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

HRID 1616106노트

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HRID 1616106 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
60 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-0690bd31ea0844c29ae17bb213349543
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08765773B2

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