Cesium carbonate → Methyl 3-(1-methoxypropan-2-yloxy)-5-(4-(5-methyl-1,3,4-oxadiazol-2-yl)phenoxy)benzoate

Participants

Reaction Conditions

Reaction Steps

To a stirred suspension of Methyl 3-hydroxy-5-(1-methoxypropan-2-yloxy)benzoate (Intermediate 3) (7.88 g, 32.84 mmol, 1.3 equiv.), N,N-dimethylglycine hydrochloride (1 g, 7.69 mmol. 30 mole %), Cesium carbonate (16.5 g, 50.52 mmol, 2 equiv.), copper (II) iodide (0.488 g, 2.56 mmol, 0.1 mole %) in dry dioxane was added 2-(4-iodophenyl)-5-methyl-1,3,4-oxadiazole (7.2 g, 25.26 mmol, 1 equiv.) under nitrogen. The reaction mixture was heated up to reflux at 100° C. for 24 h. The reaction mixture was cooled, quenched with water and extracted with DCM. Combined organic washings were washed with water, brine, dried over Na2SO4, filtered and concentrated in vacuo to get the crude product. The crude product was purified by column chromatography using silica gel as stationary phase and EtOAc: petroleum ether as mobile phase to furnish the product (6.8 g) as thick liquid.

Provenance & Evidence