Citric Acid → (4-aminopyridin-2-yl)[1-(2-{[tert-butyl(dimethyl)silyl]oxy}-1,1-dimethylethyl)-1H-pyrrolo[3,2-c]pyridin-3-yl]methanone

Participants

Reaction Steps

To a solution of [1-(2-{[tert-butyl(dimethyl)silyl]oxy}-1,1-dimethylethyl)-1H-pyrrolo[3,2-c]pyridin-3-yl]{4-[(diphenylmethylene)amino]pyridin-2-yl}methanone (Preparation 35, 1.4 g, 2.38 mmol) in THF (3 mL) was added a 1M solution of citric acid (2.5 g, 11.9 mmol) and the reaction was stirred at room temperature for 4 hours. A 10% aqueous solution of potassium carbonate was added carefully, and the mixture extracted into EtOAc (3×50 mL). The organic layers were combined, dried over MgSO4 and concentrated in vacuo. To the residue was added DCM and a solid precipitated that was filtered and dried. The mother liquors were purified using silica gel column chromatography eluting with 100% heptanes to 100% EtOAc to 5% MeOH in EtOAc to afford further material. The solids were combined to afford the title compound (70%, 710 mg).

Provenance & Evidence