Cesium carbonate → 2-Fluoro-3-(2-oxopyrrolidin-1-yl)-5-trifluoromethylbenzoic Acid Methyl Ester

HRID 1612443ノート

反応式

HRID 1612443 の反応式
[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[C:6](Br)[C:5]=1[F:15].C(=O)([O-])[O-].[Cs+].[Cs+].[NH:23]1[CH2:27][CH2:26][CH2:25][C:24]1=[O:28].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.COC(=O)C1C=C(C(F)(F)F)C=C(Cl)C=1N1CCCC1=O>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]>[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[C:6]([N:23]2[CH2:27][CH2:26][CH2:25][C:24]2=[O:28])[C:5]=1[F:15]

参加物

8

反応物 5

HCID 10796Cesium carbonateHCID 120252-PyrrolidoneHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 69361010Methyl 3-bromo-2-fluoro-5-(trifluoromethyl)benzoateHCID 695899223-Chloro-2-(2-oxopyrrolidin-1-yl)-5-trifluoromethylbenzoic acid methyl ester

生成物 1

HCID 695896852-Fluoro-3-(2-oxopyrrolidin-1-yl)-5-trifluoromethylbenzoic Acid Methyl Ester

試薬・触媒・溶媒 2

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

実験手順

3-Bromo-2-fluoro-5-trifluoromethylbenzoic acid methyl ester (500 mg, 1.95 mmol)), caesium carbonate (950 mg, 2.92 mmol), pyrrolidin-2-one (248 mg, 2.92 mmol), 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (68 mg, 0.117 mmol) and tris(dibenzylideneacetone)dipalladium (0) (36 mg, 0.039 mmol) were refluxed under argon in dioxane (7 ml) for 18 h. After cooling, the mixture was filtered and evaporated in vacuo. Column chromatography on silica gel eluting with a gradient of 20–50% ethyl acetate in hexane gave a mixture of D24 and 3-chloro-2-(2-oxopyrrolidin-1-yl)-5-trifluoromethylbenzoic acid methyl ester (195 mg).

後処理

  1. temperatureAfter cooling
  2. filtrationthe mixture was filtered
  3. customevaporated in vacuo
  4. customColumn chromatography on silica gel eluting with a gradient of 20–50% ethyl acetate in hexane gave

出典と根拠

ORDレコード
ord-1062ebf2599f40babd596cc640ecafcd
出典データセット
uspto-grants-2006_01
特許番号
US06992103B2

反応ノート

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