Sodium Carbonate → 8-{3-[1-(4-Chloro-phenyl)-2-pyridin-4-yl-ethyl]-phenyl}-quinoline

Participants

Reaction Conditions

Reaction Steps

A solution of 4-[2-(3-bromo-phenyl)-2-(4-chloro-phenyl)-ethyl]-pyridine from Step 1 above (400 mg, 1.07 mmol), diboron pinacol ester (300 mg, 1.18 mmol), KOAc (315 mg, 3.2 mmol) and PdCl2(dppf) (26 mg, 0.032 mmol) in DMF (20 mL) was heated at 80° C. under N2 for 5 h. The resulting reaction mixture was cooled to 21° C., 8-bromoquinoline (290 mg, 1.4 mmol), Na2CO3 (2M, 1.61 mL, 3.2 mmol) and PdCl2(dppf) (26 mg, 0.032 mmol) was then added. The reaction mixture was stirred 18 h at 80° C., then diluted with a saturated ammonium chloride solution and ethyl acetate. The organic extracts were washed (H2O, brine), dried (MgSO4), filtered and concentrated. Purification by flash chromatography (eluting with hexane/ethyl acetate, 50:50 to 25:75) provided the 8-{3-[1-(4-chloro-phenyl)-2-pyridin-4-yl-ethyl]-phenyl}-quinoline compound (319 mg).

Provenance & Evidence