Reaktion #565

ord-7897aa67f78748769844b414acdceeae

Reaktionsgleichung

Cc1ccc(Oc2ccnc(Cl)c2)c(C)n1
Cc1ccc(Oc2ccnc(Cl)c2
Nc1ccc(S(=O)(=O)NCCN2CCOCC2)cc1
Nc1ccc(S(=O)(=O)NCCN
Cc1ccc(Oc2ccnc(Nc3ccc(S(=O)(=O)NCCN4CCOCC4)cc3)c2)c(C)n1
Cc1ccc(Oc2ccnc(Nc3cc
Ausbeute 60.7%

Lösungsmittel

Reaktionsbedingungen

Temperatur
150°CELSIUS

Vorschrift

In a 10 mL microwave reactor 3-(2-chloropyridin-4-yloxy)-2,6-dimethylpyridine (100 mg, 0.43 mmol) and 4-amino-N-(2-morpholinoethyl)benzenesulfonamide (122 mg, 0.43 mmol) were dissolved in DMA (5 mL) to give a tan solution.To the resultant solution Cesium carbonate (0.068 mL, 0.85 mmol) was added and sparged with nitrogen for 1 minute. Then Palladium(II) acetate (6.70 mg, 0.03 mmol) and 9,9-Dimethyl-4,5-bis(diphenylphosphino)xanthene (29.6 mg, 0.05 mmol) were added and the reaction mixture was sealed. The reaction was heated to150 °C for 25 minutes in the biotage microwave.The reaction was cooled to room temperature and LCMS shows reaction was completed. Reaction mixture was filtered through Celite Bed and washed with Dichloromethane. Filtrate was subjected to concentration to get DMA solution which was given to analytical department to purify using Mass based HPLC. After purification compound was isolated to get pale yellow solid of 4-(4-(2,6-dimethylpyridin-3-yloxy)pyridin-2-ylamino)-N-(2-morpholinoethyl)benzenesulfonamide (125 mg, 60.7 %)

Quelle

750 AstraZeneca ELN dataset