1,2-Dibromoethane → HCID 19886439, compound

Participants

Reaction Steps

A solution of 9.76 g (0.036 mol) of 4-(2-pyridinyl)-5-(4-fluorophenyl)-imidazole-2-thione, prepared as described in part d, in 250 ml of dry N,N-dimethylformamide was treated with 3.52 g (0.073 mol) of a 50% oil dispersion of sodium hydride. The solution was stirred for 30 minutes, followed by the addition of 13.95 g (0.074 mol) of 1,2-dibromoethane. The reaction mixture was stirred for 3 hours, and then poured into ice/water. The aqueous suspension was extracted several times with methylene chloride. The combined organic layers were washed with water, dried (MgSO4), and concentrated. The products were separated by chromatography on silica gel with 10% acetonitrile in methylene chloride and 25% acetonitrile in methylene chloride as eluants. Each product was recrystallized from acetonitrile-hexane to give the title Formula (I) compounds 5-(2-pyridinyl)-6-(4-fluoro-phenyl)-2,3-dihydroimidazo[2,1-b]thiazole, m.p. 152°-154° C., and 5-(4-fluorophenyl)-6-(2-pyridinyl)-2,3-dihydroimidazo[ 2,1-b]thiazole, m.p. 164°-166° C.

Provenance & Evidence