Trifluoroacetic acid → 3-methoxy-5-(5-methyl-1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)-pyridin-2-ylamine

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Reaction Steps

In a round bottom flask, {5-[hydroxy-(5-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-methyl]-3-methoxy-pyridin-2-yl}-(4-methoxy-benzyl)-carbamic acid tert-butyl ester (127, 1 equivalent) is combined with 100 mL of acetonitrile, triethylsilane (18 equivalents), and trifluoroacetic acid (18 equivalents). The reaction is heated at reflux for 24 hours, then concentrated under vacuum. The resulting material is dissolved in 40 mL of trifluoroacetic acid and stirred at room temperature for 18 hours. This is concentrated under vacuum and combined with water and sodium bicarbonate, then extracted with ethyl acetate. The organic layer is washed with sodium bicarbonate, water, brine, then dried with magnesium sulfate, filtered and the filtrate is concentrated under vacuum. The resulting material is purified by silica gel column chromatography eluting with ethyl acetate and hexane. Appropriate fractions are combined and concentrated under vacuum to provide the desired compound.

Provenance & Evidence