Potassium Carbonate → tert-butyl 4-pyridin-4-yl-3,6-dihydro-2H-pyridine-1-carboxylate

HRID 551794Notes

Reaction equation

HRID 551794 reaction equation
FC(F)(F)S(O[C:7]1[CH2:8][CH2:9][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:11][CH:12]=1)(=O)=O.[Cl-].[Li+].C(=O)([O-])[O-].[K+].[K+].CC1(C)C(C)(C)OB([C:38]2[CH:43]=[CH:42][N:41]=[CH:40][CH:39]=2)O1>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.O.COCCOC>[N:10]1([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:11][CH:12]=[C:7]([C:38]2[CH:43]=[CH:42][N:41]=[CH:40][CH:39]=2)[CH2:8][CH2:9]1

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 433294Lithium ChlorideHCID 27346484-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridineHCID 10991161Tert-butyl 4-(trifluoromethanesulfonyloxy)-1,2,3,6-tetrahydropyridine-1-carboxylate

Product 1

HCID 67191026tert-butyl 4-pyridin-4-yl-3,6-dihydro-2H-pyridine-1-carboxylateYield 104.5%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

1 g of tert-butyl 4-{[(trifluoromethyl)sulfonyl]oxy}-3,6-dihydropyridine-1(2H)-carboxylate, 0.256 g of lithium chloride, 1.418 g of potassium carbonate, 1.05 g of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine and 0.209 g of tetrakis(triphenylphosphine)palladium are introduced into 15 ml of 1,2-dimethoxyethane in a 100 ml three-necked flask under nitrogen; the mixture is brought to reflux for 1 h 30. The mixture is allowed to return to ambient temperature, 100 ml of water are added and the aqueous phase is extracted with 3 times 80 ml of ethyl acetate. The organic phases are combined and dried over sodium sulfate and the solvent is evaporated under reduced pressure. The residue is chromatographed on silica gel with a dichloromethane to dichloromethane/methanol/aqueous ammonia 90/10/1 elution gradient. 0.821 g of tert-butyl 3,6-dihydro-4,4′-bipyridine-1(2H)-carboxylate is obtained.

Workup

  1. temperatureto reflux for 1 h 30
  2. customto return to ambient temperature
  3. extractionthe aqueous phase is extracted with 3 times 80 ml of ethyl acetate
  4. dry with materialdried over sodium sulfate
  5. customthe solvent is evaporated under reduced pressure
  6. customThe residue is chromatographed on silica gel with a dichloromethane to dichloromethane/methanol/aqueous ammonia 90/10/1 elution gradient

Sources & evidence

ORD record
ord-ecbd15a266ed417a9a7451f6a4811a09
Source dataset
uspto-grants-2011_05
Patent number
US07947834B2

Reaction notes

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