Ammonium Chloride → HCID 29997195, compound

HRID 1747494Notes

Reaction equation

HRID 1747494 reaction equation
CC(C)([O-])C.[Na+].C1(P(C2C=CC=CC=2)C2(P(C3C=CC=CC=3)C3C=CC=CC=3)CC=C3C(C=CC=C3)=C2C2C3C(=CC=CC=3)C=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[CH:70]=[CH:69][C:68]([Cl:71])=[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:68]1[CH:69]=[CH:70][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]=1

Participants

8

Reactant 5

HCID 25517Ammonium ChlorideHCID 70770Ethyl 4-piperidinecarboxylateHCID 8170982-Bromo-5-chloropyridineHCID 23676156Sodium t-butoxideHCID 86595863(+/-)-2,2-Bis(diphenylphosphino)-1,1-binaphthyl

Product 1

HCID 29997195HCID 29997195, compoundYield 53%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Procedure

Sodium t-butoxide (1.25 g, 13.0 mmol), 2,2-bis(diphenylphosphino)-1,1-binaphthyl (0.485 g, 0.779 mmol), and tris(dibenzylideneacetone)dipalladium(0) (0.238 g, 0.260 mmol) were added to a solution of ethyl piperidine-4-carboxylate (2.00 g, 10.4 mmol) and 2-bromo-5-chloropyridine (2.00 g, 10.4 mmol) in toluene (50 mL), and the mixture was stirred for 1 hour under heating to reflux. A saturated ammonium chloride aqueous solution was added to the reaction solution, followed by extraction with toluene 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=85/15] to obtain the title compound (1.47 g, yield: 53%).

Workup

  1. temperatureunder heating to reflux
  2. extractionfollowed by extraction with toluene 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=85/15]

Sources & evidence

ORD record
ord-97c87c3deac449828209adf81c271355
Source dataset
uspto-grants-2015_10
Patent number
US09150575B2

Reaction notes

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