Reacción #156367

Ecuación de reacción

6-(6-chloro-imidazo[1,2-b]pyridazin-3-ylmethyl)-7-fluoro-quinoline

3-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)pyrazol-1-yl]-azetidine-1-carboxylic acid tert-butyl ester

DME

K2CO3

→

title compound

3-{4-[3-(7-Fluoro-quinolin-6-ylmethyl)-imidazo[1,2-b]pyridazin-6-yl]-pyrazol-1-yl}-azetidine-1-carboxylic acid tert-butyl ester

Disolventes

EtOAc NaHCO3

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe organic phase was separated
2. 2
   Lavadowashed with brine (2×)
3. 3
   Secadothen dried over Na2SO4
4. 4
   Filtraciónfiltered
5. 5
   Concentraciónconcentrated in vacuo
6. 6
   OtroThe residue was purified by flash chromatography (CombiFlash® Companion System®

Procedimiento

A flask was charged with 6-(6-chloro-imidazo[1,2-b]pyridazin-3-ylmethyl)-7-fluoro-quinoline (Stage 173.1, 100 mg, 0.320 mmol), 3-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)pyrazol-1-yl]-azetidine-1-carboxylic acid tert-butyl ester (Stage 146.3), 168 mg, 0.480 mmol), DME (2 mL), Pd(PPh3)2Cl2 (11 mg, 0.05 mmol) and 2 M K2CO3 (432 μL, 0.863 mmol). The RM was heated at 95° C. for 2 h. The cool RM was diluted with EtOAc/NaHCO3. The organic phase was separated and washed with brine (2×) then dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by flash chromatography (CombiFlash® Companion System®, with a 4 g RediSep®: silica gel column, DCM/(DCM/MeOH 19:1)=100:0→0:100) to afford the title compound as a foam (tR 4.33 min (conditions 3), MH+=500.1).

Fuente