Dimethylformamide → HCID 23158299, compound

HRID 601688Notes

Reaction equation

HRID 601688 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.[F:20][CH:21]([F:24])[CH2:22]I>O>[Br:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[C:15](=[O:19])[N:14]([CH2:22][CH:21]([F:24])[F:20])[CH:13]=[CH:12]2

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 38335651,1-Difluoro-2-iodoethaneHCID 158851826-Bromoisoquinolin-1(2H)-one

Product 1

HCID 23158299HCID 23158299, compoundYield 65.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Under nitrogen atmosphere, 44 mg of 60% sodium hydride was added at room temperature to 2 ml solution of dimethylformamide with 49 mg of 6-bromo-2H-isoquinoline-1-one and the mixture was stirred for 30 min. Then, 169 mg of 2,2-difluoroethyliodide was added and stirred at room temperature for 6 hours. Cold water was added to the reaction solution, the products were extracted with chloroform. Chloroform layer was washed with saturated saline solution and dried with anhydrous sodium sulfate. The solvents were distilled outunder reduced pressure, and the residues were separated and purified by thin-layer chromatography (chloroform/methyl alcohol=10/1) to obtain 41 mg of the above compound as a white solid.

Workup

  1. stirringstirred at room temperature for 6 hours
  2. extractionthe products were extracted with chloroform
  3. washChloroform layer was washed with saturated saline solution
  4. dry with materialdried with anhydrous sodium sulfate
  5. distillationThe solvents were distilled outunder reduced pressure
  6. customthe residues were separated
  7. custompurified by thin-layer chromatography (chloroform/methyl alcohol=10/1)

Sources & evidence

ORD record
ord-efe269aef93d4c529c0b221c574e3bef
Source dataset
uspto-grants-2011_03
Patent number
US07902369B2

Reaction notes

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