Lithium Chloride → (S)-N-((S)-(3-fluoropyridin-2-yl)(4-(trifluoromethoxy)phenyl)methyl)-2-methylpropane-2-sulfinamide

HRID 2370755Notes

Reaction equation

HRID 2370755 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]([F:12])([F:11])[F:10])=[CH:4][CH:3]=1.C([Mg]Cl)(C)C.[Cl-].[Li+].[F:20][C:21]1[C:22](/[CH:27]=[N:28]/[S@:29]([C:31]([CH3:34])([CH3:33])[CH3:32])=[O:30])=[N:23][CH:24]=[CH:25][CH:26]=1>C1COCC1>[F:20][C:21]1[C:22]([C@H:27]([C:2]2[CH:7]=[CH:6][C:5]([O:8][C:9]([F:12])([F:11])[F:10])=[CH:4][CH:3]=2)[NH:28][S@:29]([C:31]([CH3:34])([CH3:33])[CH3:32])=[O:30])=[N:23][CH:24]=[CH:25][CH:26]=1

Participants

6

Reactant 4

HCID 433294Lithium ChlorideHCID 27772941-Iodo-4-(trifluoromethoxy)benzeneHCID 89310556(NE,S)-N-[(3-fluoro-2-pyridinyl)methylidene]-2-methylpropane-2-sulfinamideHCID 178418918HCID 178418918, compound

Product 1

HCID 71144126(S)-N-((S)-(3-fluoropyridin-2-yl)(4-(trifluoromethoxy)phenyl)methyl)-2-methylpropane-2-sulfinamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

1-Iodo-4-(trifluoromethoxy)benzene (1.00 g, 3.47 mmol) was dissolved in dry THF (10 mL) and cooled in an ice bath. Isopropylmagnesium chloride, lithium chloride complex (14% solution in THF, Aldrich, 3.07 mL, 2.82 mmol) was added, and the mixture was stirred for 10 min. A solution of (S,E)-N-((3-fluoropyridin-2-yl)methylene)-2-methylpropane-2-sulfinamide (0.643 g, 2.82 mmol) in dry THF (10 mL) was added and the reaction was stirred. After 50 minutes, the reaction was quenched by addition of saturated aqueous NH4Cl (10 mL). H2O (100 mL) and EtOAc (150 mL) were added, and the phases were mixed and separated. The organic layer was dried with MgSO4 and evaporated to dryness under reduced pressure. Purification using silica chromatography (hexane to EtOAc gradient) gave the desired (S)—N—((S)-(3-fluoropyridin-2-yl)(4-(trifluoro-methoxy)phenyl)methyl)-2-methylpropane-2-sulfinamide.

Workup

  1. temperaturecooled in an ice bath
  2. stirringthe reaction was stirred
  3. waitAfter 50 minutes
  4. customthe reaction was quenched by addition of saturated aqueous NH4Cl (10 mL)
  5. additionH2O (100 mL) and EtOAc (150 mL) were added
  6. additionthe phases were mixed
  7. customseparated
  8. dry with materialThe organic layer was dried with MgSO4
  9. customevaporated to dryness under reduced pressure
  10. customPurification

Sources & evidence

ORD record
ord-9ca6e92c36f94e1d84e606f5b801b956
Source dataset
uspto-grants-2014_04
Patent number
US08710043B2

Reaction notes

Loading…