Cesium carbonate → Methyl 3-[methyl(methylsulfonyl)amino]-5-(2-oxo-4-phenylpyrrolidin-1-yl)benzoate

HRID 1160454

반응식

HRID 1160454 반응식
Br[C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([N:12]([CH3:17])[S:13]([CH3:16])(=[O:15])=[O:14])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[C:18]1([CH:24]2[CH2:28][NH:27][C:26](=[O:29])[CH2:25]2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(=O)([O-])[O-].[Cs+].[Cs+].O1CCOCC1>C(OCC)(=O)C.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]>[CH3:17][N:12]([S:13]([CH3:16])(=[O:15])=[O:14])[C:10]1[CH:9]=[C:4]([CH:3]=[C:2]([N:27]2[CH2:28][CH:24]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH2:25][C:26]2=[O:29])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6]

참가 물질

7

반응물 4

HCID 10796Cesium carbonateHCID 312751,4-DioxaneHCID 1213974-Phenyl-2-pyrrolidinoneHCID 57529331Methyl 3-bromo-5-[methyl(methylsulfonyl)amino]benzoate

생성물 1

HCID 57815124Methyl 3-[methyl(methylsulfonyl)amino]-5-(2-oxo-4-phenylpyrrolidin-1-yl)benzoate수율 82%

시약·촉매·용매 2

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 8857Ethyl Acetate용매

반응 조건

온도
110 °C

실험 절차

A mixture of methyl 3-bromo-5-[methyl(methylsulfonyl)amino]benzoate obtained in Reference Example 15 322 mg (1.0 mmol), 4-phenyl-2-pyrrolidinone 177 mg (1.1 mmol), cesium carbonate 456 mg (1.4 mmol), tris(dibenzylideneacetone)dipalladium(0) 4.6 mg (0.005 mmol), Zandphos 8.7 mg (0.015 mmol) and 1,4-dioxane (2 mL) was stirred at 110° C. under argon atmosphere for 7 hours. The reaction solution was diluted with ethyl acetate and the resulting precipitates were filtered. The solvent was evaporated and the residual solid was purified by a column chromatography on silica gel (eluted with hexane/ethyl acetate=3:1→1:1) to give 329 mg (0.817 mmol) of the title compound (yield: 82%).

후처리

  1. customthe resulting precipitates
  2. filtrationwere filtered
  3. customThe solvent was evaporated
  4. customthe residual solid was purified by a column chromatography on silica gel (eluted with hexane/ethyl acetate=3:1→1:1)

출처 및 근거

ORD 기록
ord-aeaa676f33c5463f8539c4bef597e2ff
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07816387B2

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