N-Methoxy-N-methylpicolinamide → (6-Fluoro-5-trifluoromethyl-cyclohexa-2,4-dienyl)-pyridin-2-yl-methanone

HRID 735459Notes

Reaction equation

HRID 735459 reaction equation
CON(C)[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][N:7]=1)=[O:5].[F:13][C:14]1[C:19]([C:20]([F:23])([F:22])[F:21])=[CH:18][CH:17]=[CH:16][C:15]=1[Mg]Br>C1COCC1.C(OCC)(=O)C.[Cl-].[NH4+]>[F:13][CH:14]1[CH:15]([C:4]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][N:7]=2)=[O:5])[CH:16]=[CH:17][CH:18]=[C:19]1[C:20]([F:21])([F:22])[F:23]

Participants

6

Reactant 2

HCID 11829796N-Methoxy-N-methylpicolinamideHCID 178505972HCID 178505972, compound

Product 1

HCID 67021129(6-Fluoro-5-trifluoromethyl-cyclohexa-2,4-dienyl)-pyridin-2-yl-methanone

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolventHCID 25517Ammonium ChlorideSolvent

Procedure

Then a solution of pyridine-2-carboxylic acid methoxy-methyl-amide (1.5 g, 9 mmoles) was allowed to react with 2-flouro-3-trifluoromethylphenylmagnesium bromide (2.72 g, 10 mmoles) in THF (30 mL) at 60° C. overnight. The reaction mixture was cooled and diluted with ethyl acetate and ammonium chloride. The organic portion was washed with brine and dried over MgSO4 and stripped to afford a crude product, which was purified by chromatography with CH2Cl2 to give (6-fluoro-5-trifluoromethyl-cyclohexa-2,4-dienyl)-pyridin-2-yl-methanone as a colorless liquid (1.6 gr., 65%).

Workup

  1. temperatureThe reaction mixture was cooled
  2. washThe organic portion was washed with brine
  3. dry with materialdried over MgSO4
  4. customto afford a crude product, which
  5. customwas purified by chromatography with CH2Cl2

Sources & evidence

ORD record
ord-c2c1b734b4ae402491f53051d7cbd190
Source dataset
uspto-grants-2009_09
Patent number
US07592363B2

Reaction notes

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