Potassium Phosphate, Tribasic → Pyridin-3-ylmethyl{4-[({3-[(tert-butoxycarbonyl)amino]-6-phenylpyridin-2-yl}amino)carbonyl]benzyl}carbamate

Participants

Reaction Conditions

Reaction Steps

Pyridin-3-ylmethyl [4-(aminocarbonyl)benzyl]carbamate (0.35 g, 1.24 mmol), di-tert-butyl(2-chloro-6-phenylpyridin-3-yl)imidodicarbonate (0.5 g, 1.24 mmol), Xanthphos (0.07 g, 0.12 mmol), potassium phosphate, tribasic (0.79 g, 3.70 mmol), and Pd2(dba)3 (0.57 g, 0.06 mmol) were combined in a 20 mL microwave vial and dioxane was added. The mixture was degassed for 20 mins, then sealed and heated to 100° C. overnight. Reaction was not complete and was continued another 24 h, for a total of 48 h at 100° C. The reaction was cooled to RT, diluted with saturated NaHCO3 solution and EtOAc, and the layers were separated. The water layer was extracted with EtOAc (2×100 mL). The combined organic fractions were washed with brine, dried over Na2SO4, filtered, and evaporated in vacuo. The residue was purified on a Biotage 65i column to yield pyridin-3-ylmethyl{4-[({3-[(tert-butoxycarbonyl)amino]-6-phenylpyridin-2-yl}amino)carbonyl]benzyl}carbamate. MS: cal'd 554 (MH+), exp 554 (MH+).

Provenance & Evidence