Cesium carbonate → Ethyl 5-(1-phenylvinyl)thiazolo[5,4-b]pyridine-2-carboxylate

Participants

Reaction Conditions

Reaction Steps

A mixture of ethyl 5-chlorothiazolo[5,4-b]pyridine-2-carboxylate (500 mg, 2.06 mmol), 1-phenylvinylboronic acid (366 mg, 2.47 mmol), Pd(Oac)2 (18.5 mg, 82.4 μmol), cesium carbonate (1.343 g, 4.12 mmol), and 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (S-Phos; 33.8 mg, 82.4 μmol) in toluene (10.0 mL) was sparged with argon, then heated at 90° C. for 21.5 h. The resulting brown solution was diluted with dichloromethane (30 mL) and filtered through a pad of silica gel (washing pad with ethyl acetate (3×30 mL)). The filtrate was concentrated in vacuo, and the residue was purified via column chromatography (silica gel, 0-70% EtOAc/hexanes) to afford ethyl 5-(1-phenylvinyl)thiazolo[5,4-b]pyridine-2-carboxylate as a light yellow solid. MS (ESI) m/z: Calculated: 310.1; Observed: 311.1 (M++1).

Provenance & Evidence