1,4-Dioxane → HCID 67383456, compound

Participants

Reaction Conditions

Reaction Steps

To a vial was added 3-chloro-7-(2-fluoropyridin-3-yl)-5′-(methoxymethyl)-5′H-spiro[chromeno[2,3-c]pyridine-5,4′-thiazol]-2′-amine (715 mg, 1.61 mmol), potassium phosphate (1.20 g, 5.65 mmol), (2-fluoropyridin-4-yl)boronic acid (910 mg, 6.46 mmol), and then dioxane (8.1 mL) and water (2.7 mL) were added. The mixture was purged with N2 and finally 1,1-bis[(di-t-butyl-p-dimethylaminophenyl]palladium(II) chloride (114 mg, 0.16 mmol) was added. The resulting mixture was then heated 135° C. in a microwave for 15 min. The reaction mixture were diluted with EtOAc and water. The organic extract was washed with brine, dried over MgSO4, filtered and concentrated in vacuo to give the crude material as a orange solid. Small amount of DCM was added and light brown precipitate formed. After filtration through Buchner funnel gave (4′S,5′S)-7-(2-fluoropyridin-3-yl)-3-(2-fluoropyridin-4-yl)-5′-(methoxymethyl)-5′H-spiro[chromeno[2,3-c]pyridine-5,4′-thiazol]-2′-amine (523 mg, 1.04 mmol, 64% yield) as light brown solid.

Provenance & Evidence