Reacción #156479

Ecuación de reacción

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

water

NaBH4

→

{6-[6-(1-Methyl-1H-pyrazol-4-yl)-imidazo[1,2-b]pyridazin-3-ylmethyl]-imidazo[1,2-a]pyridin-3-yl}-methanol

Disolventes

MeOH

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroIt was quenched with water and EtOAc
2. 2
   OtroThe precipitate formed
3. 3
   Filtraciónwas filtered off
4. 4
   ConcentraciónThe filtrate was concentrated
5. 5
   Otrothen was triturated with MeOH
6. 6
   FiltraciónThe salt was filtered off
7. 7
   ConcentraciónThe filtrate was concentrated
8. 8
   Otrotriturated again with Et2O
9. 9
   FiltraciónThe precipitate was filtered off
10. 10
    Otroit was purified by flash chromatography (CombiFlash® Companion System®, with RediSep® silica gel column, 0 to 20% MeOH in DCM)
11. 11
    Otroto afford
12. 12
    Otroafter evaporation of the solvent the title compound as a yellow solid (tR 0.6 min (conditions 2), MH+=360)

Procedimiento

6-[6-(1-Methyl-1H-pyrazol-4-yl)-imidazo[1,2-b]pyridazin-3-ylmethyl]-imidazo[1,2-a]pyridine-3-carbaldehyde (Example 297, 50 mg, 0.140 mmol) was dissolved in MeOH (3 mL) and water (1 mL) then NaBH4 (2.6 mg, 0.070 mmol) was added. The RM was stirred at rt for 30 min. It was quenched with water and EtOAc. The precipitate formed was filtered off. The filtrate was concentrated then was triturated with MeOH. The salt was filtered off. The filtrate was concentrated and then triturated again with Et2O, The precipitate was filtered off and it 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 0.6 min (conditions 2), MH+=360).

Fuente