N-methoxy-N-methyl-6-(trifluoromethyl)nicotinamide → Cyclopropyl(6-(trifluoromethyl)pyridin-3-yl)methanone
Reaction equation
CON(C)[C:4](=[O:15])[C:5]1[CH:10]=[CH:9][C:8]([C:11]([F:14])([F:13])[F:12])=[N:7][CH:6]=1.[CH:17]1([Mg]Br)[CH2:19][CH2:18]1>O1CCCC1>[CH:17]1([C:4]([C:5]2[CH:6]=[N:7][C:8]([C:11]([F:14])([F:13])[F:12])=[CH:9][CH:10]=2)=[O:15])[CH2:19][CH2:18]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a stirred solution of N-methoxy-N-methyl-6-(trifluoromethyl)nicotinamide (1.00 g, 4.27 mmol) in tetrahydrofuran (30 mL) at 0° C. was added 0.5 M of cyclopropylmagnesium bromide in tetrahydrofuran (20 mL, 0.01 mol) dropwise over 15 minutes. The mixture was stirred at 0° C. for 30 minutes then at room temperature overnight. The reaction was quenched with 1N HCl. Solvent was pumped off and the water layer was extracted with ethyl acetate. Organics were combined and dried with MgSO4, filtered and concentrated to obtain a crude brown oil. The crude product was purified by silica gel column (0-60% ethyl acetate/hexane) to obtain a pale yellow solid.
Workup
- customat room temperature
- customovernight
- customThe reaction was quenched with 1N HCl
- extractionthe water layer was extracted with ethyl acetate
- dry with materialdried with MgSO4
- filtrationfiltered
- concentrationconcentrated
- customto obtain a crude brown oil
- customThe crude product was purified by silica gel column (0-60% ethyl acetate/hexane)
- customto obtain a pale yellow solid
Sources & evidence
- ORD record
- ord-7c363eecaf3b4112bf45cc8b956101bd
- Source dataset
- uspto-grants-2014_02
- Patent number
- US08653091B2
Reaction notes
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