Dichloromethane → HCID 57938632, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 1,1,1-trifluoromethanesulfonic acid 6-methoxy[1,5]naphthyridin-4-yl ester (1.0 g, 3.24 mmole) in dry dioxane (50 mL) at RT was added bis(pinacolato)diboron (1.07 g, 4.22 mmole), potassium acetate (0.95 g, 9.72 mmole), 1,1-bis(diphenylphosphino)ferrocene (0.09 g, 0.16 mmole) and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) complexed with dichloromethane (1:1) (0.13 g, 0.16 mmole). The reaction contents were heated to 80° C. for 24 h under nitrogen gas and then 1, 1-bis(diphenylphosphino)ferrocene (0.09 g, 0.16 mmole), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) complexed with dichloromethane (1:1) (0.13 g, 0.16 mmole), potassium carbonate (1.34 g, 9.72 mmole) and [2-(4-bromophenyl)ethyl]carbamic acid tert-butyl ester (0.97 g, 3.24 mmole) were added to the reaction pot. After 24 h of vigorous stirring at 80° C., the reaction contents were filtered through a scinter-glass funnel containing a bed of celite (EtOAc). The filtrate was concentrated under vacuum and purified on silica (EtOAc) to afford the title compound (0.76 g, 62%) as a tan solid: LC-MS (ES) m/e 380 (M+H)+.

Provenance & Evidence