Reacción #156476

Ecuación de reacción

DMF

POCl3

3-(imidazo[1,2-a]pyridin-6-ylmethyl)-6-(1-methyl-1H-pyrazol-4-yl)imidazo[1,2-b]pyridazine

3-Imidazo[1,2-a]pyridin-6-ylmethyl-6-(1-methyl-1H-pyrazol-4-yl)-imidazo[1,2-b]pyridazine

→

6-[6-(1-Methyl-1H-pyrazol-4-yl)-imidazo[1,2-b]pyridazin-3-ylmethyl]-imidazo[1,2-a]pyridine-3-carbaldehyde

Disolventes

water

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe RM was warmed up to 120° C.
2. 2
   workup.STIRRINGstirred for 2 h
3. 3
   TemperaturaIt was cooled down to rt
4. 4
   ExtracciónIt was extracted twice with EtOAc
5. 5
   LavadoCombined organic layers was washed with brine
6. 6
   Secadodried over Na2SO4
7. 7
   Filtraciónfiltered
8. 8
   Concentraciónconcentrated
9. 9
   OtroThe residue was purified by flash chromatography (CombiFlash® Companion System®, with RediSep® silica gel column, 0 to 20% MeOH in DCM)
10. 10
    Otroto afford
11. 11
    Otroafter evaporation of the solvent the title compound as a yellow solid (tR 0.7 min (conditions 2), MH+=358)

Procedimiento

DMF (2 mL) was cooled down to 0° C. and then POCl3 (0.130 mL, 1.397 mmol) was added slowly. The solution was stirred for 10 min then it was warmed up to rt and the 3-(imidazo[1,2-a]pyridin-6-ylmethyl)-6-(1-methyl-1H-pyrazol-4-yl)imidazo[1,2-b]pyridazine (Example 10, 200 mg, 0.607 mmol) was introduced. The RM was warmed up to 120° C. and stirred for 2 h. It was cooled down to rt and water was added. It was extracted twice with EtOAc. Combined organic layers was washed with brine and dried over Na2SO4, filtered and concentrated. The residue was purified by flash chromatography (CombiFlash® Companion System®, with RediSep® silica gel column, 0 to 20% MeOH in DCM) to afford after evaporation of the solvent the title compound as a yellow solid (tR 0.7 min (conditions 2), MH+=358).

Fuente