HCID 86617064, compound → HCID 67110198, compound

HRID 409208Notes

Reaction equation

HRID 409208 reaction equation
[CH2:1]([O:5][C:6]([C:8]1[N:9]=[C:10](Br)[C:11]2[C:16]([C:17]=1[OH:18])=[CH:15][C:14]([O:19][CH3:20])=[CH:13][CH:12]=2)=[O:7])[CH2:2][CH2:3][CH3:4].[Cu][C:23]#[N:24]>CN(C)C=O>[CH2:1]([O:5][C:6]([C:8]1[N:9]=[C:10]([C:23]#[N:24])[C:11]2[C:16]([C:17]=1[OH:18])=[CH:15][C:14]([O:19][CH3:20])=[CH:13][CH:12]=2)=[O:7])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 86617064HCID 86617064, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 67110198HCID 67110198, compoundYield 48.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1-bromo-4-hydroxy-6-methoxy-isoquinoline-3-carboxylic acid butyl ester (290 mg, 0.82 mmol) and copper(I) cyanide (147 mg, 1.64 mmol) in anhydrous dimethylformamide (4 mL) was refluxed for ten minutes before it was cooled to room temperature and quenched with water. The resulting slurry was stirred with chloroform/isopropanol (3:1, 40 mL) and water for ten minutes and was then filtered. The organic layer of the filtrate was separated, washed with water, and brine, before it was dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel with a gradient of methanol and dichloromethane to give the title compound as a white solid (120 mg): MS: (+) m/z 301.01 (M+1).

Workup

  1. temperaturewas refluxed for ten minutes before it
  2. customquenched with water
  3. filtrationwas then filtered
  4. customThe organic layer of the filtrate was separated
  5. washwashed with water, and brine, before it
  6. dry with materialwas dried over anhydrous sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by flash column chromatography on silica gel with a gradient of methanol and dichloromethane

Sources & evidence

ORD record
ord-0afef3e3e6fe4b1e9660eca7bcffdd19
Source dataset
uspto-grants-2014_06
Patent number
US08759373B2

Reaction notes

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