Acetonitrile → 2-[4-(5-Chloro-1H-pyrrolo[2, 3-b]pyridin-3-ylmethyl)-5-fluoro-2-methoxy-phenoxymethyl]-1-methyl-1H-benzimidazole

Participants

Reaction Conditions

Reaction Steps

(5-Chloro-1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-[2-fluoro-5-methoxy-4-(1-methyl-1H-benzimidazol-2-ylmethoxy)-phenyl]-methanol (145) (0.140 g, 0.225 mmol) was suspended in acetonitrile (5 ml, 100 mmol). Triethylsilane (1.0 mL, 6.3 mmol) was added followed by trifluoroacetic acid (0.500 mL, 6.4 mmol). After the reaction was stirred at 60-80° C. for 1.5 hours the solvent was evaporated to dryness. Ethyl acetate was added and the organic portion was washed with saturated sodium bicarbonate solution and brine, dried over anhydrous sodium sulfate and concentrated. Purification with silica gel flash chromatography eluting with a gradient of ethyl acetate (20 to 100%) in hexanes gave the desired compound as a white powder (P-2106, 0.034 g, 34%). MS (ESI) [M+H+]+=451.2.

Provenance & Evidence