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

HRID 1612443노트

반응식

HRID 1612443 반응식
[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]

참가 물질

8

반응물 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

생성물 1

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

시약·촉매·용매 2

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

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-1062ebf2599f40babd596cc640ecafcd
출처 데이터셋
uspto-grants-2006_01
특허 번호
US06992103B2

반응 노트

불러오는 중…