Iodine → (S)-N-((S)-(4-methoxyphenyl)(3-(trifluoromethyl)pyridin-2-yl)methyl)-2-methylpropane-2-sulfinamide

HRID 2370753Notes

Reaction equation

HRID 2370753 reaction equation
[Mg].II.Br[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][CH:6]=1.[CH3:13][C:14]([S@@:17](/[N:19]=[CH:20]/[C:21]1[C:26]([C:27]([F:30])([F:29])[F:28])=[CH:25][CH:24]=[CH:23][N:22]=1)=[O:18])([CH3:16])[CH3:15]>C1COCC1>[CH3:12][O:11][C:8]1[CH:9]=[CH:10][C:5]([C@@H:20]([C:21]2[C:26]([C:27]([F:28])([F:30])[F:29])=[CH:25][CH:24]=[CH:23][N:22]=2)[NH:19][S@:17]([C:14]([CH3:16])([CH3:15])[CH3:13])=[O:18])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 807IodineHCID 77304-BromoanisoleHCID 5462224MagnesiumHCID 89310312(NE,S)-2-methyl-N-[[3-(trifluoromethyl)pyridin-2-yl]methylidene]propane-2-sulfinamide

Product 1

HCID 71143955(S)-N-((S)-(4-methoxyphenyl)(3-(trifluoromethyl)pyridin-2-yl)methyl)-2-methylpropane-2-sulfinamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Magnesium metal (0.095 g, 3.91 mmol) was activated using a crystal of iodine prior to addition of THF (1 mL). 1-Bromo-4-methoxybenzene (0.400 g, 2.139 mmol) was added, and the reaction was left without stirring for 5 minutes after which initiation was observed. Additional THF (15 mL) was added and the mixture was stirred for 2 hours. (S,E)-2-Methyl-N-((3-(trifluoromethyl)pyridin-2-yl)methylene)propane-2-sulfinamide (0.500 g, 1.797 mmol) was added, and the mixture was stirred for 10 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 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 (S)—N—((S)-(4-methoxyphenyl)-(3-(trifluoromethyl)pyridin-2-yl)methyl)-2-methylpropane-2-sulfinamide.

Workup

  1. waitthe reaction was left
  2. stirringthe mixture was stirred for 2 hours
  3. stirringthe mixture was stirred for 10 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 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-7fc5e4ee1ed34b13917e0f2785132410
Source dataset
uspto-grants-2014_04
Patent number
US08710043B2

Reaction notes

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