Pyrrolidine → HCID 24957616, compound

Participants

Reaction Steps

A mixture of 0.1 g (0.18 mmol) of 1-(1-allyl-6-bromo-1H-indol-3-yl)-2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]ethanol, 28.0 mg (0.4 mmol) of pyrrolidine, 5.0 mg of Pd catalyst (prepared according to a procedure described in Org. Lett. 2003 14 2413-2415), and 35.0 mg (0.36 mmol) of sodium tert-butoxide in 10 mL of dioxane was warmed at 90° C. After 2 hours, the mixture was cooled to room temperature, filtered through CELITE® filter aid, diluted with water, and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by flash chromatography using ethyl acetate in hexanes (30-80% gradient). The major fractions were combined and concentrated in vacuo to afford 21.0 mg 21.4%) of the title compound. MS m/z 534.5 (MH+).

Provenance & Evidence