Dimethylformamide → HCID 23158301, compound

HRID 601669Notes

Reaction equation

HRID 601669 reaction equation
[H-].[Na+].CN(C)C=O.[Br:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[C:15](=[O:19])[NH:14][CH:13]=[CH:12]2.[CH:20](I)([CH3:22])[CH3:21]>O>[Br:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[C:15](=[O:19])[N:14]([CH:20]([CH3:22])[CH3:21])[CH:13]=[CH:12]2

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6362Isopropyl iodideHCID 24758Sodium hydrideHCID 158851826-Bromoisoquinolin-1(2H)-one

Product 1

HCID 23158301HCID 23158301, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Under nitrogen atmosphere, 18 mg of 60% sodium hydride was added at 0° C. to 2 ml solution of dimethylformamide with 100 mg of 6-bromo-2H-isoquinoline-1-one, and the mixture was stirred for 30 min. 0.05 ml of isopropyl iodide was added at 0° C., and the mixture was stirred at room temperature for 2 hours. Cold water was added to the reaction solution, extracted with chloroform. Chloroform layer was washed with saturated saline solution, and dried with anhydrous sodium sulfate. After distilling out the solvents under reduced pressure, residues were separated and purified by thin-layer chromatography (hexane/ethyl acetate=3/1) to obtain 17 mg of the above compound.

Workup

  1. stirringthe mixture was stirred at room temperature for 2 hours
  2. extractionextracted with chloroform
  3. washChloroform layer was washed with saturated saline solution
  4. dry with materialdried with anhydrous sodium sulfate
  5. distillationAfter distilling out the solvents under reduced pressure, residues
  6. customwere separated
  7. custompurified by thin-layer chromatography (hexane/ethyl acetate=3/1)

Sources & evidence

ORD record
ord-7df78b4f28984829a6d63e183e2bc5fc
Source dataset
uspto-grants-2011_03
Patent number
US07902369B2

Reaction notes

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