HCID 388066, compound → HCID 59326998, compound

Participants

Reaction Steps

A solution of 1-(tetrahydro-2H-pyran-2-yl)-1H-benzo[d]imidazole (39.5 g, 195 mmol) in anhydrous THF (300 ml) was cooled to 0° C. and treated with lithium bis(trimethylsilyl)amide (212 ml, 212 mmol) added dropwise over a 30 mins period. The reaction was allowed to stir for 1 hour and then methyl 4-(2-bromophenoxy)benzoate (50.00 g, 163 mmol), dissolved in 100 ml of anhydrous THF was added slowly to the reaction. The reaction was stirred for 1 hour at 0° C. and allowed to warm up to RT. After 1 hour, the reaction was cooled down to 0° C. and quenched with water (50 ml) dropwise. The reaction was diluted with 400 ml of Ethyl acetate and 400 ml of water. The layers were separated. The aqueous layer was extracted 2× (100 ml) with ethyl acetate. All the organic layers were combined, washed (2×) with an aqueous saturated solution of sodium bicarbonate, then with water and then brine. The organic layer was then dried with sodium sulfate and reduced to a smaller volume. The solid that precipitated out was filtered off, washed well with ether and dried to give product as solid. The mother liquor was concentrated and purified by column chromatography on silica gel using a gradient of 10 to 60% EtOAc in hexanes to give another batch of product.

Provenance & Evidence