Pyrrole → 1-(1H-inden-2-yl)-1H-pyrrole

Participants

Reaction Steps

In three-necked round-bottom flask (1 L), equipped with an Allihn condenser and magnetic stirrer bar and under an argon atmosphere, to a mixture of 49.0 g (231 mmol) of anhydrous K3PO4, 30.0 g (154 mmol) of 2-bromo-1H-indene, and 11.5 ml (11.1 g, 165 mmol) of pyrrole in 500 ml of toluene and 50 ml of DME, 4.59 g (15.4 mmol) of 2-[di(tert-butyl)-phosphino]biphenyl and 1.73 g (7.70 mmol) of Pd(OAc)2 were added at ambient temperature. This mixture was stirred at room temperature for 72 hours. The reaction mixture was filtered through the layer (d 100 mm, l 40 mm) of SilicaGel 60 (40-63 um) on a glass frit funnel. The SilicaGel layer was additionally washed by 200 ml of methyl-tert-butyl ether (MTBE). The combined extract was evaporated to dryness. The crude product was purified using flash chromatography (SilicaGel 60, 40-63 um, d 40 mm, l 500 mm; eluent hexanes/MTBE=10/1). This procedure gave 5.62 g (20%) of white crystalline product.

Provenance & Evidence