Sulfamic Acid → 2-(6-chloro-4-fluoro-1-methyl-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-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carbaldehyde (255 mg, 0.55 mmol) was dissolved in THF (8.3 ml) and water (2.8 ml). Sulfamic acid (517 mg, 5.3 mmol) was added. The reaction flask was cooled in an ice/water bath and a solution of sodium chlorite (104 mg, 1.15 mmol) and potassium phosphate monobasic (1.45 g, 10.6 mmol) in water (8 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 washed with water and sodium chloride solution, and dried over sodium sulfate. Evaporation of the solvent gave 270 mg of 2-(6-chloro-4-fluoro-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid as a light yellow solid. (M+H)+=476.

Provenance & Evidence