Water → ethyl 2-phenyl-5-(3-(tetrahydro-2H-pyran-2-yloxy)prop-1-ynyl)thiazole-4-carboxylate

Participants

Reaction Conditions

Reaction Steps

Nitrogen was bubbled through a solution of Ethyl 5-bromo-2-phenylthiazole-4-carboxylate (3.6 g, 11.5 mmol) and 2-(prop-2-ynyloxy)tetrahydro-2H-pyran (3.3 mL, 23.1 mmol) in THF (30 mL). Dichlorobis(triphenylphosphine)palladium (II) (405 mg, 0.6 mmol), copper (I) iodide (55 mg, 0.3 mmol), and triethylamine (TEA) (8 mL, 57.7 mmol) were added and the reaction mixture was heated at 100° C. for 30 min in a microwave reactor. The reaction mixture was poured into H2O and extracted with EtOAc. The combined organics were washed with brine, dried (MgSO4), and concentrated. The crude product was purified by MPLC eluting with pentane/EtOAc (0-50% gradient) to give ethyl 2-phenyl-5-(3-(tetrahydro-2H-pyran-2-yloxy)prop-1-ynyl)thiazole-4-carboxylate (3.8 g, 88% yield).

Provenance & Evidence