Réaction #156352

Équation de réaction

Na2CO3

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

(6-Chloro-imidazo[1,2-b]pyridazin-3-yl)-quinoline

4-carbamoyl-3-chlorophenyboronic acid

DME

→

title compound

2-Chloro-4-(3-quinolin-6-ylmethyl-imidazo[1,2-b]pyridazin-6-yl)-benzamide

Solvants

DMF

DCM

Conditions de réaction

Traitement

1. 1
   AutreThe cool reaction mixture
2. 2
   Filtrationfiltered through a Celite pad
3. 3
   Lavagewashed with water
4. 4
   SéchageThe organic layer was dried over Na2SO4
5. 5
   Filtrationfiltered
6. 6
   Concentrationconcentrated in vacuo
7. 7
   ConcentrationWhile concentrating some crystals
8. 8
   FiltrationThe crystals were filtered off
9. 9
   Autredried

Mode opératoire

A microwave tube was charged with (6-chloro-imidazo[1,2-b]pyridazin-3-yl)-quinoline (Example 14, 150 mg, 0.509 mmol), 4-carbamoyl-3-chlorophenyboronic acid (304 mg, 1.527 mmol), DME (1.6 mL) and DMF (250 μL). 2 M Na2CO3 (763 μL, 1.527 mmol) was then added, followed by tetrakis-(triphenylphosphine)-palladium (21 mg, 0.025 mmol). The RM was heated at 90° C. for 24 h. The cool reaction mixture was poured in DCM, filtered through a Celite pad and washed with water. The organic layer was dried over Na2SO4, filtered and concentrated in vacuo. While concentrating some crystals appeared. The crystals were filtered off and dried to afford the title compound as a beige solid (tR 4.28 min (conditions 4), MH+=414.4, 1H-NMR in DMSO-d6: 8.85 (m, 1H); 8.32 (m, 1H); 8.24 (d, 1H); 8.11 (m, 1H); 8.07 (dd, 1H); 7.97 (m, 3H); 7.86 (d, 1H); 7.80 (s, 1H); 7.78 (dd, 1H); 7.70 (s, 1H); 7.61 (d, 1H); 7.51 (dd, 1H); 4.63 (s, 2H)).

Source