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Cesium carbonate → 7-(2-oxopyrrolidin-1-yl)-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-one

HRID 1162897
ノート
印刷プレビュー

反応式

HRID 1162897 の反応式
I[C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[C:19]([F:22])([F:21])[F:20])[NH:8][C:9]2=[O:12])=[CH:4][CH:3]=1.CC1(C)C2C=CC=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=2OC2C1=CC=CC=2P(C1C=CC=CC=1)C1C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+].[NH:71]1[CH2:75][CH2:74][CH2:73][C:72]1=[O:76].[Cl-].[NH4+]>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]>[O:76]=[C:72]1[CH2:73][CH2:74][CH2:75][N:71]1[C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[C:19]([F:22])([F:21])[F:20])[NH:8][C:9]2=[O:12])=[CH:4][CH:3]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 5

HCID 10796Cesium carbonateHCID 120252-PyrrolidoneHCID 25517Ammonium ChlorideHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 231568037-iodo-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-one

生成物 1

HCID 11853673
7-(2-oxopyrrolidin-1-yl)-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-one
収率 82%

試薬・触媒・溶媒 1

HCID 9811564Bis(dibenzylideneacetone)palladium触媒

実験手順

The 7-iodo-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-one (20.8 mg, 0.05 mmol) prepared in step D of Example 1-1, tris(dibenzylideneacetone)dipalladium (2.2 mg, 0.0025 mmol), 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (4.2 mg, 0.0075 mmol), cesium carbonate (22.8 mg, 0.07 mmol), and 2-pyrrolidone (4.6 μl) were suspended in 1,4-dixane (0.5 ml), and the suspension was then stirred under heating to reflux overnight. Thereafter, the reaction solution was cooled to a room temperature, and a saturated ammonium chloride aqueous solution was then added thereto, followed by extraction with ethyl acetate. The extract was dried over anhydrous sodium sulfate, and the solvent was then distilled away under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate hexane=2:1 to 5:1), so as to obtain 7-(2-oxopyrrolidin-1-yl)-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-one (15.3 mg; yield: 82%) in the form of a colorless solid.

後処理

  1. temperatureunder heating
  2. temperatureto reflux overnight
  3. extractionfollowed by extraction with ethyl acetate
  4. dry with materialThe extract was dried over anhydrous sodium sulfate
  5. distillationthe solvent was then distilled away under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (ethyl acetate hexane=2:1 to 5:1)

出典と根拠

ORDレコード
ord-5e4bd257854b4b4ca93ef7ccfb179943
出典データセット
uspto-grants-2010_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07820693B2

反応ノート

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