Sulfamic Acid → 2-(1-((1-(tert-Butoxycarbonyl)azetidin-3-yl)methyl)-6-fluoro-1H-indazol-3-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid

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Reaction Steps

To a stirred solution of tert-butyl 3-((6-fluoro-3-(7-formyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl)-1H-indazol-1-yl)methyl)azetidine-1-carboxylate (160 mg, 276 μmol) and sulfamic acid (161 mg, 1.65 mmol) in dioxane (5 mL) and water (2 mL), cooled to 0° C., was added a solution of sodium chlorite (32.4 mg, 358 μmol) and potassium dihydrogen phosphate (450 mg, 3.31 mmol) in water (3 mL) dropwise. The mixture was warmed to room temperature. After 2.5 h, the mixture was partitioned between ethyl acetate and water and the organic phase separated and washed with water then dried and concentrated in vacuo. A quantitative yield was assumed and the crude residue used directly in the next step without further purification.

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