2-(Dicyclohexylphosphino)biphenyl → HCID 58397894, compound

Participants

Reaction Conditions

Reaction Steps

A degassed solution of 2-(dicyclohexylphosphino)biphenyl (12.7 mg, 36.3 μmol) and palladium(II) acetate (4.08 mg, 18.2 μmol) in dioxane (2 mL) was stirred for 10 minutes at room temperature, then a solution of N-(3,3-difluoropiperidin-4-yl)-8-(2,3,4-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine (87 mg, 227 μmol), 5-chloro-3-methyl-1,2,4-thiadiazole (30.5 mg, 227 μmol) and sodium tert-butoxide (32.7 mg, 340 μmol) in dioxane (2 mL) was added. Through the solution was bubbled argon for 5 minutes, then heated to 150° C. in the microwave for 60 minutes. Again a degassed solution of 2-(dicyclohexylphosphino)biphenyl (12.7 mg, 36.3 μmol) and palladium(II) acetate (4.08 mg, 18.2 μmol) in dioxane (2 mL) was added, followed by 5-chloro-3-methyl-1,2,4-thiadiazole (30.5 mg, 227 μmol) and heated to 150° C. in the microwave for further 60 minutes. Again a degassed solution of 2-(dicyclohexylphosphino)biphenyl (12.7 mg, 36.3 μmol) and palladium(II) acetate (4.08 mg, 18.2 mmol) in dioxane (2 mL) was added, followed by 5-chloro-3-methyl-1,2,4-thiadiazole (30.5 mg, 227 μmol) and heated to 150° C. in the microwave for further 60 minutes. The crude material was purified by flash chromatography (silica gel, 70 g, 0% to 15% MeOH/NH4OH (9:1) in dichloromethane) and then by preparative HPLC. The title compound was obtained as white foam (42 mg, 38%).

Provenance & Evidence