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With potassium carbonate In N,N-dimethyl-formamide at 20℃;
Add 1H-pyrazole-3-carbaldehyde (4.02 g, 41.8 mmol) to a 100 mL two-necked flask.Potassium carbonate (11.5 g, 83.2 mmol) and N,N-dimethylformamide (35 mL),Methyl iodide (3.89 mL, 62.5 mmol) was then added and stirred at room temperature overnight.Add water, extract with ethyl acetate (40 mL×6),The organic phase was washed with water (80 mL) and brine (EtOAc)Filter by suction, spin dry, and the residue was purified by silica gel column chromatography(petroleum ether/ethyl acetate (v/v) = 10/1),A pale yellow oil (2.37 g, 51.4percent) was obtained.
Reference：
[1] Patent: CN108690016, 2018, A, . Location in patent: Paragraph 0420; 0422; 0423
With copper(l) iodide; 8-Hydroxyquinoline-N-oxide; caesium carbonate; In dimethyl sulfoxide; at 90℃; for 48h;Inert atmosphere;
A flask was charged with CuI (79 mg, 0.42 mmol), 8-hydroxyquinoline-N-oxide (134 mg, 0.83 mmol), Cs2CO3 (2.713 g, 8.33 mmol), 1H-pyrazole-3-carbaldehyde 42 (400 mg, 4.16 mmol). The flask was evacuated and backfilled with argon. Iodobenzene (0.70 mL, 6.24 mmol) and DMSO (5 mL) were added to the flask under argon atmosphere. After stirring at 90 C for 48 h, the mixture was diluted with water, and extracted with ethyl acetate (3 x 30 mL). The combined organic phases were washed with brine, dried with Na2SO4, filtered, concentrated and purified by silica gel chromatography to afford 68b as a pale yellow solid (329 mg, 46 %).
1-(3-chloro-4-fluorobenzyl)-1H-pyrazole-3-carbaldehyde[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
43%
With potassium carbonate; In acetonitrile; at 20℃;
General procedure: A mixture of 1H-imidazole-2-carbaldehyde 40 (200 mg, 2.08 mmol), potassium carbonate (0.8630 g, 6.24 mmol) and 3-(bromomethyl)-1,1'-biphenyl 38 (0.7716 g, 3.12 mmol) in acetonitrile (10 mL) was stirred overnight at room temperature, then the solvent was removed, diluted with water, and extracted with ethyl acetate (3 x 30 mL). The combined organic phases were washed with brine, dried with Na2SO4, filtered, concentrated and purified by silica gel chromatography to afford 44 as a pale yellow solid (527 mg, 97%).
1-([1,1'-biphenyl]-3-ylmethyl)-1H-pyrazole-3-carbaldehyde[ No CAS ]
1-([1,1'-biphenyl]-3-ylmethyl)-1H-pyrazole-5-carbaldehyde[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
63%; 17%
With potassium carbonate; In acetonitrile; at 20℃;
General procedure: A mixture of 1H-imidazole-2-carbaldehyde 40 (200 mg, 2.08 mmol), potassium carbonate (0.8630 g, 6.24 mmol) and <strong>[14704-31-5]3-(bromomethyl)-1,1'-biphenyl</strong> 38 (0.7716 g, 3.12 mmol) in acetonitrile (10 mL) was stirred overnight at room temperature, then the solvent was removed, diluted with water, and extracted with ethyl acetate (3 x 30 mL). The combined organic phases were washed with brine, dried with Na2SO4, filtered, concentrated and purified by silica gel chromatography to afford 44 as a pale yellow solid (527 mg, 97%).
With potassium carbonate; In N,N-dimethyl-formamide; at 20℃;
Add 1H-pyrazole-3-carbaldehyde (4.02 g, 41.8 mmol) to a 100 mL two-necked flask.Potassium carbonate (11.5 g, 83.2 mmol) and N,N-dimethylformamide (35 mL),Methyl iodide (3.89 mL, 62.5 mmol) was then added and stirred at room temperature overnight.Add water, extract with ethyl acetate (40 mL×6),The organic phase was washed with water (80 mL) and brine (EtOAc)Filter by suction, spin dry, and the residue was purified by silica gel column chromatography(petroleum ether/ethyl acetate (v/v) = 10/1),A pale yellow oil (2.37 g, 51.4percent) was obtained.
ethyl (2Z)-3-(1H-pyrazol-5-yl)prop-2-enoate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
500 mg
With sodium hydride; In tetrahydrofuran; at 20℃; for 2h;
A mixture of ethyl 2-[bis(2,2,2-trifluoroethoxy)phosphoryl]acetate (3.04 g, 9.15 mmol), sodium hydride (400 mg, 16.66 mmol), 1H-pyrazole-5-carbaldehyde (800 mg, 8.32 mmol) in tetrahydrofuran (100 mL) was stirred for 2 h at room temperature. The reaction was quenched with water. The resulting mixture was extracted with ethyl acetate and the organic layers combined and concentrated under vacuum. The residue was purified by flash chromatography on a silica gel column eluted with ethyl acetate/petroleum ether (1/3) to afford ethyl (2Z)-3-(1H-pyrazol-5-yl)prop-2-enoate (500 mg, 2.99 mmol) as a white solid. LCMS (ESI) [M+H]+=167.
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