4-(2,2-dimethylpropyl)-2-{1-[4-(5-fluoropyridin-2-yl)benzyl]vinyl}-N,N-dimethyl-1H-imidazole-1-sulfonamide → 4-(2,2-dimethylpropyl)-2-{2-[4-(5-fluoropyridin-2-yl)phenyl]-1-methylethyl}-N,N-dimethyl-1H-imidazole-1-sulfonamide

HRID 425431Notes

Reaction equation

HRID 425431 reaction equation
[CH3:1][C:2]([CH3:32])([CH3:31])[CH2:3][C:4]1[N:5]=[C:6]([C:15]([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]3[CH:29]=[CH:28][C:27]([F:30])=[CH:26][N:25]=3)=[CH:20][CH:19]=2)=[CH2:16])[N:7]([S:9]([N:12]([CH3:14])[CH3:13])(=[O:11])=[O:10])[CH:8]=1>CO.[OH-].[OH-].[Pd+2]>[CH3:1][C:2]([CH3:31])([CH3:32])[CH2:3][C:4]1[N:5]=[C:6]([CH:15]([CH3:16])[CH2:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]3[CH:29]=[CH:28][C:27]([F:30])=[CH:26][N:25]=3)=[CH:20][CH:19]=2)[N:7]([S:9]([N:12]([CH3:14])[CH3:13])(=[O:10])=[O:11])[CH:8]=1

Participants

4

Reactant 1

HCID 667058444-(2,2-dimethylpropyl)-2-{1-[4-(5-fluoropyridin-2-yl)benzyl]vinyl}-N,N-dimethyl-1H-imidazole-1-sulfonamide

Product 1

HCID 667056824-(2,2-dimethylpropyl)-2-{2-[4-(5-fluoropyridin-2-yl)phenyl]-1-methylethyl}-N,N-dimethyl-1H-imidazole-1-sulfonamide

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

Pd(OH)2 (5 mg) was added to a solution of 4-(2,2-dimethylpropyl)-2-{1-[4-(5-fluoropyridin-2-yl)benzyl]vinyl}-N,N-dimethyl-1H-imidazole-1-sulfonamide in methanol. After stirring under an atmosphere of hydrogen (balloon) at ambient temperature for 1 h, the reaction mixture was filtered through a silica plug (rinsing with ethyl acetate) and concentrated in vacuo. Purification of the resulting crude product by silica preparatory plate chromatography eluting with 40% ethyl acetate/hexanes afforded 4-(2,2-dimethylpropyl)-2-{2-[4-(5-fluoropyridin-2-yl)phenyl]-1-methylethyl}-N,N-dimethyl-1H-imidazole-1-sulfonamide.

Workup

  1. filtrationthe reaction mixture was filtered through a silica plug (rinsing with ethyl acetate)
  2. concentrationconcentrated in vacuo
  3. customPurification of the resulting crude product by silica preparatory plate chromatography
  4. washeluting with 40% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-b149480905d74cceb5e50af2ede21a68
Source dataset
uspto-grants-2012_01
Patent number
US08106070B2

Reaction notes

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