Acetonitrile → 2-[5-chloro-4-(5-chloro-1H-pyrrolo-[2,3-b]pyridin-3-ylmethyl)-2-methoxy-phenoxymethyl]-1H-benzoimidazole

Participants

Reaction Conditions

Reaction Steps

[4-(1H-Benzoimidazol-2-ylmethoxy)-2-chloro-5-methoxy-phenyl]-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-methanol (138, 1.25 g, 0.00266 mol) was dissolved in acetonitrile (100 mL, 2 mol) and trifluoroacetic acid (5.65 mL, 0.0734 mol) and triethylsilane (11.3 mL, 0.0708 mol) were added. The reaction was heated at 70° C. for 2.5 hours. The reaction was concentrated and ethyl acetate and 1M aqueous potassium carbonate were added. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and filtered. The filtrate was adsorbed onto silica and purified with silica gel column chromatography, eluting with 0-8% methanol:dichloromethane to provide the desired compound as a solid, which was washed with a minimum of ethyl acetate and hexanes and filtered. The collected solid was dried to provide P-2104 (232 mg, 19%). MS (ESI) [M+H+]+=453.1, 455.1.

Provenance & Evidence