Methanol → 2-benzyl-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3,6-dicarboxylic Acid Dimethyl Ester

HRID 750162

반응식

HRID 750162 반응식
[CH3:1][O:2][C:3]([C:5]1[N:6]([CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][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:40]=[O:41])C.[C]=O.[CH3:44][OH:45]>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].O>[CH3:1][O:2][C:3]([C:5]1[N:6]([CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][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:44]([O:41][CH3:40])=[O:45])=[CH:10][CH:9]=2)=[O:4]

참가 물질

9

반응물 5

HCID 887MethanolHCID 6228DimethylformamideHCID 8471TriethylamineHCID 444516902-benzyl-6-bromo-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic Acid Methyl EsterHCID 178418416HCID 178418416, 화합물

생성물 1

HCID 691557242-benzyl-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3,6-dicarboxylic Acid Dimethyl Ester

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)촉매HCID 962Water용매

실험 절차

A mixture of 2-benzyl-6-bromo-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic acid methyl ester (300 mg), palladium(II) acetate (8 mg), 1,1′-bis(diphenylphosphino)ferrocene (20 mg), triethylamine (0.23 ml), DMF (3 ml) and methanol (3 ml) was stirred at 50° C. under 1 atm carbon monoxide for 24 hrs. Water was added to the reaction mixture, and 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 (hexane-hexane:ethyl acetate=2:1) and recrystallized (ethyl acetate-hexane) to give the title compound (180 mg).

후처리

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (hexane-hexane:ethyl acetate=2:1)
  6. customrecrystallized (ethyl acetate-hexane)

출처 및 근거

ORD 기록
ord-189f2da5b5564b739a175d34814b40e2
출처 데이터셋
uspto-grants-2008_07
특허 번호
US07402595B2

연결된 노트

불러오는 중…