Reacción #162477

Ecuación de reacción

(S)-tert-butyl (1-(6-bromo-1-methyl-1H-pyrrolo[3,2-b]pyridin-5-yl)ethyl)carbamate

3,5-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

potassium carbonate

→

title compound

tert-Butyl ((1S)-1-(6-(3,5-dimethyl-1H-pyrazol-4-yl)-1-methyl-1H-pyrrolo[3,2-b]pyridin-5-yl)ethyl)carbamate

Disolventes

dioxane

ethyl acetate

Condiciones de reacción

Tratamiento posterior

1. 1
   Lavadowashed with saturated ammonium chloride (177 mL) and brine
2. 2
   Secadodried over Na2SO4
3. 3
   Concentraciónconcentrated in vacuo
4. 4
   OtroThe crude product was purified on silica gel
5. 5
   Lavadoeluting with EtOAc

Procedimiento

A solution of (S)-tert-butyl (1-(6-bromo-1-methyl-1H-pyrrolo[3,2-b]pyridin-5-yl)ethyl)carbamate (2 g, 5.65 mmol), 3,5-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (1160 mg, 5.20 mmol) and PdCl2(dppf)-CH2Cl2 adduct (147 mg, 0.180 mmol) in dioxane (3500 μL) and aqueous 3M potassium carbonate solution (5400 μL, 16 mmol) was heated at 120° C. for 5 hours in a microwave reactor. The mixture was diluted with ethyl acetate (177 mL), washed with saturated ammonium chloride (177 mL) and brine, dried over Na2SO4, and concentrated in vacuo. The crude product was purified on silica gel, eluting with EtOAc to give the title compound. ESI-MS m/z [M+H]+ calc'd for C20H27N5O2, 370.2. found 370.6.

Fuente