Hydrochloric Acid → HCID 67314433, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 5-fluoro-1,3-dihydro-indol-2-one (143 mg, 0.95 mmol) in THF (4 mL) at room temperature is treated with lithium bis(trimethylsilyl)amide (1.0 M solution in tetrahydrofuran, 2.2 mL, 2.2 mmol) and stirred for 10 min. A solution of 2-(3-{4-[2-(2-Hydroxy-ethoxy)-ethyl]-piperazin-1-yl}-propyl)-7H-furo[3,4-b]pyridin-5-one (110 mg, 0.31 mmol) in anhydrous THF (2 mL) is added. The reaction mixture is stirred at room temperature for 2 h. The reaction mixture is poured into aqueous 2N HCl (10 mL) with stirring and is heated at 60° C. for 2.5 h. The mixture is then poured into 100 mL ice water, to which solid NaHCO3 is carefully added to adjust pH to 8. The aqueous layer is extracted with chloroform (3×). The combined organic layers are dried with anhydrous Na2SO4, and concentrated. The residue purified by column chromatography (MeOH-chloroform) to give the title compound as a yellow solid (51 mg, 34%).

Provenance & Evidence