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

HRID 1622554Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1622554
[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

Komponenten

6

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

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 resulting mixture was stirred for 2 hours. Next, (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 were mixed and separated. The organic layer was dried with magnesium sulfate 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.

Aufarbeitung

  1. waitthe reaction was left
  2. stirringthe resulting 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 were mixed
  7. customseparated
  8. dry with materialThe organic layer was dried with magnesium sulfate
  9. customevaporated to dryness under reduced pressure
  10. customPurification

Quellen und Nachweise

ORD-Eintrag
ord-5ed0fed17c6145f59a64afee3a38e652
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08778941B2

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