Sodium Thiosulfate → propane-1-sulfonic acid [2-fluoro-3-(5H-pyrrolo[2,3-b]pyrazine-7-carbonyl)-phenyl]-amide

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Reaction Steps

To propane-1-sulfonic acid {2-fluoro-3-[hydroxy-(5H-pyrrolo[2,3-b]pyrazin-7-yl)-methyl]-phenyl}-amide (19, 74 mg, 0.20 mmol) in 1 mL of tetrahydrofuran, Dess-Martin periodane (95 mg, 0.22 mmol) and sodium bicarbonate (200 mg) were added. The reaction was stirred at room temperature for one hour, then poured into saturated aqueous sodium thiosulfate solution and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered and the filtrate concentrated under vacuum. The resulting material was purified by silica gel column chromatography eluting with 70% ethyl acetate in hexane. Appropriate fractions were combined and concentrated under vacuum to provide the desired compound (P-0008, 62 mg, 84%). MS (ESI) [M+H+]+=363.1.

Provenance & Evidence