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

HRID 42180

反応式

HRID 42180 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 312751,4-Dioxane溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-6b923c2f957b4a1c8a9cd3883d749232
出典データセット
uspto-grants-2013_09
特許番号
US08536168B2

関連ノート

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