Sodium Carbonate → 3-Amino-6-(4-(3-(tert-butyldimethylsilyloxy)propyl)phenyl)-N-(pyridin-3-yl)-pyrazine-2-carboxamide

Participants

Reaction Steps

A mixture of the product of step (ii) (9.84 g, 30 mmol), bis(pinacolato)diboron (11.4 g, 45 mmol), KOAc (9 g, 90 mmol) and Pd(dppf)Cl2 (1 g, 1.5 mmol) in dioxane (200 mL) was stirred and degassed with N2 (×3). The mixture was stirred at 80° C. under a N2 atmosphere for 3 hours. The reaction mixture was cooled to room temperature. Water (25 mL) and Na2CO3 (10 g, 90 mmol) were added to the mixture. The mixture was stirred for 10 minutes before the product of step (v) (7.9 g, 27 mmol) and Pd(dppf)Cl2 (0.5 g, 0.7 mmol) were added. The resulting solution was degassed again with N2 (×3). The reaction mixture was stirred at 90° C. under a N2 atmosphere for additional 10 hours. Na2SO4 was added, filtered and the filtrate concentrated in vacuo. The crude product was purified by column chromatography with PE:EtOAc=5:1 to 3:1 as eluent to afford the subtitle compound (vi) as a yellow solid (7.8 g).

Provenance & Evidence