Triethylamine → N-(3-ethyl-1-((1-ethyl-1H-pyrazol-3-yl)methyl)-1H-indazol-4-yl)-7-fluoroimidazo[1,2-a]pyridine-3-carboxamide

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Reaction Steps

7-Fluoroimidazo[1,2-a]pyridine-3-carboxylic acid (Preparation I; 224 mg, 1.25 mmol) was dissolved in anhydrous N-methylpyrrolidinone (0.2 M) and treated with triethylamine (0.35 mL, 2.5 mmol). When the mixture was homogeneous 2,4,6-trichlorobenzoyl chloride (0.20 mL, 1.31 mmol) was added dropwise. The mixture was stirred for 30 minutes at ambient temperature. 3-Ethyl-1-((1-ethyl-1H-pyrazol-3-yl)methyl)-1H-indazol-4-amine (0.30 mg, 1.11 mmol) was added in one portion and the sides of the flask were washed with anhydrous N-methylpyrrolidinone (2 mL). The mixture was heated to 90° C. and stirred for 16 hours. The mixture was allowed to cool and filtered through GF/F paper washing with ethyl acetate. The filtrate was concentration under reduced pressure and diluted with water to give a beige precipitate which was collected by filtration, washed with water and dried under high vacuum to give N-(3-ethyl-1-((1-ethyl-1H-pyrazol-3-yl)methyl)-1H-indazol-4-yl)-7-fluoroimidazo[1,2-a]pyridine-3-carboxamide (259 mg). MS m/z 432.1 (M+1, APCI+).

Provenance & Evidence