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Ethyl bromoacetate → ethyl 2-(2-cyano-3,5-dimethyl-4-(2-(pyrrolidin-1-ylsulfonyl)benzyl)-1H-pyrrol-1-yl)acetate

HRID 1189554
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HRID 1189554 반응식
[CH3:1][C:2]1[C:6]([CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[S:14]([N:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)(=[O:16])=[O:15])=[C:5]([CH3:22])[NH:4][C:3]=1[C:23]#[N:24].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34]>CCCC[N+](CCCC)(CCCC)CCCC.[I-].CN(C=O)C.C(OCC)(=O)C>[C:23]([C:3]1[N:4]([CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34])[C:5]([CH3:22])=[C:6]([CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[S:14]([N:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)(=[O:16])=[O:15])[C:2]=1[CH3:1])#[N:24]
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7

반응물 3

HCID 7748Ethyl bromoacetateHCID 10796Cesium carbonateHCID 672403263,5-dimethyl-4-(2-(pyrrolidin-1-ylsulfonyl)benzyl)-1H-pyrrole-2-carbonitrile

생성물 1

HCID 53245904ethyl 2-(2-cyano-3,5-dimethyl-4-(2-(pyrrolidin-1-ylsulfonyl)benzyl)-1H-pyrrol-1-yl)acetate수율 110%

시약·촉매·용매 3

HCID 67553Tetrabutylammonium Iodide
촉매
HCID 6228Dimethylformamide용매
HCID 8857Ethyl Acetate용매

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온도
60 °C

실험 절차

To a mixture of 3,5-dimethyl-4-(2-(pyrrolidin-1-ylsulfonyl)benzyl)-1H-pyrrole-2-carbonitrile (29.1 mg, 0.085 mmol), cesium carbonate (110 mg, 0.339 mmol), and TBAI (3.13 mg, 8.47 μmol) in DMF (424 μl), was added ethyl bromoacetate (14.15 μl, 0.127 mmol). The mixture was heated at 60° C. for 5 hours and then allowed to cool down to room temperature and diluted with ethyl acetate (100 ml). The resulting mixture was washed with water (50 ml×3), dried, filtered, and evaporated to give an oil. This crude oil was purified by column chromatography (0 to 50% ethyl acetate in hexanes) to give ethyl 2-(2-cyano-3,5-dimethyl-4-(2-(pyrrolidin-1-ylsulfonyl)benzyl)-1H-pyrrol-1-yl)acetate (40.0 mg, 0.093 mmol, 110% yield).

후처리

  1. temperatureto cool down to room temperature
  2. washThe resulting mixture was washed with water (50 ml×3)
  3. customdried
  4. filtrationfiltered
  5. customevaporated
  6. customto give an oil
  7. customThis crude oil was purified by column chromatography (0 to 50% ethyl acetate in hexanes)

출처 및 근거

ORD 기록
ord-9c247d32685a4bf6abd66a6325ea1818
출처 데이터셋
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08674115B2

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