Reaction #156479

Reaction equation

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

Solvents

MeOH

Conditions

Workup

1. 1
   OtherIt was quenched with water and EtOAc
2. 2
   OtherThe precipitate formed
3. 3
   Filtrationwas filtered off
4. 4
   ConcentrationThe filtrate was concentrated
5. 5
   Otherthen was triturated with MeOH
6. 6
   FiltrationThe salt was filtered off
7. 7
   ConcentrationThe filtrate was concentrated
8. 8
   Othertriturated again with Et2O
9. 9
   FiltrationThe precipitate was filtered off
10. 10
    Otherit was purified by flash chromatography (CombiFlash® Companion System®, with RediSep® silica gel column, 0 to 20% MeOH in DCM)
11. 11
    Otherto afford
12. 12
    Otherafter evaporation of the solvent the title compound as a yellow solid (tR 0.6 min (conditions 2), MH+=360)

Procedure

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).

Source