(2H-1,3-benzodioxol-5-yl)boronic acid → 4-Benzo[1,3]dioxol-5-yl-2-(5,6-dimethoxy-benzoimidazol-1-yl)-thiazole-5-carboxylic acid

HRID 1785495Notes

Reaction equation

HRID 1785495 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].[CH2:24]1[O:32][C:31]2[CH:30]=[CH:29][C:28](B(O)O)=[CH:27][C:26]=2[O:25]1>>[O:25]1[C:26]2[CH:27]=[CH:28][C:29]([C:6]3[N:7]=[C:8]([N:10]4[C:14]5[CH:15]=[C:16]([O:21][CH3:22])[C:17]([O:19][CH3:20])=[CH:18][C:13]=5[N:12]=[CH:11]4)[S:9][C:5]=3[C:3]([OH:2])=[O:4])=[CH:30][C:31]=2[O:32][CH2:24]1

Participants

3

Reactant 2

HCID 2734371(2H-1,3-benzodioxol-5-yl)boronic acidHCID 57595851HCID 57595851, compound

Product 1

HCID 236539154-Benzo[1,3]dioxol-5-yl-2-(5,6-dimethoxy-benzoimidazol-1-yl)-thiazole-5-carboxylic acidYield 25%

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 3,4-methylenedioxybenzeneboronic acid (24.9 mg, 0.15 mmol) gave 4-Benzo[1,3]dioxol-5-yl-2-(5,6-dimethoxy-benzoimidazol-1-yl)-thiazole-5-carboxylic acid (10.5 mg, 25%) as a white solid. MS m/z 426 (M+1).

Sources & evidence

ORD record
ord-1ab497d711da436ea193882c249cc4ab
Source dataset
uspto-grants-2009_03
Patent number
US07504513B2

Reaction notes

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