Methyl 3-(4-cyano-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-5-yl)-4-methylbenzoate → Methyl 3-(4-cyano-1H-pyrazol-5-yl)-4-methylbenzoate
Reaction equation
[C:1]([C:3]1[CH:4]=[N:5][N:6](COCC[Si](C)(C)C)[C:7]=1[C:8]1[CH:9]=[C:10]([CH:15]=[CH:16][C:17]=1[CH3:18])[C:11]([O:13][CH3:14])=[O:12])#[N:2]>C([SiH](CC)CC)C.FC(F)(F)C(O)=O>[C:1]([C:3]1[CH:4]=[N:5][NH:6][C:7]=1[C:8]1[CH:9]=[C:10]([CH:15]=[CH:16][C:17]=1[CH3:18])[C:11]([O:13][CH3:14])=[O:12])#[N:2]Participants
Procedure
Into a 50-mL round-bottom flask, was placed a solution of methyl 3-(4-cyano-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-5-yl)-4-methylbenzoate (compound 256.3, 1.9 g, 5.11 mmol) in triethylsilane (4 mL) and trifluoroacetic acid (8 mL). The resulting solution was stirred for 4 h at room temperature, then concentrated under reduced pressure. The pH of the residue was carefully adjusted to 7-8 with aqueous sodium bicarbonate (sat.), then the aqueous phase was extracted with ethyl acetate (2×100 mL). The combined organic layers were dried (Na2SO4), filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography with ethyl acetate/petroleum ether (20/1) as eluent to obtain the title compound as a white solid (600 mg, 49%).
Workup
- customInto a 50-mL round-bottom flask, was placed
- concentrationconcentrated under reduced pressure
- extractionthe aqueous phase was extracted with ethyl acetate (2×100 mL)
- dry with materialThe combined organic layers were dried (Na2SO4)
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- customThe residue was purified by silica gel chromatography with ethyl acetate/petroleum ether (20/1) as eluent
Sources & evidence
- ORD record
- ord-0435af20fbde4cfea6b95d7b0debf43c
- Source dataset
- uspto-grants-2016_08
- Patent number
- US09428502B2
Reaction notes
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