Tetrahydrofuran → HCID 18187614, compound

Participants

Reaction Steps

A dry flask under nitrogen was charged with zinc chloride (16 mL, 0.5M in THF, 8 mmol), and a solution of phenylmagnesium chloride (4 mL, 2.0M in THF, 8 mmol). The mixture was heated to 50 C for 3 h then cooled to room temperature and transferred via cannula to a solution of 3,5-dibromopyridine (1.26 grams, 5.3 mmol), copper iodide (61 mg, 0.32 mmol), and bis(diphenylphosphino)ferrocene palladium dichloride (218 mg, 0.27 mmol) in 15 mL THF. The resulting mixture was heated to 50 C overnight. Sat'd ammonium chloride was added and the mixture was extracted with EtOAc. The organic portion was dried over sodium sulfate and concentrated. Flash chromatography (8/1 hexane/EtOAc) afforded 433 mg (33%) of the title compound. 1H NMR (400 MHz, CDCl3). δ4.02 (s, 2H), 7.18-7.4 (m, 8H), 7.65 (s, 1H).

Provenance & Evidence