Methanol → HCID 69156239、化合物

HRID 750146ノート

反応式

HRID 750146 の反応式
[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]

参加物

8

反応物 5

HCID 887MethanolHCID 6228DimethylformamideHCID 8471TriethylamineHCID 10239063HCID 10239063、化合物HCID 178418416HCID 178418416、化合物

生成物 1

HCID 69156239HCID 69156239、化合物

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)触媒

反応条件

温度
100 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-77b4ceba8696428d8565ca8de0721617
出典データセット
uspto-grants-2008_07
特許番号
US07402595B2

反応ノート

読み込み中…