Sodium hydride → 6-bromo-2-(3-methoxycarbonylbenzyl)-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic Acid Methyl Ester

HRID 750133ノート

反応式

HRID 750133 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+].[CH3:25][O:26][C:27](=[O:36])[C:28]1[CH:33]=[CH:32][CH:31]=[C:30]([CH2:34]Br)[CH:29]=1>CN(C)C=O>[CH3:1][O:2][C:3]([C:5]1[N:6]([CH2:34][C:30]2[CH:31]=[CH:32][CH:33]=[C:28]([C:27]([O:26][CH3:25])=[O:36])[CH:29]=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

5

反応物 3

HCID 24758Sodium hydrideHCID 517981Methyl 3-(bromomethyl)benzoateHCID 691573826-bromo-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic Acid Methyl Ester

生成物 1

HCID 444516386-bromo-2-(3-methoxycarbonylbenzyl)-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic Acid Methyl Ester収率 39.1%

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 (1.30 g) in dimethylformamide (20 ml) was added sodium hydride (oil, 216 mg), and the mixture was stirred at room temperature for 20 min. 3-Bromomethylbenzoic acid methyl ester (990 mg) was added and the mixture was stirred at room temperature for 5 hrs. The solvent was evaporated under reduced pressure and 1N hydrochloric acid was added, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine and dried by adding sodium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=19/1→4/1) to give the title compound (719 mg, 39%).

後処理

  1. stirringthe mixture was stirred at room temperature for 5 hrs
  2. customThe solvent was evaporated under reduced pressure and 1N hydrochloric acid
  3. additionwas added
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe extract was washed with saturated brine
  6. customdried
  7. additionby adding sodium sulfate
  8. customThe solvent was evaporated under reduced pressure
  9. customthe obtained residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=19/1→4/1)

出典と根拠

ORDレコード
ord-5921542135014c079c5775ac13bf96ef
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…