Pyridine → HCID 22222475, compound

HRID 1794642Notes

Reaction equation

HRID 1794642 reaction equation
[CH2:1]([C:3]1[C:12]([CH3:13])=[C:11]([O:14][C:15]([CH:17]2[CH2:19][CH2:18]2)=[O:16])[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([F:21])[C:9]=2[F:20])[N:4]=1)C.[Cl-].ClC1N(C)CC[NH+]1C.N1C=C[CH:34]=[CH:33][CH:32]=1.C(C1C(C)=C([O:50]C(C2CC2)=O)C2C(=CC(F)=C(F)C=2)N=1)C>ClCCl.O>[CH3:1][C:3]1[C:12]([CH3:13])=[C:11]([O:14][C:15]([C:17](=[O:50])[CH2:19][CH2:18][CH2:32][C:33]#[CH:34])=[O:16])[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([F:21])[C:9]=2[F:20])[N:4]=1

Participants

7

Reactant 4

HCID 1049PyridineHCID 9857197HCID 9857197, compound2×HCID 109867151H-Imidazolium, 2-chloro-4,5-dihydro-1,3-dimethyl-, chlorideHCID 22222485HCID 22222485, compound2×

Product 1

HCID 22222475HCID 22222475, compoundYield 254.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

5-Hexynoic acid (starting material 2) (26.9 mg), 40.6 mg of 2-chloro-1,3-dimethylimidazolinium chloride and 37.9 mg of pyridine were stirred in dichloromethane (5 ml) at room temperature for one hr. Thereafter, 50 mg of 2,3-dimethyl-4-hydroxy-5,6-difluoroquinoline (starting material 1) prepared as described in Example 12 was added thereto, and the mixture was stirred at room temperature for 15 hr. Water was added to the reaction solution, and the mixture was extracted with dichloromethane. The dichloromethane layer was washed with a saturated aqueous sodium hydrogencarbonate solution and was then dried over anhydrous sodium sulfate. The solvent was then removed by evaporation under the reduced pressure. The crude product thus obtained was purified on Wako Gel C-200 (10 ml; elution solvent=n-hexane-ethyl acetate (10:1)) to give 77.8 mg of 2,3-dimethyl-4-(5-hexynoylcarbonyloxy)-5,6-difluoroquinoline (compound 58). 1H-NMR data are shown in Table 3.

Workup

  1. additionwas added
  2. extractionthe mixture was extracted with dichloromethane
  3. washThe dichloromethane layer was washed with a saturated aqueous sodium hydrogencarbonate solution
  4. dry with materialwas then dried over anhydrous sodium sulfate
  5. customThe solvent was then removed by evaporation under the reduced pressure
  6. customThe crude product thus obtained
  7. customwas purified on Wako Gel
  8. wash(10 ml; elution solvent=n-hexane-ethyl acetate (10:1))

Sources & evidence

ORD record
ord-e5a9f6e56ef940e1b5a26b5427f0fde1
Source dataset
uspto-grants-2006_04
Patent number
US07022855B2

Reaction notes

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