Ammonium Chloride → HCID 60701687, compound

HRID 1747492Notes

Reaction equation

HRID 1747492 reaction equation
CC(C)([O-])C.[Na+].C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[NH:53]1[CH2:58][CH2:57][CH:56]([C:59]([O:61][CH2:62][CH3:63])=[O:60])[CH2:55][CH2:54]1.Br[C:65]1[C:70]([Cl:71])=[CH:69][CH:68]=[CH:67][N:66]=1.[Cl-].[NH4+]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Cl:71][C:70]1[C:65]([N:53]2[CH2:58][CH2:57][CH:56]([C:59]([O:61][CH2:62][CH3:63])=[O:60])[CH2:55][CH2:54]2)=[N:66][CH:67]=[CH:68][CH:69]=1

Participants

8

Reactant 5

HCID 25517Ammonium ChlorideHCID 70770Ethyl 4-piperidinecarboxylateHCID 634876Binap, (A+-)-HCID 70163262-Bromo-3-chloropyridineHCID 23676156Sodium t-butoxide

Product 1

HCID 60701687HCID 60701687, compoundYield 39%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Procedure

Sodium tert-butoxide (0.936 g, 9.74 mmol), 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (0.364 g, 0.585 mmol), and tris(dibenzylideneacetone)dipalladium(0) (0.178 g, 0.195 mmol) were added to a solution of ethyl piperidine-4-carboxylate (2.45 g, 15.6 mmol) and 2-bromo-3-chloropyridine (1.50 g, 7.79 mmol) in toluene (30 mL) under a nitrogen atmosphere, and the mixture was stirred for 4 hours under heating to reflux. A saturated ammonium chloride aqueous solution was added to the reaction solution, followed by extraction with ethyl acetate twice. The obtained organic layer was washed with brine and then dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography [elute: hexane/ethyl acetate=90/10] to obtain the title compound (0.813 g, yield: 39%).

Workup

  1. temperatureunder heating to reflux
  2. extractionfollowed by extraction with ethyl acetate twice
  3. washThe obtained organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography [elute: hexane/ethyl acetate=90/10]

Sources & evidence

ORD record
ord-6131b781e7c64440bc1dc73787f9ed08
Source dataset
uspto-grants-2015_10
Patent number
US09150575B2

Reaction notes

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