Potassium Carbonate → Isopropyl 6-(2-hydroxypropan-2-yl)-3,4'-bipyridine-2'-carboxylate

Participants

Reaction Conditions

Reaction Steps

A mixture of crude 2-(isopropoxycarbonyl)pyridin-4-ylboronic acid (700 mg, ˜1.0 mmol), dppf(Pd)Cl2 (40 mg, 5 mol %), potassium carbonate (280 mg, 2.0 mmol) and 2-(5-bromopyridin-2-yl)propan-2-ol (216 mg, 1.0 mmol) in degassed toluene (3 mL), degassed water (1 mL) and degassed isopropanol (1 mL) was heated at 85° C. for 1 hour. The aqueous layer was discarded and the solvent removed under reduced pressure. The residue was purified by flash chromatography (rf: 0.53 in 20:1 ethyl acetate:methanol) to give isopropyl 6-(2-hydroxypropan-2-yl)-3,4′-bipyridine-2′-carboxylate (140 mg, 47% yield). 301.1 (M+1).

Provenance & Evidence