Sodium hydride → HCID 15435340, compound

HRID 618727Notes

Reaction equation

HRID 618727 reaction equation
[O:1]([C:8]1[CH:13]=[CH:12][C:11]([C:14]2[NH:15][C:16]([C:26]3[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=3)=[C:17]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=3)[N:18]=2)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[C:34](=O)([O:40]C(C)(C)C)[O:35][C:36]([CH3:39])([CH3:38])[CH3:37]>CN(C=O)C>[C:36]([O:35][C:34]([N:18]1[C:17]([C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=2)=[C:16]([C:26]2[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=2)[N:15]=[C:14]1[C:11]1[CH:10]=[CH:9][C:8]([O:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:13][CH:12]=1)=[O:40])([CH3:39])([CH3:38])[CH3:37]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 10219638Carbonic acid, bis(1,1-dimethylethyl) esterHCID 21847958HCID 21847958, compound

Product 1

HCID 15435340HCID 15435340, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(4-phenoxyphenyl)-4-(4-fluorophenyl)-5-(4-pyridyl)imidazole (prepared by the method described in Example 2; 150 mg, 0.37 mmol) in DMF (1 mL) was added solid sodium hydride (8.9 mg of a 60% oil dispersion, 0.37 mmol). The reaction was stirred for 1 h at room temperature and then cooled to -20° C. Di-t-butyl carbonate (85 μL, 0.37 mmol) was added and the reaction was placed in a refrigerator for 4 days. The reaction was quenched by the addition of water and the mixture was extracted with ethyl acetate (3 times). The combined extracts were successively washed with water (2 times) and saturated salt solution and dried over anhydrous sodium sulfate. The solution was filtered and the solvent removed by rotoevaporation. The residue was purified by flash column chromatography on silica gel eluted with 0-1.5% methanol in methylene chloride to yield the title compound, mass spectrum (CI) m/e=508 (M+1)+.

Workup

  1. temperaturecooled to -20° C
  2. waitthe reaction was placed in a refrigerator for 4 days
  3. customThe reaction was quenched by the addition of water
  4. extractionthe mixture was extracted with ethyl acetate (3 times)
  5. washThe combined extracts were successively washed with water (2 times) and saturated salt solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationThe solution was filtered
  8. customthe solvent removed by rotoevaporation
  9. customThe residue was purified by flash column chromatography on silica gel
  10. washeluted with 0-1.5% methanol in methylene chloride

Sources & evidence

ORD record
ord-e948f99d67b6451f9f875d42ebc9b297
Source dataset
uspto-grants-1999_09
Patent number
US05955480

Reaction notes

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