Reaction equation
[Mg].Br[C:3]1[CH:4]=[CH:5][C:6]2[CH:10]=[CH:9][S:8][C:7]=2[CH:11]=1.[CH3:12][Si:13]([CH3:30])([CH3:29])[CH2:14][CH2:15][O:16][CH2:17][N:18]1[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=2[N:20]=[C:19]1[CH:27]=[O:28].Cl>O1CCCC1>[S:8]1[CH:9]=[CH:10][C:6]2[CH:5]=[CH:4][C:3]([CH:27]([C:19]3[N:18]([CH2:17][O:16][CH2:15][CH2:14][Si:13]([CH3:29])([CH3:30])[CH3:12])[C:22]4[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=4[N:20]=3)[OH:28])=[CH:11][C:7]1=2Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To a suspension of magnesium (86 mg) in tetrahydrofuran is added a solution of 6-bromobenzo[b]thiophene (which can be prepared according to WO2006/107784) (500 mg) in tetrahydrofuran. After reflux for 3 h, a solution of 1-(2-trimethylsilylethoxymethyl)-1H-benzimidazole-2-carbaldehyde (which can be prepared according to US2003/220341 or US6476041 for example) (635 mg) in tetrahydrofuran is added to the Grignard reagent at room temperature. After stirring for 12 h, the reaction mixture is treated with diluted hydrochloric acid and the organic phase is dried over magnesium sulfate and concentrated under reduced pressure. The residue is purified by chromatography over silica gel (gradient dichloromethane/methanol from 100/0 to 90/10) to afford benzo[b]thiophen-6-yl[1-(2-trimethylsilylethoxymethyl)-1H-benzimidazol-2-yl]methanol.
Workup
- temperatureAfter reflux for 3 h
- dry with materialthe organic phase is dried over magnesium sulfate
- concentrationconcentrated under reduced pressure
- customThe residue is purified by chromatography over silica gel (gradient dichloromethane/methanol from 100/0 to 90/10)
Sources & evidence
- ORD record
- ord-63fbbe7b5c3d418383d3f1adabb00085
- Source dataset
- uspto-grants-2014_08
- Patent number
- US08802664B2
Linked notes
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