Cesium carbonate → HCID 66877664, 화합물

HRID 1015768노트

반응식

HRID 1015768 반응식
Br[C:2]1[CH:9]=[CH:8][C:7]([Cl:10])=[CH:6][C:3]=1[C:4]#[N:5].[NH:11]1[CH2:15][CH2:14][CH2:13][C:12]1=[O:16].C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Cl:10][C:7]1[CH:8]=[CH:9][C:2]([N:11]2[CH2:15][CH2:14][CH2:13][C:12]2=[O:16])=[C:3]([CH:6]=1)[C:4]#[N:5]

참가 물질

6

반응물 3

HCID 10796Cesium carbonateHCID 120252-PyrrolidoneHCID 103309442-Bromo-5-chlorobenzonitrile

생성물 1

HCID 66877664HCID 66877664, 화합물

시약·촉매·용매 2

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 312751,4-Dioxane용매

실험 절차

(Step 1) To a solution (139 ml) of 2-bromo-5-chlorobenzonitrile (15.0 g), pyrrolidin-2-one (7.90 ml) and cesium carbonate (45.2 g) in 1,4-dioxane were added tris(dibenzylideneacetone)dipalladium (1.59 g) and 4,5-bis(biphenylphosphino)-9,9-dimethylxanthine (2.0 g) at room temperature under a nitrogen atmosphere, and the mixture was heated under reflux for 3 hr. The mixture was allowed to cool to room temperature, and extracted with ethyl acetate and water. The organic layer was filtered through celite, and washed with ethyl acetate. The filtrate was dried over sodium sulfate, and filtered. The solvent was evaporated under reduced pressure. The obtained residue was purified by column chromatography (ethyl acetate:hexane=1:10→1:1) to give 5-chloro-2-(2-oxopyrrolidin-1-yl)benzonitrile (12.5 g) as yellow crystals.

후처리

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 3 hr
  3. extractionextracted with ethyl acetate and water
  4. filtrationThe organic layer was filtered through celite
  5. washwashed with ethyl acetate
  6. dry with materialThe filtrate was dried over sodium sulfate
  7. filtrationfiltered
  8. customThe solvent was evaporated under reduced pressure
  9. customThe obtained residue was purified by column chromatography (ethyl acetate:hexane=1:10→1:1)

출처 및 근거

ORD 기록
ord-48829f5ada1640ff9881b4000624126b
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07985862B2

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