Water → 2-(3-chloro-6-fluoro-imidazo[1,5-a]pyridin-1-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid

関与物質

反応条件

反応手順

In a round-bottomed flask, 2-(6-fluoro-imidazo[1,5-a]pyridin-1-yl)-5-(2-trimethylsilanylethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carbaldehyde (254 mg, 0.55 mmol) was suspended in THF (10 ml) and water (2 ml). The suspension was cooled to 0° C. and sulfamic acid (324 mg, 3.33 mmol) was added. Then, a solution of sodium chlorite (80%, 88 mg, 0.78 mmol) and potassium dihydrogen phosphate (907 mg, 6.67 mmol) in water (6 ml) was added dropwise over 10 min. After the addition was complete, the ice bath was removed and the reaction mixture was stirred at room temperature for 4 h. The reaction mixture was diluted with water and extracted with EtOAc (2×). The combined organic layers were washed with water and brine then dried over sodium sulfate, filtered and concentrated. The residue was triturated with hexanes to afford 184 mg of 2-(3-chloro-6-fluoro-imidazo[1,5-a]pyridin-1-yl)-5-(2-trimethylsilanylethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid as a light green powder which was used without further purification.

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