Tetrahydrofuran → 2,4-Dimethyl-6-phenyl-nicotinonitrile

Participants

Reaction Steps

Copper bromide (2.56 g, 17.49 mmol) was suspended in 20 mL of anhydrous THF, dropwisely added with magnesium bromide (3.0M ether, 11.66 mL, 34.99 mmol) at −78° C. and stirred for about 20 minutes. A 10 mL of anhydrous TNF was dropwisely added with a solution, wherein 2 chloro-6-phenyl-4-methyl-nicotinonitrile was dissolved, at the above temperature and then stirred for about 1 hour at room temperature. The mixture was added with a saturated solution of ammonium hydroxide and adjusted its pH to 10 with 1 N NaOH. Then, it was extracted with ethyl acetate, dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure. A silica gel column chromatography (5% EtOAc/Hexane) was performed on the resulting residue and 550 mg (55%) of 2,4-dimethyl-6-phenyl-nicotinonitrile was obtained in white solid.

Provenance & Evidence