N-(1-(5-bromo-2-fluorophenyl)-3-(tert-butyldimethylsilyloxy)-2,2-difluoropropylidene)-2-methylpropane-2-sulfinamide → N-(2-(5-bromo-2-fluorophenyl)-4-(tert-butyldimethylsilyloxy)-3,3-difluorobutan-2-yl)-2-methylpropane-2-sulfinamide

HRID 81605Notes

Reaction equation

HRID 81605 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:28])=[C:6]([C:8](=[N:21][S:22]([C:24]([CH3:27])([CH3:26])[CH3:25])=[O:23])[C:9]([F:20])([F:19])[CH2:10][O:11][Si:12]([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13])[CH:7]=1.[CH3:29][Mg+].[Br-]>C(OCC)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:28])=[C:6]([C:8]([NH:21][S:22]([C:24]([CH3:27])([CH3:26])[CH3:25])=[O:23])([C:9]([F:20])([F:19])[CH2:10][O:11][Si:12]([C:15]([CH3:18])([CH3:16])[CH3:17])([CH3:14])[CH3:13])[CH3:29])[CH:7]=1

Participants

4

Reactant 2

HCID 86650272N-(1-(5-bromo-2-fluorophenyl)-3-(tert-butyldimethylsilyloxy)-2,2-difluoropropylidene)-2-methylpropane-2-sulfinamideHCID 178418689HCID 178418689, compound

Product 1

HCID 66666208N-(2-(5-bromo-2-fluorophenyl)-4-(tert-butyldimethylsilyloxy)-3,3-difluorobutan-2-yl)-2-methylpropane-2-sulfinamide

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
-35 °C

Procedure

To a solution of N-(1-(5-bromo-2-fluorophenyl)-3-(tert-butyldimethylsilyloxy)-2,2-difluoropropylidene)-2-methylpropane-2-sulfinamide (12 g, 24.04 mmol) in diethyl ether (120 mL) was added CH3MgBr (3M in Diethyl ether) (41 mL, 120 mmol) at −25° C. The reaction mixture was brought to 0° C. and maintained for 30 min. Reaction mixture was again cooled to −35° C. and quenched by drop wise addition of saturated ammonium chloride solution. Organic layer was separated and washed with brine and dried over anhydrous sodium sulphate. Crude compound was purified by column chromatography on silica gel with 8% ethyl acetate in Hexane to furnish title compound as a colorless liquid. Yield=8.8 g (71%). TLC (20% ethyl acetate in Hexane): Rf=0.33),

Workup

  1. customwas brought to 0° C.
  2. temperaturemaintained for 30 min
  3. customReaction mixture
  4. customquenched by drop wise addition of saturated ammonium chloride solution
  5. customOrganic layer was separated
  6. washwashed with brine
  7. dry with materialdried over anhydrous sodium sulphate
  8. customCrude compound was purified by column chromatography on silica gel with 8% ethyl acetate in Hexane

Sources & evidence

ORD record
ord-60f2275ae8994930968d402ca9e5a12d
Source dataset
uspto-grants-2014_09
Patent number
US08846658B2

Reaction notes

Loading…