Benzyl Bromide → Methyl 5-(2-benzyl-6-bromo-1-oxo-1,2-dihydroisoquinolin-3-yl)pentanoate

HRID 927264Notes

Reaction equation

HRID 927264 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:9][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[C:16](=[O:20])[NH:15][C:14]([CH2:21][CH2:22][CH2:23][CH2:24][C:25]([O:27][CH3:28])=[O:26])=[CH:13]2.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.O>[CH2:1]([N:15]1[C:14]([CH2:21][CH2:22][CH2:23][CH2:24][C:25]([O:27][CH3:28])=[O:26])=[CH:13][C:12]2[C:17](=[CH:18][CH:19]=[C:10]([Br:9])[CH:11]=2)[C:16]1=[O:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 118558135Methyl 5-(6-bromo-1-oxo-1,2-dihydroisoquinolin-3-yl)pentanoate

Product 1

HCID 118558145Methyl 5-(2-benzyl-6-bromo-1-oxo-1,2-dihydroisoquinolin-3-yl)pentanoateYield 58.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Benzyl bromide (152 mg, 0.887 mmol, 1.50 equiv.) was added to a stirred mixture of methyl 5-(6-bromo-1-oxo-1,2-dihydroisoquinolin-3-yl)pentanoate (200 mg, 0.591 mmol) and Cs2CO3 (289 mg, 0.887 mmol, 1.50 equiv.) in DMF (1 mL) and the mixture was stirred at room temperature overnight. Upon completion, the reaction mixture was diluted with water, extracted with EtOAc (2×5 mL), washed with brine, dried over Na2SO4, filtered and evaporated to dryness. The residue was purified by column chromatography on silica gel, eluting with 0-20% EtOAc/hexanes to give 147 mg of methyl 5-(2-benzyl-6-bromo-1-oxo-1,2-dihydroisoquinolin-3-yl)pentanoate as a pink solid.

Workup

  1. extractionextracted with EtOAc (2×5 mL)
  2. washwashed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customThe residue was purified by column chromatography on silica gel
  7. washeluting with 0-20% EtOAc/hexanes

Sources & evidence

ORD record
ord-fa968288332f4fb4b93eeb5c261120b3
Source dataset
uspto-grants-2016_03
Patent number
US09290454B2

Reaction notes

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