tert-Butylsulfonamide → N-(1-(5-bromo-2-fluorophenyl)-3-(tert-butyldimethylsilyloxy)-2,2-difluoropropylidene)-2-methylpropane-2-sulfinamide

HRID 81604노트

반응식

HRID 81604 반응식
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:22])=[C:6]([C:8](=O)[C:9]([F:20])([F:19])[CH2:10][O:11][Si:12]([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13])[CH:7]=1.[CH3:23][C:24]([S:27]([NH2:30])(=O)=[O:28])([CH3:26])[CH3:25]>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:22])=[C:6]([C:8](=[N:30][S:27]([C:24]([CH3:26])([CH3:25])[CH3:23])=[O:28])[C:9]([F:20])([F:19])[CH2:10][O:11][Si:12]([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13])[CH:7]=1

참가 물질

4

반응물 2

HCID 2757335tert-ButylsulfonamideHCID 666657711-(5-Bromo-2-fluorophenyl)-3-(tert-butyldimethylsilyloxy)-2,2-difluoropropan-1-one

생성물 1

HCID 86650272N-(1-(5-bromo-2-fluorophenyl)-3-(tert-butyldimethylsilyloxy)-2,2-difluoropropylidene)-2-methylpropane-2-sulfinamide

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 1-(5-bromo-2-fluorophenyl)-3-(tert-butyldimethylsilyloxy)-2,2-difluoropropan-1-one (16.0 g, 40.4 mmol) in dry THF (350 mL) was added Ti(OEt)4 (16.7 mL, 80.4 mmol) and 2-Methyl-2-propane sulfonamide (5.8 g, 48.4 mmol) and refluxed for 16 h. Reaction mixture was concentrated under reduced pressure and the crude residue was directly purified by column chromatography on silica gel with 3% ethyl acetate in Hexane to furnish title compound as a colorless liquid. Yield=13.1 g (65.5%). TLC (10% ethyl acetate in Hexane): Rf=0.2),

후처리

  1. temperaturerefluxed for 16 h
  2. customReaction mixture
  3. concentrationwas concentrated under reduced pressure
  4. customthe crude residue was directly purified by column chromatography on silica gel with 3% ethyl acetate in Hexane

출처 및 근거

ORD 기록
ord-a5c164f675b84171bf5069ed12daae18
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846658B2

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