Sodium Iodide → HCID 23081404, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-methyl-6-nitro-2,3-dihydro-imidazo[2,1-b]oxazol-2-ylmethyl methanesulfonate prepared in Example 41 (1.02 g, 3.67 mmol), 5-(4-bromophenyl)-3H-[1,3,4]oxadiazol-2-one (680 mg, 2.82 mmol), potassium carbonate (580 mg, 4.2 mmol), sodium iodide (890 mg, 5.94 mmol) and DMF (15 ml) was stirred at 100° C. for 3 hours. The reaction mixture was allowed to return to room temperature. To the solution, water was added, and the resulting solution was extracted with ethyl acetate twice. The organic phases were combined, washed with water three times, dried over magnesium sulfate and then filtered. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (methylene chloride/ethyl acetate=9/1) to afford 5-(4-bromophenyl)-3-(2-methyl-6-nitro-2,3-dihydro-imidazo[2,1-b]oxazol-2-ylmethyl)-3H-[1,3,4]oxadiazol-2-one (17.4 mg, yield 2%) as a light yellow powder.

Provenance & Evidence