2-Bromopyridine → HCID 178477852, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of trans-8-chloro-1-(4-phenyl-cyclohexyl)-5,6-dihydro-4H-2,3,5,10b-tetraaza-benzo[e]azulene hydrochloride (0.10 g, 0.24 mmol), 2-bromopyridine (0.057 g, 0.36 mmol) and cetyltrimethylammonium bromide (0.0040 g, 0.012 mmol) in toluene (2 ml) and 50% aqueous sodium hydroxide solution (0.04 ml) was degassed by freeze/thaw cycles. Addition of bis(tri-t-butylphosphine)palladium (0.012 g, 0.024 mmol) was followed by stirring at 90° C. for 18 h. The reaction mixture was partitioned between water (50 ml) and dichloromethane (50 ml). The layers were separated. The aqueous layer was extracted with one 50-ml portion of dichloromethane. The combined organic layers were dried over anhydrous sodium sulfate and concentrated in vacuo. Purification by flash-chromatography with n-heptane/ethyl acetate and ethyl acetate/2-propanol as eluent gave the title compound (0.004 g, 4%) as colorless oil.

Provenance & Evidence