Trifluoroacetic acid → HCID 59803827, compound

Participants

Reaction Steps

(4-Benzyloxy-2-fluoro-5-methoxy-phenyl)-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-methanol 223a and 3-[(4-benzyloxy-2-fluoro-5-methoxy-phenyl)-methoxy-methyl]-5-chloro-1H-pyrrolo[2,3-b]pyridine 223b (48 mmol) were combined with acetonitrile (1.4 L), trifluoroacetic acid (21 mL, 288 mmol) and triethylsilane (31 mL, 192 mmol). The resulting mixture was stirred for two hours at reflux. The solvent was removed under reduced pressure. Ethyl acetate (6 L) was added and the organic layer was washed with aqueous potassium carbonate saturated solution. The layers were separated and the aqueous layer was back-extracted with ethyl acetate (2 L). The combined organic portions were dried over anhydrous sodium sulfate and evaporated under reduced pressure to give the desired compound 224 which was used without further purification.

Provenance & Evidence