Hydrochloric Acid → 1-Cyano-4-hydroxy-7-(pyridin-3-yloxy)-isoquinoline-3-carboxylic acid ethyl ester
Reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8](I)[C:9]2[C:14]([C:15]=1[OH:16])=[CH:13][CH:12]=[C:11]([O:17][C:18]1[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=1)[CH:10]=2)=[O:5])[CH3:2].[C:25]([Cu])#[N:26].Cl>CN1C(=O)CCC1.C(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([C:25]#[N:26])[C:9]2[C:14]([C:15]=1[OH:16])=[CH:13][CH:12]=[C:11]([O:17][C:18]1[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=1)[CH:10]=2)=[O:5])[CH3:2]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 120 °C
Procedure
A mixture of 4-hydroxy-1-iodo-7-(pyridin-3-yloxy)-isoquinoline-3-carboxylic acid ethyl ester (215 mg) and CuCN (89 mg) in NMP (2 mL) was heated at 120° C. for 2 h; the reaction was then cooled, diluted with DCM, and stirred at rt overnight; then diluted HCl solution was added and stirred for 1 h; the solids were filtered off, and DCM phase was separated, washed with water, and dil. NaCl solution, dried over anhydrous sodium sulphate, filtered, concentrated and the residue was column purified to give product (53 mg). LCMS ESI+: 336 (M+1)+.
Workup
- temperaturethe reaction was then cooled
- stirringstirred for 1 h
- filtrationthe solids were filtered off
- customDCM phase was separated
- washwashed with water, and dil. NaCl solution
- dry with materialdried over anhydrous sodium sulphate
- filtrationfiltered
- concentrationconcentrated
- custompurified
Sources & evidence
- ORD record
- ord-d61d45dc6b6c4c4da257ccfbc638c66c
- Source dataset
- uspto-grants-2016_08
- Patent number
- US09409892B2
Reaction notes
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