Potassium Phosphate, Tribasic → tert-butyl 3-(4-(2-(3-ethylureido)-6-fluorobenzo[d]thiazol-5-yl)-2-oxopyridin-1(2H)-yl)pyrrolidine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

A solution of 1-(5-bromo-6-fluoro-benzothiazol-2-yl)-3-ethyl-urea (0.07 g, 0.31 mmol), tert-butyl 3-(2-oxo-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-1(2H)-yl)pyrrolidine-1-carboxylate (0.24 g, 0.62 mmol) and K3PO4 (0.13 g, 0.62 mmol) in DMF-H2O (5.0 mL, 3:2) was degassed by flushing with nitrogen for 15 min. Dichlorobis(triphenylphosphine)-palladium(II) (0.022 g, 0.03 mmol) was then added to the reaction mixture followed by degassing with nitrogen for another 15 min. The resulting reaction mixture was then heated to 80° C. for 2 h. After the completion of the reaction (TLC monitoring), the reaction mixture was cooled to room temperature and poured onto ice-cold water followed by extraction with EtOAc (3×50 mL). The combined organics was washed with brine, dried (Na2SO4), filtered and concentrated under reduced pressure. The crude was then purified over silica gel (100-200 M, 1.50% MeOH-DCM) to obtain the desired product (0.056 g, 36%). MS: 502.20 (M+H)+.

Provenance & Evidence