1-Methyl-1H-indole-5-boronic acid → HCID 23654294, compound

HRID 1785513Notes

Reaction equation

HRID 1785513 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][N:25]1[C:33]2[C:28](=[CH:29][C:30](B(O)O)=[CH:31][CH:32]=2)[CH:27]=[CH:26]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]=[C:28]5[C:33](=[CH:32][CH:31]=4)[N:25]([CH3:24])[CH:26]=[CH:27]5)[N:7]=3)[CH:11]=[N:12][C:13]=2[CH:18]=1

Participants

3

Reactant 2

HCID 27598671-Methyl-1H-indole-5-boronic acidHCID 57595851HCID 57595851, compound

Product 1

HCID 23654294HCID 23654294, compoundYield 12%

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 N-methylindole-5-boronic acid (26.2 mg, 0.15 mmol) gave 2-(5,6-Dimethoxy-benzoimidazol-1-yl)-4-(1-methyl-1H-indol-5-yl)-thiazole-5-carboxylic acid (5.1 mg, 12%) as a white solid. MS 435 m/z (M+1).

Sources & evidence

ORD record
ord-ce2172ac60ee41dc908fb5a9b301b45b
Source dataset
uspto-grants-2009_03
Patent number
US07504513B2

Reaction notes

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