Water → 6-bromo-2-(6-chloropyridin-3-ylmethyl)-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic Acid Methyl Ester

HRID 750179ノート

反応式

HRID 750179 の反応式
[CH3:1][O:2][C:3]([C:5]1[NH:6][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:21])=[CH:10][CH:9]=2)=[O:4].[H-].[Na+].[Cl:25][C:26]1[CH:31]=[CH:30][C:29]([CH2:32]Cl)=[CH:28][N:27]=1.O>CN(C=O)C>[CH3:1][O:2][C:3]([C:5]1[N:6]([CH2:32][C:29]2[CH:28]=[N:27][C:26]([Cl:25])=[CH:31][CH:30]=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:21])=[CH:10][CH:9]=2)=[O:4]

参加物

6

反応物 4

HCID 962WaterHCID 24758Sodium hydrideHCID 1554792-Chloro-5-(chloromethyl)pyridineHCID 691573826-bromo-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic Acid Methyl Ester

生成物 1

HCID 865995546-bromo-2-(6-chloropyridin-3-ylmethyl)-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic Acid Methyl Ester収率 30.6%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 6-bromo-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic acid methyl ester (290 mg) in DMF (3 ml) was added sodium hydride (60% in oil, 36 mg) under ice-cooling, and the mixture was allowed to warm to room temperature and stirred for 1 hr. To the reaction mixture was added 2-chloro-5-chloromethylpyridine (160 mg) at room temperature, and the mixture was stirred for 2 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, and dried. The solvent was evaporated under reduced pressure and the obtained residue was crystallized from ethyl acetate to give the title compound (120 mg).

後処理

  1. temperaturecooling
  2. stirringthe mixture was stirred for 2 hrs
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with water and saturated brine
  5. customdried
  6. customThe solvent was evaporated under reduced pressure
  7. customthe obtained residue was crystallized from ethyl acetate

出典と根拠

ORDレコード
ord-60fe625ff5fa41fca0b94af3391b15c4
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…