Benzyl Bromide → Methyl 2-benzyl-1-oxo-1,2-dihydroisoquinoline-7-carboxylate

HRID 1616106ノート

反応式

HRID 1616106 の反応式
[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([O:14][CH3:15])=[O:13])[CH:10]=2)[CH:5]=[CH:4][NH:3]1.C(=O)([O-])[O-].[K+].[K+].[CH2:22](Br)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>CN(C=O)C>[CH2:22]([N:3]1[CH:4]=[CH:5][C:6]2[C:11](=[CH:10][C:9]([C:12]([O:14][CH3:15])=[O:13])=[CH:8][CH:7]=2)[C:2]1=[O:1])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

参加物

5

反応物 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 60075037Methyl 1-oxo-1,2-dihydroisoquinoline-7-carboxylate

生成物 1

HCID 67282484Methyl 2-benzyl-1-oxo-1,2-dihydroisoquinoline-7-carboxylate

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

To a solution of methyl 1-oxo-1,2-dihydroisoquinoline-7-carboxylate (32.5 mg, 0.16 mmol) in DMF (1.50 mL) was added potassium carbonate (66 mg, 0.48 mmol) and benzyl bromide (38.1 μL, 0.32 mmol). The reaction mixture was heated to 60° C. and stirred for 5 h. The mixture was then cooled to rt and concentrated. Water was added and the reaction mixture was extracted with DCM (5 mL, 3×). The combined organic phases were then washed with water, and brine, dried over anhydrous Na2SO4, filtered and concentrated to afford methyl 2-benzyl-1-oxo-1,2-dihydroisoquinoline-7-carboxylate. LC-MS: (FA) ES+ 294.

後処理

  1. temperatureThe mixture was then cooled to rt
  2. concentrationconcentrated
  3. additionWater was added
  4. extractionthe reaction mixture was extracted with DCM (5 mL, 3×)
  5. washThe combined organic phases were then washed with water, and brine
  6. dry with materialdried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-0690bd31ea0844c29ae17bb213349543
出典データセット
uspto-grants-2014_07
特許番号
US08765773B2

反応ノート

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