Sodium Bicarbonate → 1-[6-(Trifluoromethyl)pyridin-3-yl]ethan-1-one

HRID 241446Notes

Reaction equation

HRID 241446 reaction equation
CON(C)[C:4]([C:6]1[CH:7]=[N:8][C:9]([C:12]([F:15])([F:14])[F:13])=[CH:10][CH:11]=1)=[O:5].[CH3:17][Mg]Br.C([O-])(O)=O.[Na+]>C1COCC1>[F:13][C:12]([F:15])([F:14])[C:9]1[N:8]=[CH:7][C:6]([C:4](=[O:5])[CH3:17])=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 23116945N-methoxy-N-methyl-6-(trifluoromethyl)nicotinamideHCID 178418573HCID 178418573, compound

Product 1

HCID 218805781-[6-(Trifluoromethyl)pyridin-3-yl]ethan-1-oneYield 98.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Dissolve N-methoxy-N-methyl-6-(trifluoromethyl)pyridine-3-carboxamide (0.685 g, 2.92 mmol) in THF (20 mL). Add methylmagnesium bromide (3.0 M in EtO2, 1.950 mL, 5.850 mmol). Stir the mixture for 16 hours. Pour the reaction mixture into a saturated NaHCO3 aqueous solution (20 mL). Extract with EtOAc (3×20 mL). Wash the combined organic extracts with water (30 mL) and saturated sodium chloride (2×30 mL). Dry the organic extracts over sodium sulfate; filter; collect the filtrate; and concentrate the filtrate under reduced pressure to give the title compound (0.545 g, 98%) as a light yellow solid. 1H NMR (400.43 MHz, d6-DMSO) δ 9.21-9.21 (m, 1H), 8.51-8.49 (m, 1H), 8.03 (d, J=8.2 Hz, 1H), 2.64 (s, 3H).

Workup

  1. extractionExtract with EtOAc (3×20 mL)
  2. washWash the combined organic extracts with water (30 mL) and saturated sodium chloride (2×30 mL)
  3. dry with materialDry the organic extracts over sodium sulfate
  4. filtrationfilter
  5. customcollect the filtrate
  6. concentrationand concentrate the filtrate under reduced pressure

Sources & evidence

ORD record
ord-c7c062fb817a4607920c2d0dccfb3fa1
Source dataset
uspto-grants-2014_02
Patent number
US08648200B2

Reaction notes

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