Hydrochloric Acid → 5-Bromo-2-chloro-4-methyl-3-(3-trifluoromethyl-phenyl)-pyridine

Participants

Reaction Conditions

Reaction Steps

To a suspension of copper (II) chloride (421 mg, 3.92 mmol) and t-butyl nitrite (466 μL, 3.92 mmol) in dry MeCN (12 mL) at 70° C. was added 5-bromo-4-methyl-3-(3-trifluoromethyl-phenyl)-pyridin-2-ylamine (Int. 1, 864 mg, 2.61 mmol) dropwise as a solution in MeCN (3 mL) over 5 mins. The reaction mixture was stirred at 70° C. for 3.5 hrs then poured onto 5 N aqueous HCl (20 mL). The reaction mixture was extracted with EtOAc (4×20 mL) then the combined organic extracts were dried (Na2SO4), filtered and evaporated in vacuo. The resultant residue was purified by flash chromatography, eluting with a gradient of 0-100% EtOAc in cyclohexane to give the title compound as an orange solid (184 mg).

Provenance & Evidence