Reaktion #156360

Reaktionsgleichung

NaH

3-Chloroaniline

6-(6-chloro-imidazo[1,2-b]pyridazin-3-ylmethyl)-quinoline

→

title compound

(3-Chloro-phenyl)-(3-quinolin-6-ylmethyl-imidazo[1,2-b]pyridazin-6-yl)-amine

Lösungsmittel

NMP

EtOAc

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe mixture was then heated to 160° C. for 10 min
2. 2
   Waschenwashed with water (3×)
3. 3
   ExtraktionThe aqueous layer was extracted with EtOAc (3×)
4. 4
   TrocknenThe combined organic layers were dried over Na2SO4
5. 5
   Filtrationfiltered
6. 6
   Einengenconcentrated
7. 7
   SonstigeThe residue was purified by flash chromatography (Flashmaster)
8. 8
   Sonstigecrystallized in Et2O

Vorschrift

NaH (34 mg, 0.85 mmol) was suspended in NMP (1.5 mL) under argon. 3-Chloroaniline (108 μL, 1.017 mmol) was added and the RM was heated to 85° C. After 10 min, 6-(6-chloro-imidazo[1,2-b]pyridazin-3-ylmethyl)-quinoline (Example 14, 100 mg, 0.339 mmol) was added and the RM was stirred at 85° C. for 1 h. The mixture was then heated to 160° C. for 10 min. The mixture was diluted with EtOAc and washed with water (3×). The aqueous layer was extracted with EtOAc (3×). The combined organic layers were dried over Na2SO4, filtered and concentrated. The residue was purified by flash chromatography (Flashmaster) and crystallized in Et2O to afford the title compound as a yellow solid (tR 4.99 min (conditions 4), MH+=386.1, 1H-NMR in DMSO-d6: 9.57 (s, 1H); 8.82 (m, 1H); 7.93 (m, 3H); 7.86 (m, 1H); 7.71 (m, 1H); 7.56 (s, 1H); 7.47 (dd, 1H); 7.43 (m, 1H); 7.25 (t, 1H); 6.99 (m, 1H); 6.85 (d, 1H); 4.50 (s, 2H)).

Quelle