Sodium Carbonate → HCID 68814364, compound

Participants

Reaction Steps

Add pyridine-4-boronic acid (2.361 g, 19.21 mmol) and 2 N sodium carbonate (19.21 mL, 38.42 mmol) to a solution of 5-iodo-N-methyl-N-propyl-isophthalamic acid benzyl ester (6.000 g, 13.72 mmol) in ethylene glycol dimethyl ether (206 mL) under nitrogen at room temperature. Add tetrakis(triphenylphosphine)palladium (0) (0.634 g, 0.549 mmol) and reflux for 20 h. Cool to room temperature and concentrate. Add ethyl acetate, separate the organic layer and extract the aqueous layer with ethyl acetate (4×). Wash the combined organic layers with H2O, saturated aqueous sodium chloride, dry (magnesium sulfate), concentrate and purify (silica gel chromatography, eluting with ethyl acetate) to give the title compound (56%).

Provenance & Evidence