Isopropyl iodide → 1-Isopropyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole
Reaction equation
[CH3:1][C:2]1([CH3:14])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:13]=[CH:12][NH:11][N:10]=2)[O:3]1.[H-].[Na+].I[CH:18]([CH3:20])[CH3:19]>CN(C)C=O.O>[CH:18]([N:11]1[CH:12]=[CH:13][C:9]([B:4]2[O:5][C:6]([CH3:7])([CH3:8])[C:2]([CH3:14])([CH3:1])[O:3]2)=[N:10]1)([CH3:20])[CH3:19]Participants
6
Procedure
3-(4,4,5,5-Tetramethyl[1,3,2]dioxaborolan-2-yl)-1H-pyrazole (0.52 g) was added to a stirred suspension of sodium hydride (60% in oil, 0.096 g) in N,N-dimethylformamide (18 mL) at 0° C., and the resulting mixture was stirred at room temperature for 1 hour. The mixture was then cooled to 0° C., treated with 2-iodopropane (0.4 mL) and stirred at room temperature for 16 hours. The mixture was diluted with water (10 mL) and concentrated to low bulk under reduced pressure. The residue was extracted with ethyl acetate, and the combined extracts were washed with saturated aqueous sodium chloride solution and then dried over magnesium sulfate. The solvent was removed under reduced pressure to afford title compound (0.152 g).
Workup
- temperatureThe mixture was then cooled to 0° C.
- stirringstirred at room temperature for 16 hours
- concentrationconcentrated to low bulk under reduced pressure
- extractionThe residue was extracted with ethyl acetate
- washthe combined extracts were washed with saturated aqueous sodium chloride solution
- dry with materialdried over magnesium sulfate
- customThe solvent was removed under reduced pressure
Sources & evidence
- ORD record
- ord-bec44e242b914ee290b02d8365b60144
- Source dataset
- uspto-grants-2013_03
- Patent number
- US08394830B2
Reaction notes
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