Dichloromethane → 1,1-Dimethylethyl (2-(5-[6-(methyloxy)-1,5-naphthyridin-4-yl]-2-pyridinyl}ethyl)carbamate

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 1,1,1-trifluoromethanesulfonic acid 6-methoxy[1,5]naphthyridin-4-yl ester (2.0 g, 8.42 mmole) in dry dioxane,(75 mL) at RT was added bis(pinacolato)diboron (2.14 g, 8.43 mmole), potassium acetate (1.91 g, 19.4 mmole), 1,1-bis(diphenylphosphino)ferrocene (0.18 g, 0.32 mmole) and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) complexed with dichloromethane (1:1) (0.26 g, 0.32 mmole). The reaction contents were heated to 80° C. for 24 h under nitrogen gas and then 1,1-bis(diphenylphosphino)ferrocene (0.18 g, 0.32 mmole), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) complexed with dichloromethane (1:1) (0.26 g, 0.32 mmole), potassium carbonate (2.68 g, 19.44 mmole) and 1,1-dimethylethyl [2-(5-bromo-2-pyridinyl)ethyl]carbamate (1.94 g, 6.48 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 (1.52 g, 62%) as a tan solid: LC-MS (ES) m/e 381 (M+H)+.

Provenance & Evidence