Hydrochloric Acid → benzo[b]thiophen-6-yl[1-(2-trimethylsilylethoxymethyl)-1H-benzimidazol-2-yl]methanol

HRID 572899

Reaction equation

HRID 572899 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=2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 5462224MagnesiumHCID 120171281-(2-Trimethylsilylethoxymethyl)-2-formyl-benzimidazoleHCID 127444006-Bromo-benzo[b]thiophene

Product 1

HCID 66835918benzo[b]thiophen-6-yl[1-(2-trimethylsilylethoxymethyl)-1H-benzimidazol-2-yl]methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

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 U.S. Pat. No. 6,476,041 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

  1. temperatureAfter reflux for 3 h
  2. dry with materialthe organic phase is dried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue is purified by chromatography over silica gel (gradient dichloromethane/methanol from 100/0 to 90/10)

Sources & evidence

ORD record
ord-12eeb77a7f3e448580fd926482aeb6c5
Source dataset
uspto-grants-2015_05
Patent number
US09029357B2

Linked notes

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