Water → HCID 67099972, compound

HRID 2077807Notes

Reaction equation

HRID 2077807 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-ab6f660ce2134ed784ea375938bb725c
Source dataset
uspto-grants-2011_04
Patent number
US07928119B2

Reaction notes

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