Cesium carbonate → α-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-1-propanenitrile
Reaction equation
[CH3:1][C:2]1([CH3:14])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:10]=[N:11][NH:12][CH:13]=2)[O:3]1.Cl[CH2:16][CH:17]([CH3:20])[C:18]#[N:19].C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C.C(OCC)(=O)C>[CH3:16][CH:17]([CH2:20][N:12]1[CH:13]=[C:9]([B:4]2[O:5][C:6]([CH3:7])([CH3:8])[C:2]([CH3:14])([CH3:1])[O:3]2)[CH:10]=[N:11]1)[C:18]#[N:19]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 90 °C
Procedure
A mixture of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (0.050 g, 0.26 mmol), 3-chloro-2-methylpropanenitrile (27 uL, 0.28 mmol, Aldrich, Cat. No. 150428), and cesium carbonate (250 mg, 0.77 mmol) in acetonitrile (1 mL) in a sealed reaction vial was stirred at 90° C. overnight. After cooling it was diluted with ethyl acetate. Then the organic solution was washed with water, brine; dried over Na2SO4. After filtration the filtrate was concentrated to yield 41 mg product. It was directly used in the next step reaction without further purification.
Workup
- temperatureAfter cooling it
- washThen the organic solution was washed with water, brine
- dry with materialdried over Na2SO4
- filtrationAfter filtration the filtrate
- concentrationwas concentrated
Sources & evidence
- ORD record
- ord-ad33869175594f99b53718c43e140a58
- Source dataset
- uspto-grants-2013_05
- Patent number
- US08436008B2
Reaction notes
Loading…