4-Bromopyridine → HCID 86594094, compound

Participants

Reaction Conditions

Reaction Steps

The title compound, MS (ISP): m/e=440.4 (M+H+), was prepared as for example 209, steps (A) to (C). Step (B) was performed using 4-bromo-pyridine as follows: A suspension of (+/−)-[cis-1-(2-phenyl-cyclohexyl)-piperidin-4-yl]-amine (0.303 g, 1.17 mmol) in toluene (10 ml) was degassed with a flow of argon for 10 minutes. Palladium(II) acetate (8.0 mg, 0.036 mmol), rac-2,2′-bis(diphenylphosphino)-1,1′-binaphtyl (BINAP, 23.0 mg, 0.037 mmol), sodium tert-butoxide (0.280 g, 2.91 mmol) and 4-bromopyridine hydrochloride (0.194 g, 1.00 mmol) were added under argon. The flask was sealed and warmed to 70° C. for 3 hours. The mixture was diluted with ethyl acetate (10 ml) and diethyl ether (10 ml) and washed three times with saturated sodium chloride solution. The organic phase was dried with sodium sulphate and evaporated, yielding an orange oil. Purification was achieved by flash chromatography (dichloromethane/methanol/25% NH3 65:10:1). (+/−)-[cis-1-(2-Phenyl-cyclohexyl)-piperidin-4-yl]-pyridin-4-yl-amine (0.187 g, 47%) was obtained as a light yellow foam, MS (ISP): m/e=336.3 (M+H+). This was reacted with benzoyl chloride in step (C).

Provenance & Evidence