Sodium Iodide → 3-(6-Bromo-4-formyl-1-oxoisoquinolin-2(1H)-yl)-2,2-dimethylpropyl acetate

HRID 906401Notes

Reaction equation

HRID 906401 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[N:7]([CH2:13][C:14]([CH3:18])([CH3:17])[CH2:15]Cl)[CH:6]=[C:5]2[CH:19]=[O:20].[C:21]([O-:24])(=[O:23])[CH3:22].[Na+].[I-].[Na+]>CS(C)=O.O>[C:21]([O:24][CH2:15][C:14]([CH3:18])([CH3:17])[CH2:13][N:7]1[CH:6]=[C:5]([CH:19]=[O:20])[C:4]2[C:9](=[CH:10][CH:11]=[C:2]([Br:1])[CH:3]=2)[C:8]1=[O:12])(=[O:23])[CH3:22]

Participants

6

Reactant 3

HCID 5238Sodium IodideHCID 517045Sodium AcetateHCID 866409616-Bromo-2-(3-chloro-2,2-dimethylpropyl)-1-oxo-1,2-dihydroisoquinoline-4-carbaldehyde

Product 1

HCID 866409623-(6-Bromo-4-formyl-1-oxoisoquinolin-2(1H)-yl)-2,2-dimethylpropyl acetateYield 52.1%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 6-bromo-2-(3-chloro-2,2-dimethylpropyl)-1-oxo-1,2-dihydroisoquinoline-4-carbaldehyde (Example 1d, 0.45 g) in dimethylsulfoxide (10 mL) was treated with sodium acetate (0.343 g) under nitrogen. The resulting mixture was stirred at 100° C. for 10 h. Sodium iodide (1 eq) was added and the reaction heated at 120° C. for 30 h. The reaction mixture was diluted with water (250 mL) and the solid filtered off and dried to afford the subtitle compound (0.25 g) as a solid.

Workup

  1. temperaturethe reaction heated at 120° C. for 30 h
  2. filtrationthe solid filtered off
  3. customdried

Sources & evidence

ORD record
ord-d5795c67794b49098292ecddde65f42c
Source dataset
uspto-grants-2011_09
Patent number
US08012980B2

Reaction notes

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