Triphenylphosphine → 7-[(2-Chloro-6-fluorobenzyl)oxy]-2,5-dimethylpyrazolo[1,5-a]pyridine-3-carboxylic Acid ethyl Ester

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Reaction Steps

A solution of 180 mg (0.76 mmol) of 7-hydroxy-2,5-dimethylpyrazolo[1,5-a]pyridine-3-carboxylic acid ethyl ester (Example 8A) in 7 ml of tetrahydrofuran was admixed with 247 mg (1.52 mmol) of 2-chloro-6-fluorobenzyl alcohol, 419 mg (1.60 mmol) of triphenylphosphine and 0.32 ml (1.60 mmol) of diisopropyl azodicarboxylate. The reaction mixture was stirred at room temperature for 1 h and concentrated under reduced pressure. The residue was purified by flash chromatography using a prepacked silica gel cartridge (mobile phase: cyclohexane-ethyl acetate, gradient 10% to 30%), which gave 280 mg (84% yield, 84% pure) of the target compound.

Provenance & Evidence