Cesium carbonate → HCID 67281879, compound

HRID 1616157Notes

Reaction equation

HRID 1616157 reaction equation
[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-].[Cs+].[Cs+].[Br:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([CH2:30]Br)[CH:25]=1>CN(C=O)C.O>[Br:22][CH2:23][C:24]1[CH:25]=[C:26]([CH:27]=[CH:28][CH:29]=1)[CH2:30][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]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 69373Benzene, 1,3-bis(bromomethyl)-HCID 60075037Methyl 1-oxo-1,2-dihydroisoquinoline-7-carboxylate

Product 1

HCID 67281879HCID 67281879, compoundYield 42%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of methyl 1-oxo-1,2-dihydroisoquinoline-7-carboxylate (0.15 g, 0.74 mmol) in DMF (7.5 mL) was added cesium carbonate (0.72 g, 2.2 mmol) and 1,3-bis(bromomethyl)benzene (0.29 g, 1.1 mmol). The reaction mixture was stirred at rt overnight. The mixture was diluted with water and extracted with EtOAc (2×). The combined organic phases were then washed with water, and brine, dried over anhydrous Na2SO4, filtered and concentrated. The residue was purified by flash silica gel chromatography (0% to 5% EtOAc/DCM) to afford methyl 2-[3-(bromomethyl)benzyl]-1-oxo-1,2-dihydroisoquinoline-7-carboxylate (0.12 g, 42%). LC-MS: (FA) ES+ 388.

Workup

  1. extractionextracted with EtOAc (2×)
  2. washThe combined organic phases were then washed with water, and brine
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by flash silica gel chromatography (0% to 5% EtOAc/DCM)

Sources & evidence

ORD record
ord-86240570b0f149f9abb69583588f0924
Source dataset
uspto-grants-2014_07
Patent number
US08765773B2

Reaction notes

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