5-Methylpyridine-3-boronic acid → 4-(azetidine-1-carbonyl)-2-methyl-2H-pyrazole-3-carboxylic acid [2-(5-methyl-pyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridin-7-yl]-amide

Participants

Reaction Steps

The product was prepared in the same manner as described in example 66 using 4-(azetidine-1-carbonyl)-N-(2-bromo-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-1-methyl-1H-pyrazole-5-carboxamide (150 mg, 371 μmol) and 5-methylpyridin-3-ylboronic acid (76.2 mg, 557 μmol) as starting materials. The crude material was applied on silicagel and purified by flash chromatography over a 50 g NH2-silicagel column using heptane/ethyl acetate 20-100% as eluent affording 4-(azetidine-1-carbonyl)-2-methyl-2H-pyrazole-3-carboxylic acid [2-(5-methyl-pyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridin-7-yl]-amide (90 mg, 19.4%) as a light brown solid. mp: 262-264° C., MS: m/z=417.3 (M+H+)

Provenance & Evidence