Boron tribromide → N-(5-bicyclo[2.2.1]heptanyl-methyl)-2-[3-(4-hydroxy-phenyl)-propylsulfanyl]-pyridine-3-carboxylic acid amide

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Reaction Steps

A solution of 483 mg (1.18 mmol) of N-(5-bicyclo[2.2.1]heptanyl-methyl)-2-[3-(4-methoxyphenyl)-propylsulfanyl]-pyridine-3-carboxylic acid amide (exemplary compound 56) in DCM (50 ml) was cooled to −60° C.; 11.8 ml (11.8 mmol, 1M in DCM) of boron tribromide were added at that temperature and stirring was carried out for 90 min at −60° C. After warming to RT, the mixture was quenched with a 1M aq. NaHCO3 sol. and the phases were separated. The aqueous phase was extracted with EA and the organic phases were combined, washed with water, dried over MgSO4, filtered and concentrated in vacuo. Crystallization (hexane/EA 2:1) of the residue yielded 393 mg (0.99 mmol, 84%) of N-(5-bicyclo[2.2.1]heptanyl-methyl)-2-[3-(4-hydroxy-phenyl)-propylsulfanyl]-pyridine-3-carboxylic acid amide. MS: m/z 397.2 [M+H]+.

Provenance & Evidence