Sodium Carbonate → HCID 67496554, compound

Participants

Reaction Conditions

Reaction Steps

To a rt solution of 79.D (2.42 g, 7.4 mmol) and 2-methylpyridin-4-ylboronic acid (available from CombiPhos Catalysts, Inc.) (2.52 g, 18.4 mmol) in DMF (22 mL) was added saturated aqueous Na2CO3 (5 mL) followed by bis(triphenylphosphine)palladium(ii) chloride (265 mg, 0.37 mmol) After being purged with N2 for 15 mins, the mixture was stirred at 50° C. under N2 atmosphere for 3.5 hrs. The reaction solution was cooled, diluted with water (35 mL), treated with acetic acid to pH=7, and extracted with EtOAc (3×30 mL). The combined organic layers were washed with water, brine dried over MgSO4, and filtered. After removal of organic solvent under reduced pressure, purification of the residue by flash chromatography on silica gel using 0-6% MeOH/CH2Cl2 for elution gave the title product 79.E as pale yellow solid (1.51 g, 60%).

Provenance & Evidence