Sodium hydride → HCID 69059958, compound

Participants

Reaction Steps

(1H-Indazole-3-yl)-(3-methoxyphenyl) methanone (0.406 g, 1.6 mmol, example 14 step A) was dissolved in DMF (5 mL) at room temperature. Sodium hydride 95% (0.045 g, 1.9 mmol) was added. When the evolution of hydrogen had stopped, crotyl bromide (0.330 mL, 3.2 mmol) was added. After the reaction stirred for several minutes, lithium chloride (3.41 g, 80.4 mmol) was added directly to the reaction mixture. The temperature was elevated to 160° C., and stirred for several days. The reaction was monitored by thin layer chromatography. When most of the starting material was gone, the reaction was diluted with water and ethyl acetate. The organic layer was repeatedly extracted with brine to remove DMF. The organic layer was passed through a pad of silica gel, then purified by column chromatography, and crystallized with hexane to yield {1-[(2E)-but-2-enyl]-1H-indazol-3-yl}(3-hydroxyphenyl)methanone (0.163 g) as an off-white solid.

Provenance & Evidence