HCID 118497062, compound → HCID 118497167, compound

HRID 522139Notes

Reaction equation

HRID 522139 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([CH:18]=[C:19]([F:21])[F:20])[N:13]=2)=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[H][H]>CCOC(C)=O.[Pd]>[Cl:1][C:2]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([CH2:18][CH:19]([F:21])[F:20])[N:13]=2)=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

5

Reactant 2

HCID 118497062HCID 118497062, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 118497167HCID 118497167, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of methyl 2-chloro-5-(6-(2,2-difluorovinyl)pyridin-2-yl)benzoate (Preparation 33, 105 mg, 0.34 mmol) in EtOAc (1 mL) was added 10% palladium on alumina (36 mg, 0.03 mmol) and stirred at room temperature under 15 psi of hydrogen for 2 hours. The reaction was filtered and concentrated in vacuo. The residue was purified using silica gel column chromatography eluting with 0-20% EtOAc in heptanes to afford the title compound.

Workup

  1. filtrationThe reaction was filtered
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified
  4. washeluting with 0-20% EtOAc in heptanes

Sources & evidence

ORD record
ord-31abde045d764466b5d7519ddca7b1ab
Source dataset
uspto-grants-2016_05
Patent number
US09328096B2

Reaction notes

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