Reacción #1140299

Ecuación de reacción

5-bromo-3-(1-isopropyl-1H-[1,2,3]triazol-4-yl)-pyridin-2-ylamine

(3-methoxy-4-(methoxycarbonyl)phenyl)boronic acid

water

Cs2CO3

→

title compound

Rendimiento 69.4%

4-(6-amino-5-(1-isopropyl-1H-1,2,3-triazol-4-yl)pyridin-3-yl)-2-methoxybenzoic acid

Rendimiento 69.4%

Disolventes

1,4-dioxane

EtOAc

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe reaction mixture was degassed with argon for 30 min
2. 2
   TemperaturaThe reaction mixture was cooled to RT
3. 3
   Lavadowashed with water (50 mL)
4. 4
   Extracciónextracted with DCM (2×50 mL)
5. 5
   Lavadowashed with brine solution (20 mL)
6. 6
   Secadodried over anhydrous Na2SO4 and solvent
7. 7
   Otrowas evaporated under reduced pressure
8. 8
   LavadoThe crude compound was washed with diethyl ether

Procedimiento

To a solution of 5-bromo-3-(1-isopropyl-1H-[1,2,3]triazol-4-yl)-pyridin-2-ylamine (300 mg, 1.06 mmol) and (3-methoxy-4-(methoxycarbonyl)phenyl)boronic acid (245 mg, 1.16 mmol) in 1,4-dioxane (10.0 mL)/water (5.0 mL) was added Cs2CO3 (1.0 g, 3.18 mmol) at room temperature. The reaction mixture was degassed with argon for 30 min. Then Pd(PPh3)4 (61 mg, 0.05 mmol) was added and allowed to stir at 120° C. for 30 min in CEM micro wave. The reaction mixture was cooled to RT, diluted with EtOAc (50 mL) and washed with water (50 mL). The aqueous layer was neutralized with 1N HCl, extracted with DCM (2×50 mL), washed with brine solution (20 mL), dried over anhydrous Na2SO4 and solvent was evaporated under reduced pressure. The crude compound was washed with diethyl ether to afford 260 mg (yield: 69.33%) of the title compound as pale yellow solid.

Fuente