1,4-Dioxane → HCID 86709321, compound

Participants

Reaction Conditions

Reaction Steps

To a vial was added (E)-7-bromo-3-chloro-6′,7′-dihydro-2′H-spiro[chromeno[2,3-c]pyridine-5,5′-[1,4]oxazepin]-3′-amine (80 mg, 0.203 mmol), potassium phosphate (129 mg, 0.608 mmol), 2-fluoropyridin-3-ylboronic acid (30.0 mg, 0.213 mmol), 1,1-bis[(di-t-butyl-p-dimethylaminophenyl]palladium(ii) chloride (7.18 mg, 10.14 μmol), dioxane (1014 μL), water (338 μL). The resulting mixture was purged with N2 gas and heated at 90° C. in microwave reactor for 25 mins. It was diluted with water and extracted into EtOAc. The organic extract was washed with saturated NaCl aqueous solution, dried over MgSO4, filtered and concentrated to give the crude material as a orange solid. The crude material was absorbed onto a plug of silica gel and purified by chromatography through a gold Redi-Sep pre-packed silica gel column (12 g), eluting with a gradient of 50% to 80% DCM/MeOH/NH4OH (90/10/1) in 40% EtOAc in Heptane, to provide (E)-3-chloro-7-(2-fluoropyridin-3-yl)-6′,7′-dihydro-2′H-spiro[chromeno[2,3-c]pyridine-5,5′-[1,4]oxazepin]-3′-amine as off-white solid.

Provenance & Evidence