tert-Butylsulfinamide, (R)-(+)- → HCID 90301392, 화합물

HRID 627647노트

반응식

HRID 627647 반응식
[Br:1][C:2]1[CH:3]=[C:4]([C:9](=O)[CH3:10])[C:5]([F:8])=[N:6][CH:7]=1.[CH3:12][C:13]([S@:16]([NH2:18])=[O:17])([CH3:15])[CH3:14]>C1COCC1.[Cl-].[Na+].O.[O-]CC.[Ti+4].[O-]CC.[O-]CC.[O-]CC>[Br:1][C:2]1[CH:3]=[C:4](/[C:9](=[N:18]\[S@@:16]([C:13]([CH3:15])([CH3:14])[CH3:12])=[O:17])/[CH3:10])[C:5]([F:8])=[N:6][CH:7]=1

참가 물질

6

반응물 2

HCID 10964479tert-Butylsulfinamide, (R)-(+)-HCID 401519061-(5-Bromo-2-fluoropyridin-3-yl)ethan-1-one

생성물 1

HCID 90301392HCID 90301392, 화합물수율 99%

시약·촉매·용매 3

HCID 76524Titanium tetraethoxide촉매HCID 8028Tetrahydrofuran용매HCID 57417360Sodium chloride; water용매

실험 절차

A mixture of 1-(5-bromo-2-fluoropyridin-3-yl)ethanone (11 g, 51 mmol), (R)-2-methylpropane-2-sulfinamide (12.2 g, 101 mmol) and titanium (IV) ethoxide (26.1 mL, 126 mmol) in THF (100 mL) was heated to reflux for 2 h. The mixture was cooled to room temperature, brine was added and the mixture was stirred for 10 min. The suspension was filtered through silica gel. The organic phase was separated and the aqueous phase was extracted with EtOAc. The combined organic extracts were washed with brine, dried over Na2SO4, filtered, and concentrated. Purification by flash column chromatography on silica gel (eluted with 0-20% EtOAc/hexanes) gave (R,Z)—N-(1-(5-bromo-2-fluoropyridin-3-yl)ethylidene)-2-methylpropane-2-sulfinamide (16 g, 50 mmol, 99% yield) as a bright yellow oil. LC/MS (ESI) m/z=321 (M+H).

후처리

  1. temperaturewas heated
  2. temperatureto reflux for 2 h
  3. filtrationThe suspension was filtered through silica gel
  4. customThe organic phase was separated
  5. extractionthe aqueous phase was extracted with EtOAc
  6. washThe combined organic extracts were washed with brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customPurification by flash column chromatography on silica gel (eluted with 0-20% EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-6986b2dbdb43488c8b238cf07c34d92d
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09309263B2

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