Reacción #44541

Ecuación de reacción

sodium tert-butoxide

2-(3-acetamidophenyl)-6-chloropyrazine

2,6-dichloropyridin-4-amine

BINAP

→

title compound

Rendimiento 7.8%

N-(3-(6-(2,6-dichloropyridin-4-ylamino)pyrazin-2-yl)phenyl)acetamide

Rendimiento 7.8%

Disolventes

toluene

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrowere reacted at 85° C. for 16 hours

Procedimiento

Using Method L, 2-(3-acetamidophenyl)-6-chloropyrazine (4a) (60 mg, 0.24 mmol), 2,6-dichloropyridin-4-amine (57.1 mg, 0.35 mmol), Pd(0)2 dba3 (9 mg, 0.01 mmol), BINAP (50 mg, 0.04 mmol), sodium tert-butoxide (33 mg, 0.34 mmol) and toluene (5 mL) were reacted at 85° C. for 16 hours. The same workup as for Method L followed by preparative TLC afforded 7 mg of title compound. Yield: 7.8%. 1H NMR (250 MHz, DMSO-d6) δ 2.08 (s, 3 H), 7.48 (t, 1 H, 7.9 Hz), 7.65 (d, 1 H, 8.0 Hz), 7.71 (d, 1 H, 7.6 Hz), 7.85 (s, 2 H), 8.30 (s, 1 H), 8.32 (bs, 1 H), 8.66 (s, 1 H), 10.10 (s, 1 H), 10.55 (s, 1 H); 13C NMR (62.9 MHZ, DMSO-d6) δ 23.9, 110.3, 117.47, 120.6, 121.2, 129.4, 133.4, 134.2, 136.3, 140.0, 148.3, 149.5, 149.7, 151.4, 168.3; m/z 374.1 [(M+H)+, calcd for C17H13Cl2N5O 373.0].

Fuente