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

HRID 509314노트

반응식

HRID 509314 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-c5de1539f0fa4e2780c2099c8bd46eaf
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09096527B2

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