Cesium carbonate → 4-(7-bromo-3-oxo-2H-isoquinolin-2-ylmethyl)benzoic acid tert-butyl ester

HRID 488772Notes

Reaction equation

HRID 488772 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([OH:12])[N:8]=[CH:9]2)=[CH:4][CH:3]=1.[C:13]([O:17][C:18](=[O:27])[C:19]1[CH:24]=[CH:23][C:22]([CH2:25]Br)=[CH:21][CH:20]=1)([CH3:16])([CH3:15])[CH3:14].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[C:13]([O:17][C:18](=[O:27])[C:19]1[CH:20]=[CH:21][C:22]([CH2:25][N:8]2[C:7](=[O:12])[CH:6]=[C:5]3[C:10]([CH:11]=[C:2]([Br:1])[CH:3]=[CH:4]3)=[CH:9]2)=[CH:23][CH:24]=1)([CH3:16])([CH3:15])[CH3:14]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 11414578Tert-butyl 4-(bromomethyl)benzoateHCID 178515312HCID 178515312, compound

Product 1

HCID 865911974-(7-bromo-3-oxo-2H-isoquinolin-2-ylmethyl)benzoic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 7-bromo-3-hydroxy-isoquinoline (7.02 g, 28.2 mmol) in dimethylformamide (75 mL) is treated with 4-bromomethylbenzoic acid tert-butyl ester (12.5 g, 36.7 mmol) and cesium carbonate (11.94 g, 36.7 mmol), then stirred overnight at room temperature. The dimethylformamide is evaporated in vacuo, the residue is diluted with ethyl acetate, washed with 1N HCl, the organic portion washed with brine, dried over MgSO4 and evaporated to dryness. The residue is triturated with hot hexanes/ethyl acetate, cooled to room temperature, and the solid is collected by filtration and dried to give the desired product.

Workup

  1. customThe dimethylformamide is evaporated in vacuo
  2. additionthe residue is diluted with ethyl acetate
  3. washwashed with 1N HCl
  4. washthe organic portion washed with brine
  5. dry with materialdried over MgSO4
  6. customevaporated to dryness
  7. customThe residue is triturated with hot hexanes/ethyl acetate
  8. temperaturecooled to room temperature
  9. filtrationthe solid is collected by filtration
  10. customdried

Sources & evidence

ORD record
ord-3bb28a6d36ba451bb65440e792949568
Source dataset
uspto-grants-2005_12
Patent number
US06974822B2

Reaction notes

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