Sulfamic Acid → 2-(6-chloro-4-fluoro-1H-indazol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid

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Reaction Steps

2-(6-Chloro-4-fluoro-1H-indazol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carbaldehyde (139 mg, 0.31 mmol) was dissolved in THF (4.7 ml) and water (1.6 ml) and sulfamic acid (291 mg, 3.0 mmol) was added. A solution of sodium chlorite (17 mg, 0.185 mmol) and potassium phosphate monobasic (232 mg, 1.7 mmol) in water (1.4 ml) was slowly added. After 1 h the reaction mixture was poured into ethyl acetate and water. The layers were separated and the aqueous layer was extracted once more with ethyl acetate. The combined organic layers were dried over sodium sulfate and concentrated to give 136 mg of 2-(6-chloro-4-fluoro-1H-indazol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid.

Provenance & Evidence