Potassium Hydroxide → propane-1-sulfonic acid 2,4-difluoro-3-[hydroxy-(5H-pyrrolo[2,3-b]pyrazin-7-yl)-methyl]-phenyl-amide

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Reaction Steps

To 5H-pyrrolo[2,3-b]pyrazine (3, 0.150 g, 1.26 mmol) and propane-1-sulfonic acid (2,4-difluoro-3-formyl-phenyl)-amide (8, 0.388 g, 1.47 mmol), 2.2 mL of methanol was added. This suspension was allowed to stir for 10 minutes, followed by the addition of potassium hydroxide (0.230 g, 4.10 mmol). The reaction was allowed to stir at room temperature for 7 hours, then poured into 5 mL of water and 5 mL of saturated ammonium chloride and extracted with 5 mL of ethyl acetate. The organic layer was separated and concentrated under vacuum, and the resulting residue was purified by silica gel column chromatography eluting with a gradient of 10 to 100% ethyl acetate in hexanes. Appropriate fractions were combined and concentrated under vacuum to give the desired compound (9, 243 mg). MS (ESI)[(M-18)+H+]+=365.1.

Provenance & Evidence