Hydrochloric Acid → HCID 22493561, compound

HRID 1263461Notes

Reaction equation

HRID 1263461 reaction equation
C[Li].FC(F)(F)S(O[C:9]1[C:18]2[C:13](=[C:14]([CH:19]([CH3:21])[CH3:20])[CH:15]=[CH:16][CH:17]=2)[N:12]=[C:11]([C:22]([O:24][CH3:25])=[O:23])[CH:10]=1)(=O)=O.Cl.[C:29](OCC)(=O)C.CCCCCC>O1CCCC1.[Cl-].[Zn+2].[Cl-].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH:19]([C:14]1[CH:15]=[CH:16][CH:17]=[C:18]2[C:13]=1[N:12]=[C:11]([C:22]([O:24][CH3:25])=[O:23])[CH:10]=[C:9]2[CH3:29])([CH3:21])[CH3:20]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 21226206Ethyl acetate hexaneHCID 22493592HCID 22493592, compoundHCID 178418348HCID 178418348, compound

Product 1

HCID 22493561HCID 22493561, compound

Reagents, catalysts & solvents 3

HCID 3007855ZincchlorideCatalystHCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent3×

Procedure

In 30 ml of tetrahydrofuran were suspended 1.8 g of zinc chloride at room temperature under a nitrogen gas stream. A 1.4M tetrahydrofuran solution of methyl lithium (9.5 ml) was added dropwise to the resulting suspension and the resulting mixture was stirred for one hour. The reaction mixture was added dropwise to a solution of 1 g of methyl 4-trifluoromethanesulfonyloxy-8-isopropylquinoline-2-carboxylate and 153 mg of tetrakis(triphenylphosphine)palladium in 20 ml of tetrahydrofuran, followed by stirring at room temperature for 65 hours. Dilute hydrochloric acid was added to the reaction mixture and the resulting mixture was extracted with ethyl acetate. The organic layer was successively washed with water and saturated saline, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue so obtained was subjected to chromatography on a silica gel column (developing solvent: 2% ethyl acetate/n-hexane), whereby 125 mg of the title compound were obtained in the form of a colorless solid.

Workup

  1. customat room temperature
  2. stirringby stirring at room temperature for 65 hours
  3. extractionthe resulting mixture was extracted with ethyl acetate
  4. washThe organic layer was successively washed with water and saturated saline
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue so obtained

Sources & evidence

ORD record
ord-945012c8d8ff4f11b7fdc497ace7d2e0
Source dataset
uspto-grants-2003_04
Patent number
US06541474B2

Reaction notes

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