Cesium carbonate → 7-bromo-2-(3,5-difluoro-4-hydroxybenzyl)-2H-isoquinolin-3-one

HRID 488785Notes

Reaction equation

HRID 488785 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.Br[CH2:14][C:15]1[CH:20]=[C:19]([F:21])[C:18]([OH:22])=[C:17]([F:23])[CH:16]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][N:8]([CH2:14][C:15]1[CH:20]=[C:19]([F:21])[C:18]([OH:22])=[C:17]([F:23])[CH:16]=1)[C:7](=[O:12])[CH:6]=2

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 222653224-(Bromomethyl)-2,6-difluorophenolHCID 178515312HCID 178515312, compound

Product 1

HCID 222682637-bromo-2-(3,5-difluoro-4-hydroxybenzyl)-2H-isoquinolin-3-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The alkylation of 7-bromo-3-hydroxy-isoquinoline (1.30 g, 5.80 mmol) using 4-bromomethyl-2,6-difluorophenol (1.68 g, 7.54 mmol) and cesium carbonate (2.46 g, 7.54 mmol) in dimethyl-formamide is carried out as previously described in Example 1, Step (1). The solid is collected by filtration, washed with water, ethyl acetate, and allowed to air dry under house vacuum. Drying will afford the desired product. Step (2): 2-(3,5-difluoro-4-hydroxybenzyl)-7-[3-(4H-[1,2,3]triazol-4-yl)prop-1-ynyl]-2H-isoquinolin-3-one

Workup

  1. filtrationThe solid is collected by filtration
  2. washwashed with water, ethyl acetate
  3. customto air dry under house vacuum
  4. customDrying will

Sources & evidence

ORD record
ord-8eb7645f4e804a87a5da56d567a28410
Source dataset
uspto-grants-2005_12
Patent number
US06974822B2

Reaction notes

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