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Sodium Carbonate → 1,1-Dimethylethyl 3-(5-cyano-1-isoquinolinyl)propanoate

HRID 2192491
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HRID 2192491 반응식
Br[C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][N:6]=[C:7]2[CH2:12][CH2:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15].C(=O)([O-])[O-].[Na+].[Na+].C[C:28]([N:30](C)C)=O>C(OCC)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:28]([C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][N:6]=[C:7]2[CH2:12][CH2:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])#[N:30]
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참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 31374DimethylacetamideHCID 581499231,1-Dimethylethyl 3-(5-bromo-1-isoquinolinyl)propanoate

생성물 1

HCID 581499281,1-Dimethylethyl 3-(5-cyano-1-isoquinolinyl)propanoate

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 8857
Ethyl Acetate
용매

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온도
120 °C

실험 절차

1,1-Dimethylethyl 3-(5-bromo-1-isoquinolinyl)propanoate (D34; 60 g, 178 mmol) was taken up in dry DMA (600 ml) followed by the addition of potassium hexacyanoferrate hexahydrate (22.61 g, 53.5 mmol) then palladium acetate (0.801 g, 3.57 mmol) dppf (3.96 g, 7.14 mmol) and then finally sodium carbonate (22.7 g, 214 mmol). The reaction mixture was stirred at 120° C. overnight, cooled and diluted with ethyl acetate (500 ml) and filtered through Celite. The filtrate was concentrated in vacuo. and the dark residue was taken up in DCM (250 ml) and filtered through Celite and cotton wool. The DCM solution (250 ml) was purified by chromatography using a gradient system 0-100% ethyl acetate in isohexane to give the title compound (25.3 g)

후처리

  1. temperaturecooled
  2. filtrationfiltered through Celite
  3. concentrationThe filtrate was concentrated in vacuo
  4. filtrationfiltered through Celite and cotton wool
  5. customThe DCM solution (250 ml) was purified by chromatography

출처 및 근거

ORD 기록
ord-60902b9976b64e0da0c5507f0d5ae86e
출처 데이터셋
uspto-grants-2012_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08329730B2

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