Dimethylformamide → Methyl 2-cyano-6-phenylisonicotinate

HRID 1096959Notes

Reaction equation

HRID 1096959 reaction equation
[C:1]1([C:7]2[CH:12]=[C:11]([C:13]([O:15][CH3:16])=[O:14])[CH:10]=[C:9](OS(C(F)(F)F)(=O)=O)[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:25][N:26](C=O)C>[C-]#N.[Zn+2].[C-]#N.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>[C:25]([C:9]1[CH:10]=[C:11]([C:13]([O:15][CH3:16])=[O:14])[CH:12]=[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[N:8]=1)#[N:26]

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 57930938Methyl 2-phenyl-6-{[(trifluoromethyl)sulfonyl]oxy}pyridine-4-carboxylate

Product 1

HCID 57930992Methyl 2-cyano-6-phenylisonicotinate

Reagents, catalysts & solvents 2

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
90 °C

Procedure

Zinc cyanide (4 g) and Pd(PPh3)4 (1.16 g) were added to a DMF (60 mL) solution of methyl 2-phenyl-6-{[(trifluoromethyl)sulfonyl]oxy}pyridine-4-carboxylate (3.7 g), and stirred at 90° C. for 3 hours. The reaction liquid was filtered through Celite, the solvent was partly evaporated away, the residue was diluted with ethyl acetate, water was added to it, and the solution was extracted with ethyl acetate. The organic layer was washed with water and saturated saline water, dried with anhydrous sodium sulfate, filtered and the solvent was evaporated away. The residue was purified through silica gel column chromatography (hexane/ethyl acetate) to obtain the title compound as a yellow powder.

Workup

  1. customThe reaction liquid
  2. filtrationwas filtered through Celite
  3. customthe solvent was partly evaporated away
  4. additionthe residue was diluted with ethyl acetate, water
  5. additionwas added to it
  6. extractionthe solution was extracted with ethyl acetate
  7. washThe organic layer was washed with water and saturated saline water
  8. dry with materialdried with anhydrous sodium sulfate
  9. filtrationfiltered
  10. customthe solvent was evaporated away
  11. customThe residue was purified through silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-a40f0d5fe9094a7797ba32cffbf420e7
Source dataset
uspto-grants-2012_03
Patent number
US08138197B2

Reaction notes

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