Trifluoroacetic acid → [5-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)-6-fluoro-pyridin-2-yl]-(5-fluoro-pyridin-3-ylmethyl)-amine

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Reaction Steps

To 3-{6-[tert-butoxycarbonyl-(5-fluoro-pyridin-3-ylmethyl)-amino]-2-fluoro-pyridin-3-ylmethyl}-5-chloro-pyrrolo[2,3-b]pyridine-1-carboxylic acid tert-butyl ester (144, 0.280 g, 0.478 mmol) in 10.0 mL of dichloromethane, trifluoroacetic acid (1.00 mL, 13.0 mmol) was added and the reaction stirred at room temperature overnight. This was pooled with a separate reaction run similarly and concentrated under vacuum. The resulting material was combined with aqueous potassium carbonate and ethyl acetate and mixed. The aqueous layer was separated and the organic layer was dried over sodium sulfate, filtered and the filtrate concentrated under vacuum. The resulting material was purified by silica gel column chromatography eluting with 20% ethyl acetate in hexane. Appropriate fractions were combined and the solvent removed under vacuum to provide the desired compound (P-2001, 99 mg). MS (ESI) [M+H+]+=386.0.

Provenance & Evidence