Reacción #1142818

Ecuación de reacción

compound

1-(2,2-Diethoxyethyl)-1′-(4-methoxybenzyl)-1H,1′H-3,4′-bipyrazol-5-amine

2-bromo-4-nitrotoluene

caesium carbonate

xantphos

→

1-(2,2-Diethoxyethyl)-1′-(4-methoxybenzyl)-N-(2-methyl-5-nitrophenyl)-1H,1′H-3,4′-bipyrazole-5-amine

Disolventes

1,4-dioxane

Condiciones de reacción

Tratamiento posterior

1. 1
   Filtraciónfiltered through kieselguhr
2. 2
   Concentraciónthe filtrate was concentrated on a rotary evaporator
3. 3
   Lavadowashed with semiconcentrated sodium bicarbonate solution
4. 4
   SecadoThe organic phase was dried over anhydrous sodium sulphate
5. 5
   Concentraciónconcentrated
6. 6
   OtroThe crude product was purified chromatographically (Method 26)

Procedimiento

Under argon, a mixture of the compound from Example 2A (2.9 g, 7.5 mmol), 2-bromo-4-nitrotoluene (2.11 g, 9.78 mmol), palladium(II) acetate (0.17 g, 0.75 mmol), caesium carbonate (4.90 g, 15.1 mmol) and xantphos (4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; 0.44 g, 0.75 mmol) in 37 ml of 1,4-dioxane was divided into several 20 ml-microwave reactor vessels. Each batch was heated in a single-mode microwave reactor (Biotage Emrys Optimizer) at 150° C. for 30 min. The batches were subsequently combined and filtered through kieselguhr, and the filtrate was concentrated on a rotary evaporator. The residue was taken up in ethyl acetate and washed with semiconcentrated sodium bicarbonate solution and then with concentrated sodium chloride solution. The organic phase was dried over anhydrous sodium sulphate and concentrated. The crude product was purified chromatographically (Method 26). This gave 2.74 g (70% of theory) of the title compound.

Fuente