Dimethylacetamide → 3-(5-Isopropyl-[1,2,4]triazol-1-yl)-5-(5-methyl-pyridin-2-yl)-benzoic acid methyl ester

Participants

Reaction Conditions

Reaction Steps

Isobutyramide (6.02 g, 69 mmol) and DMFDMA (9.22 mL) were added to 10 mL of DMA in a first flask, and the mixture was heated to 80° C. with stirring for one hour. In a second flask, a suspension of 3-hydrazino-5-(5-methyl-pyridin-2-yl)-benzoic acid methyl ester (6.42 g, 23 mmol) was suspended in acetic acid and heated t 80° C. The contents of the first flask were slowly added to the second flask, and the combined mixture was stirred at 80° C. for two hours. The reaction mixture was cooled and concentrated under reduced pressure. The residue was diluted with EtOAc, washed with saturated aqueous NaHCO3 and water, dried (MgSO4), filtered and concentrated under reduced pressure. The residue was purified via flash chromatography (hexanes/EtOAc 4:—2:1) to give 2.06 g of 3-(5-isopropyl-[1,2,4]triazol-1-yl)-5-(5-methyl-pyridin-2-yl)-benzoic acid methyl ester as a clear oil, MS (M+H)=337.

Provenance & Evidence