Cesium carbonate → HCID 66877664、化合物

HRID 1014022ノート

反応式

HRID 1014022 の反応式
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]

参加物

6

反応物 3

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

生成物 1

HCID 66877664HCID 66877664、化合物

試薬・触媒・溶媒 2

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 312751,4-Dioxane溶媒

実験手順

(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.

後処理

  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)

出典と根拠

ORDレコード
ord-5f8ea70c80444bd4b8b73e148e21b1d1
出典データセット
uspto-grants-2011_07
特許番号
US07982044B2

反応ノート

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