Toluene → HCID 21956528, compound

Participants

Reaction Steps

To toluene (1 mL) was added 3-methoxy-4-(pyridin-2-yl)-2′-nitrobenzanilide (97 mg, 0.28 mmol) and phosphorous pentachloride (56 mg, 0.27 mmol), and the mixture heated at reflux for 1 h. The resulting solution was cooled to rt and added to a solution of NaN3 (35 mg, 0.54 mmol) in DMF (2 mL). The mixture was heated at 90° C. for 1 h, cooled to rt, partitioned between EtOAc and water, and the organic layer concentrated. The crude product was purified by flash column chromatography on silica gel eluting with EtOAc:hexanes (0:1 to 1:1) to afford 2-{2-methoxy-4-[1-(2-nitrophenyl)-1H-tetraazol-5-yl]phenyl}pyridine as a yellow solid.

Provenance & Evidence