Reacción #679405

Ecuación de reacción

N-(5-(4-acetylpiperazin-1-yl)pyridin-2-yl)-2-(6-chloro-5-(methylsulfonyl)pyridin-3-yl)acetamide

2-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine

Na2CO3

Toluene

→

N-(5-(4-acetylpiperazin-1-yl)pyridin-2-yl)-2-(2′-methyl-3-(methylsulfonyl)-2,4′-bipyridin-5-yl)acetamide

Disolventes

ethanol

H2O

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaAfter cooling to room temperature
2. 2
   Otrothe solvents were removed by rotary evaporation
3. 3
   OtroThe crude product was purified by reverse phase HPLC

Procedimiento

To a sealed tube were added N-(5-(4-acetylpiperazin-1-yl)pyridin-2-yl)-2-(6-chloro-5-(methylsulfonyl)pyridin-3-yl)acetamide 197-7 (30 mg, 0.07 mmol), 2-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 183-2 (22 mg, 0.10 mmol), Pd(PPh3)4 (4 mg, 0.003 mmol), Na2CO3 (22 mg, 0.20 mmol), Toluene (0.4 mL), H2O (0.4 mL) and ethanol (0.1 mL). The reaction mixture was stirred at 100° C. overnight. After cooling to room temperature, the solvents were removed by rotary evaporation. The crude product was purified by reverse phase HPLC to give N-(5-(4-acetylpiperazin-1-yl)pyridin-2-yl)-2-(2′-methyl-3-(methylsulfonyl)-2,4′-bipyridin-5-yl)acetamide 197. MS m/z 509.2 (M+1); 1H NMR 400 MHz (MeOD) δ 8.81(d, 1H), 8.52(d, 1H), 8.49(d, 1H), 7.97(s, 1H), 7.87(d, 1H), 7.47(s, 1H) 7.41(dd, 1H), 7.37(dd, 1H), 3.95(s, 2H), 3.68(t, 2H), 3.63(t, 2H), 3.15(t, 2H), 3.09(t, 2H), 2.92(s, 3H), 2.57(s, 3H), 2.09(s, 3H).

Fuente