Toluene → 2-Bromo-6-(2,5-dimethyl-1H-pyrrol-1-yl)pyridine

Participants

Reaction Steps

To a 1 L round-bottomed flask equipped with Dean-Stark trap, condenser, and nitrogen inlet were added 21.3 g (123 mmol) 2-amino-6-bromopyridine, 400 mL toluene, 14.1 g (123 mmol) acetonylacetone, and 20 drops acetic acid. The reaction was refluxed 5 days (tlc in 1/1:ethyl acetate/hexane, Rf=0.8(product), 0.5 (starting material)), cooled, poured into ethyl acetate, washed with saturated aqueous sodium bicarbonate solution and brine, dried over sodium sulfate, and evaporated. The residue was chromatographed on silica gel using 5% methanol in methylene chloride to afford 14.4 g(47%) of the product as a low-melting yellow solid.

Provenance & Evidence