Potassium Carbonate → 2-(Isoquinolin-7-yloxy)-2-methyl-propionic acid ethyl ester

HRID 1611412Notes

Reaction equation

HRID 1611412 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][N:8]=[CH:9]2)=[CH:4][CH:3]=1.Br[C:13]([CH3:20])([CH3:19])[C:14]([O:16][CH2:17][CH3:18])=[O:15].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:17]([O:16][C:14](=[O:15])[C:13]([O:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][N:8]=[CH:9]2)=[CH:4][CH:3]=1)([CH3:20])[CH3:19])[CH3:18]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11745Propanoic acid, 2-bromo-2-methyl-, ethyl esterHCID 4597677-Isoquinolinol

Product 1

HCID 235914662-(Isoquinolin-7-yloxy)-2-methyl-propionic acid ethyl esterYield 53.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
95 °C

Procedure

7-Hydroxyisoquinoline (500 mg, 3.4 mmol), ethyl 2-bromoisobutyrate (3 g, 15 mmol) and potassium carbonate (2.1 g, 15 mmol) were mixed in 7 ml of anhydrous DMF. The reaction was heated to 95° C. under N2 for 18 hrs. The reaction was concentrated under reduced pressure and purified by flash column chromatography (33% EtOAc/Hexanes) to yield 470 mg (53%) of the title product of this preparation as a yellow oil.

Workup

  1. concentrationThe reaction was concentrated under reduced pressure
  2. custompurified by flash column chromatography (33% EtOAc/Hexanes)
  3. customto yield

Sources & evidence

ORD record
ord-9ea8ce77ec37472da4ba10728e4e34ff
Source dataset
uspto-grants-2006_01
Patent number
US06987118B2

Reaction notes

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