3-Pyridinylboronic acid → 2-(3-Ethyl-ureido)-7-pyridin-3-yl-[1,2,4]triazolo[1,5-a]pyridine-5-carboxylic acid ethyl ester

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Reaction Conditions

Reaction Steps

A suspension of the product of Step 1 (0.145 g, 0.407 mmol), 3-pyridylboronic acid (0.092 g, 0.750 mmol), sodium acetate trihydrate (0.308 g, 2.08 mmol), and 0.013 g Pd(dppf)Cl2-DCM in a mixture of 7:3:2 DME/water/EtOH (6 mL) was heated to 80° C. for 30 min in a closed vial in a CEM microwave reactor. The reaction was then partitioned between saturated sodium bicarbonate and DCM and the organic layer was collected. The aqueous layer was extracted with DCM (2×25 mL) and the combined organic layers were then extracted with 1N HCl (3×10 mL). The combined aqueous extracts were then neutralized with solid sodium bicarbonate and extracted with DCM (3×20 mL). The combined organic layers were then dried over sodium sulfate and evaporated in vacuo to give 2-(3-ethyl-ureido)-7-pyridin-3-yl-[1,2,4]triazolo[1,5-a]pyridine-5-carboxylic acid ethyl ester as a powder. MS (APCI+)=355.2

Provenance & Evidence