Lithium Chloride → HCID 67386486, compound

HRID 1971458Notes

Reaction equation

HRID 1971458 reaction equation
FC(F)(F)S(O[C:7]1[C:16]2[C:11](=[C:12]([F:17])[CH:13]=[CH:14][CH:15]=2)[N:10]=[CH:9][CH:8]=1)(=O)=O.[Li+].[Cl-].[CH2:22]([O:24]C([Sn](CCCC)(CCCC)CCCC)=C)[CH3:23].C([O-])(O)=O.[Na+]>O1CCOCC1.ClCCl.C1COCC1>[F:17][C:12]1[CH:13]=[CH:14][CH:15]=[C:16]2[C:11]=1[N:10]=[CH:9][CH:8]=[C:7]2[C:22](=[O:24])[CH3:23]

Participants

8

Reactant 4

HCID 433294Lithium ChlorideHCID 516892Sodium BicarbonateHCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 87380534HCID 87380534, compound

Product 1

HCID 67386486HCID 67386486, compound

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolventHCID 312751,4-DioxaneSolvent

Procedure

1.3 g (4.4 mmol) 8-fluorochinoline-4-yl trifluoromethane sulfonate, 153 mg tetrakistriphenylphosphine palladium and 600 mg LiCl were suspended in a baked flask under protective gas in 30 ml dioxane, 1.6 g (4.43 mmol) (1-ethoxyvinyl)-tributylstannane was added, the mixture was heated for 2 hours at reflux. The mixture was diluted with dichloromethane, was washed with water, was dried (MgSO4) and was concentrated. The residue thus obtained was dissolved in 30 ml THF and, following addition 2 ml 5N HCL, was stirred for 3 hours at room temperature. For workup, the mixture was adjusted with saturated NaHCO3 solution to pH 11, was extracted with dichloromethane, the combined organic phases were washed with saturated NaCl solution and were dried with MgSO4. Purification by chromatography on silica gel (dichloromethane) yielded 700 mg; ESI-MS [M+H+]=190.05.

Workup

  1. temperaturethe mixture was heated for 2 hours
  2. temperatureat reflux
  3. washwas washed with water
  4. dry with materialwas dried (MgSO4)
  5. concentrationwas concentrated
  6. customThe residue thus obtained
  7. additionaddition 2 ml 5N HCL
  8. extractionwas extracted with dichloromethane
  9. washthe combined organic phases were washed with saturated NaCl solution
  10. dry with materialwere dried with MgSO4
  11. customPurification by chromatography on silica gel (dichloromethane)
  12. customyielded 700 mg

Sources & evidence

ORD record
ord-18ddea1d63844a5dadafa7f7a01d6140
Source dataset
uspto-grants-2013_04
Patent number
US08431604B2

Reaction notes

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