Tributylvinyltin → 5-(2,6-diethyl-phenyl)-1-(4-isopropyl-phenyl)-3-vinyl-1H-pyrrolo[2,3-c]pyridine

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-bromo-5-(2,6-diethyl-phenyl)-1-(4-isopropyl-phenyl)-1H-pyrrolo[2,3-c]pyridine (440 mg, 0.98 mmol), tributyl-vinyl-stannane (620 mg, 1.96 mmol), Pd(PPh3)4 (113 mg, 0.098 mmol), and DMF (5 mL) is heated to 100° C. for 3 h under nitrogen. The mixture is poured to a saturated aqueous KF solution (20 mL), and the resultant mixture is stirred for three hours at room temperature. The product is extracted with EtOAc (70 mL×3). The combined organic extracts are washed with water (100 mL×3) and brine (100 mL), dried (Na2SO4), and concentrated under reduced pressure. The residue is purified by chromatography on silica gel (Hexane/EtOAc, 10:1) to afford 5-(2,6-diethyl-phenyl)-1-(4-isopropyl-phenyl)-3-vinyl-1H-pyrrolo[2,3-c]pyridine as a colorless oil.

Provenance & Evidence