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

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Reaction Steps

In a round bottom flask, 5-fluoro-1H-pyrrolo[2,3-b]pyridine (155, 0.115 g, 0.845 mmol) was combined with (6-fluoro-5-formyl-pyridin-2-yl)-(6-methoxy-pyridin-3-ylmethyl)-carbamic acid tert-butyl ester (156, 0.397 g, 1.10 mmol), 2.60 mL of acetonitrile, trifluoroacetic acid (0.325 mL, 4.22 mmol) and triethylsilane (0.810 mL, 5.07 mmol) and the reaction was heated to reflux for 3 hours. The reaction was poured into water and extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, filtered and the filtrate concentrated under vacuum. The resulting material was purified by silica gel column chromatography eluting with ethyl acetate in hexane. Appropriate fractions were combined and concentrated under vacuum to provide the desired compound (P-1622, 28 mg). MS (ESI) [M+H+]+=382.1.

Provenance & Evidence