Butyl bromide → HCID 19014473, compound

Participants

Reaction Steps

6-Chloro-3-(4-pyridinylamino)benzo[b]thiophene (5 g, 19 mmol) was added portionwise as a powder to a suspension of sodium hydride (60% oil dispersion, 0.8 g, 20 mmol, washed with heptane) in 50 mL of dimethylformamide. After the anion formation was completed, 1-bromobutane (2.8 g, 20 mmol) was added. After stirring one hour, the reaction mixture was poured into ice-water and extracted with ethyl acetate. The organic extract was washed with water and saturated sodium chloride solution, and dried (anhydrous magnesium sulfate), filtered and concentrated. Elution of the residue through silica with 5% methanol in ethyl acetate via flash column chromatography afforded 3.7 g of an oil. Elution through alumina with ether via column chromatography afforded 3.3 g of an oil. Conversion to the hydrochloride salt in 10% methanol in ether afforded 3.2 g of white crystals, mp 259°-260° C.

Provenance & Evidence