yl)-thiazole-5-carboxylic acid (23 mg, 51%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.84 (s, 1 H); 8.15 (s, 2 H); 7.83 (s, 1 H); 7.73 (s, 1 H); 7.39 (s, 1 H); 3.89 (s, 3 H); 3.85 (s, 3 H). MS 450 m/z (M+1).

Sources & evidence

ORD record
ord-e933b33566be4a8490467ce7b6bfd579
Source dataset
uspto-grants-2009_03
Patent number
US07504513B2

Reaction notes

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