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 μL, 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 removed and the aqueous layer was extracted with ethyl acetate. Thr organic layers were combined and dried with MgSO4, filtered and concentrated. 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
- customSolvent was removed
- extractionthe aqueous layer was extracted with ethyl acetate
- dry with materialdried with MgSO4
- filtrationfiltered
- concentrationconcentrated
- 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-5ae7d0d1f3534e829a3de6b3c62bbd8a
- Source dataset
- uspto-grants-2011_12
- Patent number
- US08076345B2
Reaction notes
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