Sodium Iodide → HCID 89586480, compound

HRID 333745Notes

Reaction equation

HRID 333745 reaction equation
[I-].[Na+].Cl[Si](C)(C)C.[CH3:8][O:9][C:10]1[C:11](=[O:26])[CH:12]=[N:13][N:14]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[CH:17]=2)[CH:15]=1.[C:27](#[N:29])[CH3:28]>O>[N:29]1[C:19]2[C:18](=[CH:17][CH:16]=[CH:21][CH:20]=2)[CH:22]=[CH:28][C:27]=1[CH2:8][O:9][C:10]1[C:11](=[O:26])[CH:12]=[N:13][N:14]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:25])([F:23])[F:24])[CH:17]=2)[CH:15]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 6342Acetonitrile2×HCID 6397ChlorotrimethylsilaneHCID 89586364HCID 89586364, compound

Product 1

HCID 89586480HCID 89586480, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Sodium iodide (0.2772 g) and chlorotrimethylsilane (0.235 mL) were stirred in acetonitrile (1.85 mL) at room temperature for 30 min. A solution of 5-methoxy-1-[3-(trifluoromethyl)phenyl]pyridazin-4(1H)-one (0.100 g) in acetonitrile (3.7 mL) was added at room temperature. The reaction mixture was heated under reflux for 3 hr. The reaction mixture was cooled to room temperature, diluted with water, and extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate and filtered, and the filtrate was concentrated, purified by silica gel column chromatography (ethyl acetate/hexane-methanol/ethyl acetate), and concentrated under reduced pressure. The obtained residue, potassium carbonate (0.1125 g) and 2-(chloromethyl)quinoline hydrochloride (0.0871 g) were suspended in N,N-dimethylformamide (2 mL), and the mixture was stirred at room temperature for 14 hr, and at 60° C. for 5 hr. The reaction mixture was cooled to room temperature, diluted with water, and extracted with ethyl acetate. The extract was washed with brine, dried over anhydrous sodium sulfate and filtered, and the filtrate was concentrated. The residue was purified by NH silica gel column chromatography (ethyl acetate/hexane), silica gel column chromatography (ethyl acetate/hexane) and HPLC, and recrystallized from ethyl acetate/hexane to give the title compound (0.0527 g).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 3 hr
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated
  8. custompurified by silica gel column chromatography (ethyl acetate/hexane-methanol/ethyl acetate)
  9. concentrationconcentrated under reduced pressure
  10. waitat 60° C. for 5 hr
  11. temperatureThe reaction mixture was cooled to room temperature
  12. additiondiluted with water
  13. extractionextracted with ethyl acetate
  14. washThe extract was washed with brine
  15. dry with materialdried over anhydrous sodium sulfate
  16. filtrationfiltered
  17. concentrationthe filtrate was concentrated
  18. customThe residue was purified by NH silica gel column chromatography (ethyl acetate/hexane), silica gel column chromatography (ethyl acetate/hexane) and HPLC
  19. customrecrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-4f89eb8161364fbb95b83039483c9d99
Source dataset
uspto-grants-2014_11
Patent number
US08883788B2

Reaction notes

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