Réaction #68609

Équation de réaction

hydrazine hydrate

(6-phenylimidazo[1,2-b]pyridazin-3-yl)(quinolin-6-yl)methanone

KOH

diethylene glycol

→

6-((6-Phenylimidazo[1,2-b]pyridazin-3-yl)methyl)quinoline

Solvants

water

Conditions de réaction

Traitement

1. 1
   Autresealed
2. 2
   Extractionextracted with DCM (2×75 mL)
3. 3
   LavageThe combined organics were washed with brine (75 mL)
4. 4
   Séchagedried with MgSO4
5. 5
   Filtrationfiltered
6. 6
   Concentrationconcentrated
7. 7
   Autreto give a brown solid
8. 8
   Autrepurified by prep HPLC
9. 9
   Autreto give the product as the formic acid salt

Mode opératoire

A 10-20 mL microwave vial was charged with hydrazine hydrate (0.0312 ml, 0.642 mmol), (6-phenylimidazo[1,2-b]pyridazin-3-yl)(quinolin-6-yl)methanone (0.150 g, 0.428 mmol), KOH (0.0961 g, 1.71 mmol), and diethylene glycol (4.09 ml, 42.8 mmol), sealed, then placed in a Personal Chemistry microwave at 130° C. for 20 minutes after a 5 minute pre-stir. The mixture was diluted with water (75 mL), then extracted with DCM (2×75 mL). The combined organics were washed with brine (75 mL), then dried with MgSO4, filtered, and concentrated to give a brown solid, then purified by prep HPLC to give the product as the formic acid salt. MS (ESI pos. ion) m/z: 337 (MH+). Calc'd exact mass for C22H16N4: 336.

Source