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Dimethylformamide → 1,1-Dimethylethyl 1-[2-(butyloxy)-2-oxoethyl]-6-cyano-5-methyl-3,4-dihydro-2(1H)-isoquinolinecarboxylate

HRID 2383308
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HRID 2383308 반응식
[CH2:1]([O:5][C:6](=[O:34])[CH2:7][CH:8]1[C:17]2[C:12](=[C:13]([CH3:26])[C:14](OS(C(F)(F)F)(=O)=O)=[CH:15][CH:16]=2)[CH2:11][CH2:10][N:9]1[C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:2][CH2:3][CH3:4].[CH3:35][N:36](C)C=O>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[C-]#N.[Zn+2].[C-]#N>[CH2:1]([O:5][C:6](=[O:34])[CH2:7][CH:8]1[C:17]2[C:12](=[C:13]([CH3:26])[C:14]([C:35]#[N:36])=[CH:15][CH:16]=2)[CH2:11][CH2:10][N:9]1[C:27]([O:29][C:30]([CH3:32])([CH3:33])[CH3:31])=[O:28])[CH2:2][CH2:3][CH3:4]
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참가 물질

5

반응물 2

HCID 6228DimethylformamideHCID 595910841,1-Dimethylethyl 1-[2-(butyloxy)-2-oxoethyl]-5-methyl-6-{[(trifluoromethyl)sulfonyl]oxy}-3,4-dihydro-2(1H)-isoquinolinecarboxylate

생성물 1

HCID 595910861,1-Dimethylethyl 1-[2-(butyloxy)-2-oxoethyl]-6-cyano-5-methyl-3,4-dihydro-2(1H)-isoquinolinecarboxylate

시약·촉매·용매 2

HCID 11186Zinc cyanide (Zn(CN)2)촉매
HCID 178418397
HCID 178418397, 화합물
촉매

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온도
100 °C

실험 절차

A solution of 1,1-dimethylethyl 1-[2-(butyloxy)-2-oxoethyl]-5-methyl-6-{[(trifluoromethyl)sulfonyl]oxy}-3,4-dihydro-2(1H)-isoquinolinecarboxylate (Preparation 17; 837 mg, 1.64 mmol) in N,N-dimethylformamide (6 ml) was degassed under vacuum for 15 min. Tetrakis(triphenylphosphine)palladium(0) (190 mg, 0.164 mmol) and zinc cyanide (251 mg, 2.13 mmol) were then added and the resulting orange mixture stirred at 100° C. for 4 h. The mixture was cooled to room temperature and insoluble material filtered off and washed with ethyl acetate. The mother liquors were concentrated in vacuo and the residue dissolved in ethyl acetate. The solution was washed with saturated sodium bicarbonate and the aqueous phase further extracted twice with ethyl acetate. The combined organic phases were washed with brine, dried over MgSO4 and concentrated in vacuo. Purification by flash chromatography on silica gel, eluting with 5-25% ethyl acetate in cyclohexane, gave the title compound (600 mg) as a colourless oil.

후처리

  1. temperatureThe mixture was cooled to room temperature
  2. filtrationinsoluble material filtered off
  3. washwashed with ethyl acetate
  4. concentrationThe mother liquors were concentrated in vacuo
  5. dissolutionthe residue dissolved in ethyl acetate
  6. washThe solution was washed with saturated sodium bicarbonate
  7. extractionthe aqueous phase further extracted twice with ethyl acetate
  8. washThe combined organic phases were washed with brine
  9. dry with materialdried over MgSO4
  10. concentrationconcentrated in vacuo
  11. customPurification by flash chromatography on silica gel
  12. washeluting with 5-25% ethyl acetate in cyclohexane

출처 및 근거

ORD 기록
ord-7d0b1ee3565e498697183270d88c4c15
출처 데이터셋
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08263620B2

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