Dimethylformamide → 7-bromo-4-chloro-2-(4-methoxybenzyl)isoquinolin-1(2H)-one

HRID 1473697Notes

Reaction equation

HRID 1473697 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([Cl:13])=[CH:7][NH:8][C:9]2=[O:12])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CN(C=O)C.Cl[CH2:26][C:27]1[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=1>O>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([Cl:13])=[CH:7][N:8]([CH2:26][C:27]3[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=3)[C:9]2=[O:12])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 699934-Methyloxybenzyl chlorideHCID 211924357-Bromo-4-chloroisoquinolin-1(2H)-one

Product 1

HCID 866877827-bromo-4-chloro-2-(4-methoxybenzyl)isoquinolin-1(2H)-oneYield 61.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

To a screw cap pressure vessel, 7-bromo-4-chloroisoquinolin-1(2H)-one (Ark Chemicals, 2.50 g, 9.67 mmol) was added to a vial followed by cesium carbonate (6.30 g, 19.34 mmol) and DMF (9.67 mL). 1-(chloromethyl)-4-methoxybenzene (1.444 ml, 10.64 mmol) was added, the vial was capped and heated to 50° C. for 1 hours. The reaction was cooled to room temperature and water (20 mL) was added. The reaction was stirred for an additional 1 hour and filtered. The solid was collected and dried under a vacuum to yield 2.25 g of 7-bromo-4-chloro-2-(4-methoxybenzyl)isoquinolin-1(2H)-one as an off white solid. m/z (ESI) 380.1 (M+H)+.

Workup

  1. customTo a screw cap pressure vessel
  2. customthe vial was capped
  3. temperatureThe reaction was cooled to room temperature
  4. filtrationfiltered
  5. customThe solid was collected
  6. customdried under a vacuum

Sources & evidence

ORD record
ord-7fbb56ce0c17465a9431078e951f277f
Source dataset
uspto-grants-2015_04
Patent number
US09012443B2

Reaction notes

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