Methanol → HCID 69156239, 화합물

HRID 750146노트

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HRID 750146 반응식
[CH3:1][O:2][C:3]([C:5]1[N:6]([CH2:23][C:24]2[CH:32]=[CH:31][C:27]3[O:28][CH2:29][O:30][C:26]=3[CH:25]=2)[C:7](=[O:22])[C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:12][C:11](Br)=[CH:10][CH:9]=2)=[O:4].C(N(CC)CC)C.CN([CH:43]=[O:44])C.[C]=O.[CH3:47][OH:48]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[CH3:1][O:2][C:3]([C:5]1[N:6]([CH2:23][C:24]2[CH:32]=[CH:31][C:27]3[O:28][CH2:29][O:30][C:26]=3[CH:25]=2)[C:7](=[O:22])[C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:12][C:11]([C:47]([O:44][CH3:43])=[O:48])=[CH:10][CH:9]=2)=[O:4]

참가 물질

8

반응물 5

HCID 887MethanolHCID 6228DimethylformamideHCID 8471TriethylamineHCID 10239063HCID 10239063, 화합물HCID 178418416HCID 178418416, 화합물

생성물 1

HCID 69156239HCID 69156239, 화합물

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)촉매

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온도
100 °C

실험 절차

A mixture of 2-(benzo[1,3]dioxol-5-ylmethyl)-6-bromo-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic acid methyl ester (300 mg), palladium(II) acetate (7 mg), 1,1′-bis(diphenylphosphino)ferrocene (17 mg), triethylamine (0.22 ml), DMF (10 ml) and methanol (10 ml) was stirred at 100° C. for 6 hrs. under 5 atm carbon monoxide. The reaction mixture was concentrated, and water was added to the residue. The mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate) and the obtained crystals were washed with diisopropyl ether to give the title compound (250 mg).

후처리

  1. concentrationThe reaction mixture was concentrated
  2. additionwater was added to the residue
  3. extractionThe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with water and saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography (ethyl acetate)
  8. washthe obtained crystals were washed with diisopropyl ether

출처 및 근거

ORD 기록
ord-77b4ceba8696428d8565ca8de0721617
출처 데이터셋
uspto-grants-2008_07
특허 번호
US07402595B2

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