4-(Methylsulfonyl)aniline → 4-(2,6-Dimethylpyridin-3-yloxy)-N-(4-(methylsulfonyl)phenyl)pyridin-2-amine

Participants

Reaction Conditions

Reaction Steps

In a 10 mL microwave reactor 3-(2-chloropyridin-4-yloxy)-2,6-dimethylpyridine (100 mg, 0.43 mmol) and 4-(methylsulfonyl)aniline (73.0 mg, 0.43 mmol) were dissolved in DMA (3 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-(2,6-dimethylpyridin-3-yloxy)-N-(4-(methylsulfonyl)phenyl)pyridin-2-amine (80 mg, 50.8 %)

Provenance & Evidence