Sodium Iodide → Methyl 4-{[(4'-chloro-4-methylbiphenyl-3-yl)acetyl](prop-2-yn-1-yl)amino}-1,3-thiazole-5-carboxylate

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Reaction Steps

600 mg (1.5 mmol) of methyl 4-{[(4′-chloro-4-methylbiphenyl-3-yl)acetyl]amino}-1,3-thiazole-5-carboxylate were dissolved in 20 ml of acetonitrile, and 1.2 g (3.7 mmol) of cesium carbonate, 449 mg (3 mmol) of sodium iodide and 0.33 ml (3 mmol, 80% pure) of propargyl bromide were added. The mixture was then stirred at RT for 12. The resulting suspension was filtered. The mother liquor was concentrated by evaporation. The residue was taken up in water and the solution was extracted with dichloromethane. The organic phase was dried and concentrated by evaporation. The residue was taken up in acetonitrile and chromatographed (acetonitrile/water (0.05% trifluoroacetic acid 20/80 to 100/0)). This gave 415 mg of methyl 4-{[(4′-chloro-4-methylbiphenyl-3-yl)acetyl](prop-2-yn-1-yl)amino}-1,3-thiazole-5-carboxylate.

Provenance & Evidence