* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
General procedure: To a stirred solution of arylidenemalonate 4 (0.5 mmol) and a -diazo- b -ketosulfone 2 (143 mg, 0.6 mmol, 1.2 equiv) in dry EtOH(5 mL) was added Cs2CO3 (245 mg, 0.75 mmol, 1.5 equiv) at 0C andthe resulting mixture was stirred until the reaction was complete(monitored by TLC). Then the reaction mixture was concentrated invacuo and the crude residue was directly subjected to silica gel column chromatography (pet ether/ethyl acetate: 8/2) to affordpure pyrazole carboxylate 5.
18%
With ethanol; sodium ethanolate; for 5.0h;
General procedure: To a stirred solution of arylidenemalonate 4 (0.5 mmol) and a -diazo- b -ketosulfone 2 (143 mg, 0.6 mmol, 1.2 equiv) in dry EtOH(5 mL) was added Cs2CO3 (245 mg, 0.75 mmol, 1.5 equiv) at 0C andthe resulting mixture was stirred until the reaction was complete(monitored by TLC). Then the reaction mixture was concentrated invacuo and the crude residue was directly subjected to silica gel column chromatography (pet ether/ethyl acetate: 8/2) to affordpure pyrazole carboxylate 5.
General procedure: To a stirred solution of arylidenemalonate 4 (0.5 mmol) and a -diazo- b -ketosulfone 2 (143 mg, 0.6 mmol, 1.2 equiv) in dry EtOH(5 mL) was added Cs2CO3 (245 mg, 0.75 mmol, 1.5 equiv) at 0C andthe resulting mixture was stirred until the reaction was complete(monitored by TLC). Then the reaction mixture was concentrated invacuo and the crude residue was directly subjected to silica gel column chromatography (pet ether/ethyl acetate: 8/2) to affordpure pyrazole carboxylate 5.
General procedure: To a stirred solution of 7 (0.5mmol, 1 equiv) and alpha-diazo-beta-ketosulfone 2 (143mg, 0.6mmol, 1.2 equiv) in dry EtOH (5mL) was added NaOEt (51mg, 0.75mmol, 1.5 equiv) at 0C and the resulting mixture was stirred at the same temperature until the reaction was complete (monitored by TLC). Then the reaction mixture was concentrated in vacuo and the crude residue was directly subjected to silica gel column chromatography (pet ether/ethyl acetate: 8/2) to afford pure 3, 5 or 8.
With ethanol; caesium carbonate; at 80.0℃; for 0.25h;Microwave irradiation;
General procedure: In a 10mL microwave glass vial containing EtOH (1mL), was added pyrazoline 6 (0.1mmol) followed by Cs2CO3 (16.5mg, 0.05mmol, 0.5 equiv) and the resulting mixture was subjected to microwave irradiation for 10-15minat 80C until the completion of reaction (monitored by TLC). After removal of EtOH in vacuo, the residue was treated with water (10mL) and the aqueous layer was extracted with EtOAc (2×10mL). The combined organic layer was dried over anhydrous Na2SO4, filtered and the filtrate was then concentrated in vacuo. The residue was recrystallized from EtOAc/hexane (1:1) to obtain pure 5 in quantitative yields.
Chemistry
Pharmaceutical Intermediates
Inhibitors/Agonists
Material Science
For Research Only
120K+ Compounds
Competitive Price
1-2 Day Shipping
