Sodium Carbonate → HCID 22615544, compound

HRID 1670755Notes

Reaction equation

HRID 1670755 reaction equation
C(OC([N:8]1[CH2:13][CH:12]=[C:11](OS(C(F)(F)F)(=O)=O)[CH2:10][CH2:9]1)=O)(C)(C)C.[Cl:22][C:23]1[CH:24]=[C:25](OB(O)O)[CH:26]=[CH:27][C:28]=1[F:29].[Cl-].[Li+].C(=O)([O-])[O-].[Na+].[Na+].C(=O)([O-])O.[Na+]>C(COC)OC>[Cl:22][C:23]1[CH:24]=[C:25]([C:11]2[CH2:10][CH2:9][NH:8][CH2:13][CH:12]=2)[CH:26]=[CH:27][C:28]=1[F:29]

Participants

7

Reactant 5

HCID 10340Sodium CarbonateHCID 433294Lithium ChlorideHCID 516892Sodium BicarbonateHCID 10991161Tert-butyl 4-(trifluoromethanesulfonyloxy)-1,2,3,6-tetrahydropyridine-1-carboxylateHCID 18373952HCID 18373952, compound

Product 1

HCID 22615544HCID 22615544, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

4-{[(Trifluoromethyl)sulfonyl]oxy}-3,6-dihydropyridine-1(2H)carboxylic acid tert-butyl ester (synthesized according to the method described in Synthesis, 1991, 993-995, 1.0 g), 3-chloro-4-fluorophenylboric acid (Aldrich Co., 790 mg), lithium chloride (380 mg), tetrakistriphenylphosphine palladium (170 mg) and a 2N sodium carbonate aqueous solution (5 ml) were added to dimethoxyethane (12 ml), and the mixture was heated under reflux for 6 hr. After completion of the reaction, the reaction mixture was washed with a sodium carbonate aqueous solution and aqueous ammonia, and the aqueous layer was extracted with ethyl acetate. The organic layers were combined and dried, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (elution solvent: hexane-ethyl acetate (20:1-10:1)). The intermediate was dissolved in methylene chloride, and trifluoroacetic acid was added. The mixture was stirred at room temperature for 8 hr. After completion of the reaction, a saturated aqueous sodium hydrogen carbonate solution was added and the mixture was extracted with chloroform. The organic layer was dried and the solvent was evaporated under reduced pressure. The precipitated solid was collected by filtration to give 4-(3-chloro-4-fluorophenyl)-1,2,3,6-tetrahydropyridine (357 mg, yield 56%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 6 hr
  3. customAfter completion of the reaction
  4. washthe reaction mixture was washed with a sodium carbonate aqueous solution and aqueous ammonia
  5. extractionthe aqueous layer was extracted with ethyl acetate
  6. customdried
  7. customthe solvent was evaporated under reduced pressure
  8. customThe obtained residue was purified by silica gel column chromatography (elution solvent: hexane-ethyl acetate (20:1-10:1))
  9. dissolutionThe intermediate was dissolved in methylene chloride
  10. additiontrifluoroacetic acid was added
  11. customAfter completion of the reaction
  12. extractionthe mixture was extracted with chloroform
  13. customThe organic layer was dried
  14. customthe solvent was evaporated under reduced pressure
  15. filtrationThe precipitated solid was collected by filtration

Sources & evidence

ORD record
ord-560545f7f90641eaa29608fbe4b256fc
Source dataset
uspto-grants-2011_08
Patent number
US07994196B2

Reaction notes

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