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

HRID 216412Notes

Reaction equation

HRID 216412 reaction equation
[CH3:1][Mg]Br.[CH3:4][C:5]([CH3:36])([CH3:35])[CH2:6][C:7]1[N:8]=[C:9]([C:18](=[O:34])[CH:19]([F:33])[C:20]2[CH:25]=[CH:24][C:23]([C:26]3[CH:31]=[CH:30][C:29]([F:32])=[CH:28][N:27]=3)=[CH:22][CH:21]=2)[N:10]([S:12]([N:15]([CH3:17])[CH3:16])(=[O:14])=[O:13])[CH:11]=1>O1CCCC1>[CH3:4][C:5]([CH3:36])([CH3:35])[CH2:6][C:7]1[N:8]=[C:9]([C:18]([OH:34])([CH3:1])[CH:19]([F:33])[C:20]2[CH:25]=[CH:24][C:23]([C:26]3[CH:31]=[CH:30][C:29]([F:32])=[CH:28][N:27]=3)=[CH:22][CH:21]=2)[N:10]([S:12]([N:15]([CH3:16])[CH3:17])(=[O:14])=[O:13])[CH:11]=1

Participants

4

Reactant 2

HCID 866385164-(2,2-dimethylpropyl)-2-{fluoro[4-(5-fluoropyridin-2-yl)phenyl]acetyl}-N,N-dimethyl-1H-imidazole-1-sulfonamideHCID 178418573HCID 178418573, compound

Product 1

HCID 686684984-(2,2-dimethylpropyl)-2-{2-fluoro-2-[4-(5-fluoropyridin-2-yl)phenyl]-1-hydroxy-1-methylethyl}-N,N-dimethyl-1H-imidazole-1-sulfonamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methylmagnesium bromide (3 M in diethyl ether) (ca. 15 μL, 0.04 mmol) was added to a 0° C. solution of 4-(2,2-dimethylpropyl)-2-{fluoro[4-(5-fluoropyridin-2-yl)phenyl]acetyl}-N,N-dimethyl-1H-imidazole-1-sulfonamide (10 mg, 0.02 mmol) in tetrahydrofuran (3 mL). After warming slowly to ambient temperature, the reaction was quenched with a few drops of water and concentrated in vacuo. Chromatography over silica eluting with 0-50% ethyl acetate/hexane afforded 4-(2,2-dimethylpropyl)-2-{2-fluoro-2-[4-(5-fluoropyridin-2-yl)phenyl]-1-hydroxy-1-methylethyl}-N,N-dimethyl-1H-imidazole-1-sulfonamide.

Workup

  1. customthe reaction was quenched with a few drops of water
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-190d93f74f7543669310ffcd9a707fff
Source dataset
uspto-grants-2012_06
Patent number
US08193228B2

Reaction notes

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