N,N'-Dimethylethylenediamine → 1-(6-Chloropyridin-3-YL)pyrrolidin-2-one

HRID 42180

반응식

HRID 42180 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](I)=[CH:4][N:3]=1.[NH:9]1[CH2:13][CH2:12][CH2:11][C:10]1=[O:14].C([O-])([O-])=O.[K+].[K+].CNCCNC>O1CCOCC1.[Cu]I>[Cl:1][C:2]1[N:3]=[CH:4][C:5]([N:9]2[CH2:13][CH2:12][CH2:11][C:10]2=[O:14])=[CH:6][CH:7]=1

참가 물질

7

반응물 4

HCID 8070N,N'-DimethylethylenediamineHCID 11430Potassium CarbonateHCID 120252-PyrrolidoneHCID 43971762-Chloro-5-iodopyridine

생성물 1

HCID 574716111-(6-Chloropyridin-3-YL)pyrrolidin-2-one수율 103%

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 312751,4-Dioxane용매

실험 절차

To a solution of 2-chloro-5-iodopyridine (200 mg, 0.84 mmol) in 4 mL anhydrous dioxane was added 2-pyrrolidinone (60.8 μL, 0.79 mmol), K2CO3 (415.6 mg, 3 mmol), CuI (15.9 mg, 0.084 mmol), and N,N′-dimethyl-1,2-ethanediamine (11.8 μL, 0.083 mmol) in a 2 dram screw-top vial. The vial is evacuated and flushed with nitrogen. The reaction mixture was heated to reflux for 18 h. The reaction mixture was filtered through celite and filtrate was concentrated to afford the crude material. The mixture was purified by flash chromatography on silica gel, eluting with 50-100% EtOAc:heptane. Fractions containing the desired products were combined and concentrated to afford the desired product as a white solid (160 mg, yield: 97.4%).

후처리

  1. customThe vial is evacuated
  2. customflushed with nitrogen
  3. temperatureThe reaction mixture was heated
  4. temperatureto reflux for 18 h
  5. filtrationThe reaction mixture was filtered through celite and filtrate
  6. concentrationwas concentrated
  7. customto afford the crude material
  8. customThe mixture was purified by flash chromatography on silica gel
  9. washeluting with 50-100% EtOAc
  10. additionFractions containing the desired products
  11. concentrationconcentrated

출처 및 근거

ORD 기록
ord-6b923c2f957b4a1c8a9cd3883d749232
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08536168B2

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