Boron tribromide → HCID 22729205, compound

Temperature

-8 °C

7-Methoxy-2-(5-methyl-1,3,4-oxadiazol-2-yl)benzo(b)furan (2 g) was dissolved in dichloromethane (50 ml) and boron tribromide (2 ml) was added dropwise with stirring at −8° C. The mixture was then stirred for 1 hr under ice-cooling and the reaction mixture was poured into ice water and extracted with chloroform. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to give red crystals (1.5 g) of 7-hydroxy-2-(5-methyl-1,3,4-oxadiazol-2-yl)benzo(b)furan. This compound and (S)-glycidyl nosylate (2 g) were dissolved in DMF (100 ml) and potassium carbonate (11 g) was added. The mixture was stirred at 50° C. for 2 hr. The reaction mixture was poured into ice water and extracted with ethyl acetate. The organic layer was washed with saturated aqueous ammonium chloride solution, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give an oily product (2 g). The oily product and 4-(naphthalen-1-yl)piperidine were dissolved in methanol (20 ml) and the mixture was refluxed under heating for 1 hr. After cooling, the solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (chloroform/methanol) to give the title compound (1.0 g) as a pale-yellow oil.

1. stirringThe mixture was then stirred for 1 hr under ice-
2. temperaturecooling
3. extractionextracted with chloroform
4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
5. concentrationconcentrated under reduced pressure

ORD record

ord-2ce318c84b874b328d35a28306fd1ade

Source dataset

uspto-grants-2004_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06720320B2