(S)-tert-butyl 3-oxo-4-(pyridin-2-yl)butan-2-ylcarbamate → Tert-butyl 1-(6-fluoro-3,4-di(pyridin-2-yl)quinolin-2-yl)ethylcarbamate

HRID 1616061노트

반응식

HRID 1616061 반응식
O=[C:2]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1)[C@@H:3]([NH:5][C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9])[CH3:4].[NH2:20][C:21]1[CH:26]=[CH:25][C:24]([F:27])=[CH:23][C:22]=1[C:28]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][N:31]=1)=O>CC(O)C.O.O.[Na+].Cl[Au-](Cl)(Cl)Cl>[F:27][C:24]1[CH:23]=[C:22]2[C:21](=[CH:26][CH:25]=1)[N:20]=[C:2]([CH:3]([NH:5][C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9])[CH3:4])[C:13]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1)=[C:28]2[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][N:31]=1

참가 물질

5

반응물 2

HCID 58318617(S)-tert-butyl 3-oxo-4-(pyridin-2-yl)butan-2-ylcarbamateHCID 69673534(2-Amino-5-fluorophenyl)(pyridin-2-yl)methanone

생성물 1

HCID 67595333Tert-butyl 1-(6-fluoro-3,4-di(pyridin-2-yl)quinolin-2-yl)ethylcarbamate수율 58.9%

시약·촉매·용매 2

HCID 18949434Sodium tetrachloroaurate dihydrate촉매HCID 3776Isopropanol용매

실험 절차

A mixture of (S)-tert-butyl 3-oxo-4-(pyridin-2-yl)butan-2-ylcarbamate (0.427 g, 1.615 mmol), (2-amino-5-fluorophenyl)(pyridin-2-yl)methanone (0.384 g, 1.777 mmol), and sodium tetrachloroaurate(III) dihydrate (0.032 g, 0.081 mmol) in 2-propanol (9.50 mL) was heated under reflux. After 71 h, the mixture was cooled to rt and evaporated to dryness. The mixture was dissolved in DCM (50 mL) and washed with brine (1×50 mL), and dried over Na2SO4. The solution was filtered and concentrated in vacuo to give the crude material. The crude material was purified by silica gel column chromatography eluting with a gradient of 0% to 50% EtOAc in hexane, to provide tert-butyl 1-(6-fluoro-3,4-di(pyridin-2-yl)quinolin-2-yl)ethylcarbamate (0.423 g, 0.952 mmol, 58.9% yield) as orange syrupy solid: LC-MS (ESI) m/z 445.1 [M+H]+. The orange syrupy solid was used without further purification. Epimerization occurred during the condensation.

후처리

  1. temperaturewas heated
  2. temperatureunder reflux
  3. customevaporated to dryness
  4. dissolutionThe mixture was dissolved in DCM (50 mL)
  5. washwashed with brine (1×50 mL)
  6. dry with materialdried over Na2SO4
  7. filtrationThe solution was filtered
  8. concentrationconcentrated in vacuo
  9. customto give the crude material
  10. customThe crude material was purified by silica gel column chromatography
  11. washeluting with a gradient of 0% to 50% EtOAc in hexane

출처 및 근거

ORD 기록
ord-4e9f237989d0437ebe59229c1852881c
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08765768B2

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