Reaction equation
[CH2:1]([O:3][CH:4]([N:6]1[CH:10]=[C:9](I)[CH:8]=[N:7]1)[CH3:5])[CH3:2].[CH:12]([C:14]1[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][CH:15]=1)=[CH2:13].[Br-].C([O-])(=O)C.C(=O)([O-])[O-].[K+].[K+]>>[CH2:1]([O:3][CH:4]([N:6]1[CH:10]=[C:9](/[CH:13]=[CH:12]/[C:14]2[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][CH:15]=2)[CH:8]=[N:7]1)[CH3:5])[CH3:2]Participants
Procedure
1-(1-Ethoxyethyl)-4-iodo-1H-pyrazole obtained in Step 1 (162.0 mg) was suspended in N,N-methylformamide (5.0 mL), and added thereto were 4-vinylbenzonitrile (157.3 mg), tetrabutylamonuim bromide (19.6 mg), paladium acetate (41.0 mg) and potassium carbonate (210.4 mg). The mixture was stirred at room temperature for 10 minutes, and subjected to microwave irradiation at 140° C. for 20 minutes. After completion of the reaction, the resulting mixture was filtered through silica gel, and extracted with ethyl acetate (15 mL). The extract was washed successively with saturated ammonium chloride (15 mL) and brine (15 mL). The organic layer was dried over anhydrous magnesium sulfate and concentrated by evaporation under a reduced pressure. The resulting residue was purified by silica gel chromatography to obtain the title compound (0.11 g, yield 61%).
Workup
- additionadded
- customirradiation at 140° C. for 20 minutes
- customAfter completion of the reaction
- filtrationthe resulting mixture was filtered through silica gel
- extractionextracted with ethyl acetate (15 mL)
- washThe extract was washed successively with saturated ammonium chloride (15 mL) and brine (15 mL)
- dry with materialThe organic layer was dried over anhydrous magnesium sulfate
- concentrationconcentrated by evaporation under a reduced pressure
- customThe resulting residue was purified by silica gel chromatography
Sources & evidence
- ORD record
- ord-580cdbf9bae14f57b9f252631e345925
- Source dataset
- uspto-grants-2011_11
- Patent number
- US08063229B2
Linked notes
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