Hydrochloric Acid → HCID 69312695, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 2-(1H-pyrrol-3-yl)pyridine (0.072 g, 0.5 mmol), 1,3-dichloro-5-iodobenzene (0.163 g, 0.6 mmol), 1,10-phenanthroline (0.360 g, 2 mmol) and potassium phosphate (0.223 g, 1.05 mmol) in dioxane were degassed for 10 min, then copper (I) iodide (0.038 g, 0.2 mmol) was added and the mixture degassed a further 10 min. The mixture was heated to 110° C. for 4 h. The reaction mixture was quenched with brine, extracted with EtOAc (3×25 mL) and the combined organic extracts washed with brine. The organic phase was dried over Na2SO4, concentrated in vacuo and the residue was chromatographed on silica gel eluting with EtOAc:hexane (1:4) to afford a white solid. The crude material was dissolved in THF (5 mL), 1.2 eq. of 1M HCl in diethyl ether was added and the resulting precipitate was filtered to obtain 2-[1-(3,5-dichlorophenyl)-1H-pyrrol-3-yl]pyridine hydrochloride as a white solid. 1H-NMR (CD3OD, 300 MHz) δ 8.60 (d, 1H), 8.50 (dd, 1H), 8.41 (dd, 1H), 8.34 (d, 1H), 7.80-7.69 (m, 3H), 7.59 (dd, 1H), 7.50-7.49 (m, 1H), 7.11-7.09 (dd, 1H). MS (ESI) 289.0 (M++H).

Provenance & Evidence