1-Bromopropane → HCID 19360190, compound

Participants

Reaction Steps

6-Chloro-3-(4-pyridinylamino)benzo[b]thiophene (4.2 g, 16.1 mmol) was added portionwise as a powder to an ice-cooled suspension of sodium hydride (60% oil dispersion, 0.8 g, 20 mmol, washed with heptane) in 25 mL of dimethylformamide. After the anion formation was completed, 1-bromopropane (2 g, 16.3 mmol) was added. After one hour the reaction mixture was poured into ice-water and extracted with ether. The organic extract was washed with water and saturated sodium chloride solution, and dried (anhydrous magnesium sulfate), filtered and concentrated to a brown oil. Elution through silica with 10% methanol in ethyl acetate via flash column chromatography yielded 3.5 g of an amber oil. Conversion to the hydrochloride salt in 10% methanol in ether afforded 3.7 g of a pale yellow powder, mp 276°-277° C.

Provenance & Evidence