Water → HCID 58394277, compound

Participants

Reaction Conditions

Reaction Steps

Methyl 2-chloro-5-(1,3-thiazol-2-yl)isonicotinate (7-2, 6.5 g, 26 mmol, 1 equiv), (5-methylpyridin-3-yl)boronic acid (3.8 g, 28 mmol, 1.1 equiv), cesium carbonate (29 g, 89 mmol, 3.5 equiv) and PdCl2(dppf)-CH2Cl2 adduct (4.2 g 5.1 mmol, 0.2 equiv) were suspended in DMF (102 mL) and water (4.6 mL, 255 mmol, 10 equiv). The reaction mixture was heated for 45 minutes at 65° C., diluted with EtOAc (200 mL) and filtered through celite. The organic layer was washed with water (2×200 mL), dried over MgSO4 and concentrated. The residue was purified by normal phase column chromatography (40-80% EtOAc in hexanes) to afford the title compound (7-3) as a tan solid. ESI+MS[M+H]+C16H14N3O2S=312.1

Provenance & Evidence