Pyridine → HCID 70372059, compound

HRID 1074313Notes

Reaction equation

HRID 1074313 reaction equation
N1C=CC=CC=1.[CH3:7][S:8]([C:11]1[CH:16]=[CH:15][C:14]([C:17]#[C:18][CH2:19][F:20])=[CH:13][CH:12]=1)(=[O:10])=[O:9].[H][H]>[Pd].CC([O-])=O.CC([O-])=O.[Pb+2].C(OCC)(=O)C.[Pd]>[CH3:7][S:8]([C:11]1[CH:16]=[CH:15][C:14]([CH2:17]/[CH:18]=[CH:19]\[F:20])=[CH:13][CH:12]=1)(=[O:10])=[O:9]

Participants

7

Reactant 3

HCID 1049Pyridine2×HCID 13590075HCID 13590075, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 70372059HCID 70372059, compoundYield 99.3%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 131709914Lindlars catalystCatalyst2×HCID 8857Ethyl AcetateSolvent

Procedure

cis-hydrogenation using Lindlar catalyst and pyridine: Stir a mixture of 533 mg, 2.51 mmoles of the title compound of Example 1 (recrystallized from dichloromethane-hexane), 211 mg, 2.67 mmoles of pyridine and 127 mg of Lindlar catalyst (palladium on calcium carbonate, poisoned with lead (obtained from Aldrich) in 25 mL of ethyl acetate under hydrogen at atomospheric pressure at 26° C. for 1 hr until the theoretical amount of hydrogen (62 mL) is consumed. Remove the catalyst by filtration and wash it with ethyl acetate. Wash the ethyl acetate solution successively with ice-cold 4% HCl solution, saturated NaHCO3 solution and water, and dry over anhydrous MgSO4. Evaporate solvent under vacuum to give the title compound as an oil (534 mg).

Workup

  1. customis consumed
  2. customRemove the catalyst
  3. filtrationby filtration
  4. washwash it with ethyl acetate
  5. washWash the ethyl acetate solution successively with ice-cold 4% HCl solution, saturated NaHCO3 solution and water
  6. dry with materialdry over anhydrous MgSO4

Sources & evidence

ORD record
ord-0bff7090d48d4070adf006504660b498
Source dataset
uspto-grants-1990_11
Patent number
US04973750

Reaction notes

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