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butyl (E)-3-(1-methyl-5-nitro-1H-indazol-3-yl)acrylate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
90%
With tetrabutylammomium bromide; palladium diacetate; triethylamine; triphenylphosphine; sodium bromide; In neat (no solvent); for 2.5h;Milling;
General procedure: A mixture of the substrate 1 (1.5 mmol), alkene 2 (2.25 mmol), Pd(OAc)2 (0.075 mmol), PPh3 (0.15 mmol), TEA (1.8 mmol), TBAB (0.075 mmol), and NaBr (10.0 g) was placed in a stainless-steel vessel, along with 207 stainless-steel balls (dMB = 6 mm, MB = 0.293). The reaction mixture was then ball-milled at 800 rpm for 90 min. At the end of the experiment, the reaction mixture was scratched off from the vessel and directly purified by column chromatography on silica gel (petroleum ether/EtOAc) to give the desired product 3.
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate; In 1,4-dioxane; water; at 100.0℃; for 3.0h;Inert atmosphere;
Compound 1 (2.0 g, 7.8 mmol, 1 eq), PB03145 (2.89 g, 9.36 mmol, 1.2 eq)Pd(dppf)Cl2 (570 mg, 0.78 mmol, 0.1 eq),Potassium phosphate (4.97 g, 23.4 mmol, 3 eq) was added to a 100 ml single-mouth bottle.Add dioxane (10 ml), water (2 ml), and replace with nitrogen three times.The temperature was raised to 100 ° C, and the reaction was carried out for 3 hours, and the reaction was terminated by TLC.The reaction solution was cooled to room temperature and EA (100 mL) was added.Water (30 ml), the organic phase was separated and washed with saturated brine (50 ml).The organic phase was dried over magnesium sulfate and dried.Add n-heptane (100 ml) and filter to give a yellow solid (2.3 g crude).
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