4-bromo-N-methoxy-N,1-dimethyl-1H-pyrazole-3-carboxamide → (4-bromo-1-methyl-1H-pyrazol-3-yl)(4-chlorophenyl)methanone
Reaction equation
[Br:1][C:2]1[C:3]([C:8](N(OC)C)=[O:9])=[N:4][N:5]([CH3:7])[CH:6]=1.[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([Mg]Br)=[CH:17][CH:16]=1>O1CCCC1>[Br:1][C:2]1[C:3]([C:8]([C:18]2[CH:19]=[CH:20][C:15]([Cl:14])=[CH:16][CH:17]=2)=[O:9])=[N:4][N:5]([CH3:7])[CH:6]=1Participants
Procedure
To a solution of compound 4-bromo-N-methoxy-N,1-dimethyl-1H-pyrazole-3-carboxamide (1.0 g, 4 mmol) in anhydrous tetrahydrofuran (20 mL) under nitrogen atmosphere was added (4-chlorophenyl)magnesium bromide (8 mL) in tetrahydrofuran (1 M) at 0° C., The resulting mixture was stirred for 2 h at room temperature. The reaction was quenched by saturated solution of ammonium chloride, and dichloromethane (100 mL) was added, the separated organic layer was dried over anhydrous sodium sulfate and concentrated in vacuum. The residue was purified by flash chromatography eluting with petroleum ether/ethyl acetate=5:1 to give the titled product as a white solid (1.0 g, 84%). LC/MS m/z 298 [M+H]+; 1H NMR (300 MHz, CDCl3) δ 8.10 (d, J=9 Hz, 2H), 7.53 (s, 1H), 7.43 (d, J=9 Hz, 2H), 3.99 (s, 3H).
Workup
- customThe reaction was quenched by saturated solution of ammonium chloride, and dichloromethane (100 mL)
- additionwas added
- dry with materialthe separated organic layer was dried over anhydrous sodium sulfate
- concentrationconcentrated in vacuum
- customThe residue was purified by flash chromatography
- washeluting with petroleum ether/ethyl acetate=5:1
Sources & evidence
- ORD record
- ord-c71cac47280541ba980084ca1daa03fb
- Source dataset
- uspto-grants-2014_08
- Patent number
- US08796261B2
Reaction notes
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