Sodium hydride → HCID 18463689, compound

HRID 2231106Notes

Reaction equation

HRID 2231106 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[NH:14][C:13]([C:15]([F:18])([F:17])[F:16])=[N:12][C:11]=2[C:19]2[CH:24]=[CH:23][C:22]([S:25]([CH3:28])(=[O:27])=[O:26])=[CH:21][CH:20]=2)=[CH:6][CH:5]=1.[CH3:29][Si:30]([CH2:33][CH2:34][O:35][CH2:36]Cl)([CH3:32])[CH3:31].[NH4+].[Cl-]>CN(C)C=O.CCCCCC>[F:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:14]([CH2:36][O:35][CH2:34][CH2:33][Si:30]([CH3:32])([CH3:31])[CH3:29])[C:13]([C:15]([F:18])([F:16])[F:17])=[N:12][C:11]=2[C:19]2[CH:24]=[CH:23][C:22]([S:25]([CH3:28])(=[O:26])=[O:27])=[CH:21][CH:20]=2)=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 9843038HCID 9843038, compound

Product 1

HCID 18463689HCID 18463689, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of hexane-washed sodium hydride (NaH) (110 mg of 60%, 2.8 mmol) in dimethylformamide (DMF) (15 ml) was stirred under a nitrogen atmosphere at 25° C. and a solution of 5-(4-fluorophenyl)-4-(4-methylsulfonylphenyl)-2-trifluoromethyl-1H-imidazole (Example 1) (970 mg, 2.5 mmol) in DMF (5 ml) was added over 15 minutes. This mixture was stirred an additional 30 minutes. Trimethylsilylethoxymethyl chloride (450 mg, 3 mmol) was added and the reaction mixture was stirred for 16 hours at 25° C. The reaction mixture was poured into 2% aqueous NH4Cl (150 ml) and extracted with ethyl acetate. After drying (Na2SO4) and solvent removal, the protected sulfone imidazole (1.1 g, 95%) was essentially pure and was used without further purification.

Workup

  1. stirringThis mixture was stirred an additional 30 minutes
  2. stirringthe reaction mixture was stirred for 16 hours at 25° C
  3. extractionextracted with ethyl acetate
  4. customAfter drying
  5. custom(Na2SO4) and solvent removal
  6. customwas used without further purification

Sources & evidence

ORD record
ord-44bcfe14aa5b48f9a42cdb934315a11e
Source dataset
uspto-grants-2002_07
Patent number
US06426360B1

Reaction notes

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