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

HRID 509316Notes

Reaction equation

HRID 509316 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-1602ca8a8daa4b449f551a26005e57c3
Source dataset
uspto-grants-2015_08
Patent number
US09096527B2

Reaction notes

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