5-Bromo-[1,2,4]triazolo[1,5-a]pyridin-2-amine → HCID 178517536, compound

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Reaction Steps

(2-Amino-[1,2,4]triazolo[1,5-a]pyridin-5-yl)(2-methoxypyridin-4-yl)methanone. 5-Bromo-[1,2,4]triazolo[1,5-a]pyridin-2-amine (10 g, 46.9 mmol) was suspended in anhydrous tetrahydrofuran (300 mL) and cooled to −78° C. n-Butyl lithium (64.5 mL, 103 mmol) was added over 30 minutes and the solution was allowed to stir for 1 h (brown suspension). N,2-dimethoxy-N-methylisonicotinamide (9.21 g, 46.9 mmol) dissolved in tetrahydrofuran (50 mL, dried over molecular sieves) was added dropwise via syringe (brown suspension). The reaction was stirred for 1 h and allowed to slowly warm to room temperature for 3 h (reaction became a clear solution as it warmed up to room temperature). LCMS analysis showed the desired product. The reaction was quenched by dropwise addition of water (20 mL) and then neutralized with aqueous hydrochloric acid to pH=7. Flash chromatography (30-100% ethyl acetate in hexane) gave the desired product as a light yellow solid (6.5 g, 24.14 mmol, 51.4% yield). MS (ESI) m/z 270.2 [M+1]+.

Provenance & Evidence