Water → HCID 67099737, compound

HRID 724186Notes

Reaction equation

HRID 724186 reaction equation
[Cl:1][C:2]1[C:3]([C:23]([F:26])([F:25])[F:24])=[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][OH:21])=[CH:15][CH:14]=3)[C:6]=2[CH:22]=1.[Si:27](Cl)([C:40]([CH3:43])([CH3:42])[CH3:41])([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C(N(CC)CC)C.O>ClCCl>[Cl:1][C:2]1[C:3]([C:23]([F:24])([F:26])[F:25])=[CH:4][C:5]2[N:9]=[C:8]([CH:10]([OH:12])[CH3:11])[N:7]([C:13]3[CH:14]=[CH:15][C:16]([CH2:19][CH2:20][O:21][Si:27]([C:40]([CH3:43])([CH3:42])[CH3:41])([C:34]4[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=4)[C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)=[CH:17][CH:18]=3)[C:6]=2[CH:22]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 94078tert-ButyldiphenylchlorosilaneHCID 21875790HCID 21875790, compound

Product 1

HCID 67099737HCID 67099737, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 1-[6-chloro-1-[4-(2-hydroxyethyl)phenyl]-5-(trifluoromethyl)-1H-benzimidazol-2-yl]ethanol (step 3, 461 mg, 1.19 mmol), tert-Butyldiphenylsilyl chloride (0.35 ml, 1.3 mmol), triethylamine (0.2 ml, 1.4 mmol) and N,N-dimethylaminopyridine (6 mg, 0.05 mmol) in dichloromethane (11 ml) was stirred under nitrogen at room temperature for 4 h. was added water (50 ml) and extracted with dichloromethane (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 (3:1/1:1) to afford 590 mg (80%) of the title compound as white amorphous.

Workup

  1. extractionextracted with dichloromethane (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 (3:1/1:1)

Sources & evidence

ORD record
ord-d074659ae25649e5930ec9e9b122efba
Source dataset
uspto-grants-2006_11
Patent number
US07141580B2

Reaction notes

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