1,2-Dimethoxyethane → 6-(6-{1-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-1H-pyrazol-4-yl}-imidazo[1,2-b]pyridazin-3-ylmethyl)-quinoline

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

6-(6-Chloro-imidazo[1,2-b]pyridazin-3-ylmethyl)-quinoline (Example 14, 500 mg, 1.679 mmol) was introduced in a microwave reactor together with 1-[2-(tetrahydro-pyran-2-yloxy)ethyl]-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole (Stage 171.4, 812 mg, 2.52 mmol) and DME (10 mL). The solution was degassed with argon before adding Pd(PPh3)2Cl2 (36 mg, 0.051 mmol) and 2 M K2CO3 (2.267 mL, 4.53 mmol). The mixture was stirred at 90° C. for 5.5 h. The RM was taken up with EtOAc and washed with NaHCO3 and brine. The organic layer was dried over Na2SO4, filtered and concentrated in vacuo to afford a first batch of the desired product as a brownish oil (80% pure). 10% of the residue was dissolved in DCM and purified by flash chromatography (DCM/MeOH=100:0→93.5:6.5) to afford the title compound as a brownish oil (tR 2.30 min (8), MH+=455.1).

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