Sodium borohydride → HCID 9883654, compound

Participants

Reaction Steps

This Example was performed in a similar manner to Example 3. 3-(4-Chlorobenzo[b]thiophen-2-yl)-5,6-dihydroimidazo[2,1-b]-thiazole hydrobromide (1.5 g, see Example 1) was basified to give 3-(4-chlorobenzo[b]thiophen-2-yl)-5,6-dihydroimidazo[2,1-b]thiazole which was brominated to give 2-bromo-3-(4-chlorobenzo[b]thiophen-2-yl)-5,6-dihydroimidazo[2,1-b]thiazole hydrobromide (1.13 g) as a pale yellow solid, m.p. 227-229° C. This was reacted with ethylmagnesium chloride (2.0 M solution in ether; 3.75 ml) in tetrahydrofuran (20 ml) followed by dimethylformamide (0.83 ml) to give 3-(4-chlorobenzo[b]thiophen-2-yl)-5,6-dihydroimidazo[2,1-b]thiazole-2-carboxaldehyde. (0.65 g) as a red-brown solid after flash chromatography. This aldehyde was reduced with sodium borohydride (0.13 g) to give [3-(4-chlorobenzo[b]thiophen-2-yl)-5,6-dihydroimidazo[2,1-b]thiazol-2-yl]methanol (0.22 g) as a yellow solid, m.p. 170-172° C.

Provenance & Evidence