Water → HCID 58452680, compound

HRID 70499Notes

Reaction equation

HRID 70499 reaction equation
[F-].[CH2:2]([N+](CCCC)(CCCC)CCCC)[CH2:3][CH2:4]C.[Si]([O:26][C:27]1[CH:32]=[CH:31][C:30]([C:33]([C:35]2[CH:40]=[CH:39][C:38]([Cl:41])=[C:37]([O:42][CH3:43])[N:36]=2)=[O:34])=[CH:29][C:28]=1[Cl:44])(C(C)(C)C)(C)C.O>O1CCCC1>[Cl:41][C:38]1[CH:39]=[CH:40][C:35]([C:33]([C:30]2[CH:31]=[CH:32][C:27]([O:26][CH:3]([CH3:4])[CH3:2])=[C:28]([Cl:44])[CH:29]=2)=[O:34])=[N:36][C:37]=1[O:42][CH3:43]

Participants

5

Reactant 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 67398382HCID 67398382, compound

Product 1

HCID 58452680HCID 58452680, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A 1 M solution of tetrabutylammonium fluoride in tetrahydrofuran (3.39 mL) was added to a solution of (4-{[tert-butyl(dimethyl)silyl]oxy}-3-chlorophenyl)(5-chloro-6-methoxypyridin-2-yl)methanone (700 mg) in tetrahydrofuran (10 mL) at room temperature, and the mixture was stirred at room temperature for two hours. Water was added to the reaction solution, followed by extraction with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and filtered, after which the filtrate was concentrated under reduced pressure. The resulting residue was dissolved in N,N-dimethylformamide (10 mL), and 2-iodopropane (333 μL) and potassium carbonate (464 mg) were sequentially added at room temperature, followed by stirring at 65° C. for three hours. The reaction solution was returned to room temperature and water was added, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and filtered. The solvent was then evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=30:1) to give the title compound as a colorless oil (538 mg, 93%).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationafter which the filtrate was concentrated under reduced pressure
  6. dissolutionThe resulting residue was dissolved in N,N-dimethylformamide (10 mL)
  7. addition2-iodopropane (333 μL) and potassium carbonate (464 mg) were sequentially added at room temperature
  8. stirringby stirring at 65° C. for three hours
  9. customwas returned to room temperature
  10. additionwater was added
  11. extractionfollowed by extraction with ethyl acetate
  12. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  13. filtrationfiltered
  14. customThe solvent was then evaporated under reduced pressure
  15. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=30:1)

Sources & evidence

ORD record
ord-523e9280f8d941199105ee55ae7dc765
Source dataset
uspto-grants-2014_09
Patent number
US08822503B2

Reaction notes

Loading…