Imidazole → 1-{2-[2-Methyl-3-(4-trifluoromethyl-phenyl)-benzo[b]thiophen-6-yloxy]-ethyl}-1H-imidazole

HRID 270485Notes

Reaction equation

HRID 270485 reaction equation
[CH3:1][C:2]1[S:6][C:5]2[CH:7]=[C:8]([O:11][CH2:12][CH2:13]OS(C)(=O)=O)[CH:9]=[CH:10][C:4]=2[C:3]=1[C:19]1[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][CH:20]=1.[NH:29]1[CH:33]=[CH:32][N:31]=[CH:30]1.[H-].[Na+]>CN(C)C=O>[CH3:1][C:2]1[S:6][C:5]2[CH:7]=[C:8]([O:11][CH2:12][CH2:13][N:29]3[CH:33]=[CH:32][N:31]=[CH:30]3)[CH:9]=[CH:10][C:4]=2[C:3]=1[C:19]1[CH:24]=[CH:23][C:22]([C:25]([F:27])([F:26])[F:28])=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 24758Sodium hydrideHCID 86585430Methanesulfonic acid 2-[2-methyl-3-(4-trifluoromethyl-phenyl)-benzo[b]thiophen-6-yloxy]-ethyl ester

Product 1

HCID 223139841-{2-[2-Methyl-3-(4-trifluoromethyl-phenyl)-benzo[b]thiophen-6-yloxy]-ethyl}-1H-imidazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In analogy to the procedure described in example 53.1, Methanesulfonic acid 2-[2-methyl-3-(4-trifluoromethyl-phenyl)-benzo[b]thiophen-6-yloxy]-ethyl ester (example 49.2) was reacted with imidazole and sodium hydride in N,N-dimethylformamide at room temperature to yield 1-{2-[2-Methyl-3-(4-trifluoromethyl-phenyl)-benzo[b]thiophen-6-yloxy]-ethyl}-1H-imidazole as colorless oil, MS: 403 (MH+).

Sources & evidence

ORD record
ord-e5eaba38c5a744c39bf088ec972dccc5
Source dataset
uspto-grants-2008_11
Patent number
US07449483B2

Reaction notes

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