Water → HCID 67099972, compound

HRID 858537Notes

Reaction equation

HRID 858537 reaction equation
[Cl:1][C:2]1[C:3]([C:40]([F:43])([F:42])[F:41])=[CH:4][C:5]2[N:9]=[C:8]([CH:10]([OH:12])[CH3:11])[N:7]([C:13]3[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][O:21][Si:22]([C:35]([CH3:38])([CH3:37])[CH3:36])([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)=[CH:15][CH:14]=3)[C:6]=2[CH:39]=1.[H-].[Na+].[CH3:46]I.O>CN(C=O)C>[Cl:1][C:2]1[C:3]([C:40]([F:43])([F:41])[F:42])=[CH:4][C:5]2[N:9]=[C:8]([CH:10]([O:12][CH3:46])[CH3:11])[N:7]([C:13]3[CH:14]=[CH:15][C:16]([CH2:19][CH2:20][O:21][Si:22]([C:35]([CH3:36])([CH3:38])[CH3:37])([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[C:29]4[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=4)=[CH:17][CH:18]=3)[C:6]=2[CH:39]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 67099737HCID 67099737, compound

Product 1

HCID 67099972HCID 67099972, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1-[6-chloro-1-[4-(2-{[(1,1-dimethylethyl)(diphenyl)silyl]oxy}ethyl)phenyl]-5-(trifluoromethyl)-1H-benzimidazol-2-yl]ethanol (step 4, 590 mg, 0.95 mmol) in DMF (10 ml) was added NaH (45 mg, 1.13 mmol). Then the mixture was added MeI (0.08 ml, 1.23 mmol) at room temperature. The mixture was stirred at room temperature for 1 h. The mixture was added water (30 ml) and extracted with ethyl acetate (100 ml). The organic layer was washed with water (50 ml), brine (50 ml), then dried (Na2SO4). After removal of solvent, the crude product was purified by flash column chromatography eluting with hexane/ethyl acetate (3:1) to afford 550 mg (91%) of the title compound as colorless oil.

Workup

  1. extractionextracted with ethyl acetate (100 ml)
  2. washThe organic layer was washed with water (50 ml), brine (50 ml)
  3. dry with materialdried (Na2SO4)
  4. customAfter removal of solvent
  5. customthe crude product was purified by flash column chromatography
  6. washeluting with hexane/ethyl acetate (3:1)

Sources & evidence

ORD record
ord-d92199683c9241bbb1f99abc71ae8203
Source dataset
uspto-grants-2006_12
Patent number
US07148234B2

Reaction notes

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