Cesium carbonate → N-(3-(1H-tetrazol-1-yl)propyl)-2-fluoro-4-nitroaniline

Participants

Reaction Steps

To a mixture of 1-(3-chloropropyl)-1H-tetrazole (2.10 g, 14.33 mmol), cesium carbonate (4.66 g, 14.33 mmol) and a catalytic amount of KI in DMF (30 mL) in an ice bath was added 2-fluoro-4-nitroaniline (1.50 g, 9.61 mmol) in one portion. After the mixture was refluxed for 35 h, the mixture was cooled to rt and filtered. The filtrate was concentrated in vacuo. To the residue was added water (50 mL) and the resulting mixture was extracted with DCM (20 mL 2). The combined organic layers were washed with brine (20 mL×2) and concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=2:1) to give the title compound as oil (0.36 g, 10%).

Provenance & Evidence