Sodium hydride → HCID 66868939, compound

HRID 250738Notes

Reaction equation

HRID 250738 reaction equation
[H-].[Na+].[C:3]1([C:9]2[NH:10][CH:11]=[CH:12][N:13]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH2:14]([NH:18][C:19]1[CH:24]=[C:23](F)[CH:22]=[CH:21][C:20]=1[N+:26]([O-:28])=[O:27])[CH:15]([CH3:17])[CH3:16]>CN(C)C=O.C(OCC)(=O)C>[CH2:14]([NH:18][C:19]1[CH:24]=[C:23]([N:13]2[CH:12]=[CH:11][N:10]=[C:9]2[C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:22]=[CH:21][C:20]=1[N+:26]([O-:28])=[O:27])[CH:15]([CH3:17])[CH3:16]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 695912-PhenylimidazoleHCID 62376587HCID 62376587, compound

Product 1

HCID 66868939HCID 66868939, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Add sodium hydride (60% oil dispersion, 94 mg, 2.36 mmol) to a solution of 2-phenylimidazole (340 mg, 2.36 mmol) in 8 mL dimethylformamide. Stir at room temperature for 15 minutes and then add N-[isobutyl]2-nitro-5-fluoroaniline (500 mg, 2.36 mmol). Stir at 60° C. over night under a nitrogen atmosphere. Dilute the reaction mixture with ethyl acetate and wash with dilute aqueous sodium bicarbonate. Dry the organic phase over sodium sulfate, filter, and concentrate under reduced pressure. Subject the residue to radial silica gel chromatography, eluting with a gradient of 0.1%-5% methanol in dichloromethane to provide the desired compound as a yellow solid (450 mg, 57%).

Workup

  1. stirringStir at 60° C. over night under a nitrogen atmosphere
  2. washwash with dilute aqueous sodium bicarbonate
  3. dry with materialDry the organic phase over sodium sulfate
  4. filtrationfilter
  5. concentrationconcentrate under reduced pressure
  6. washeluting with a gradient of 0.1%-5% methanol in dichloromethane

Sources & evidence

ORD record
ord-50001655f0634ead8c74792c71a73812
Source dataset
uspto-grants-2011_01
Patent number
US07863310B2

Reaction notes

Loading…