Tetrabutylammonium Fluoride → HCID 46186188, compound

Participants

Reaction Steps

At room temperature and under inert atmosphere, 1.0 M TBAF in THF (310 μL, 5 equiv.) was added a solution of 17 (30 mg, 0.061 mmol) in anhydrous THF (2.5 mL). The solution was refluxed for 2 h. The resulting mixture was then cautiously quenched at 0° C. with H2O. The mixture was extracted with EtOAc (3×10 mL). The resulting organic layers were dried over MgSO4, filtered, and solvents were removed under reduced pressure. The crude product was purified by flash chromatography (EtOAc) to afford R265 in 61% yield. 1H-NMR (300 MHz, DMSO-d6): δ 11.91 (bs, 1H), 8.65 (d, 1H, J=2.3 Hz), 8.61 (bt, 1H, J=5.5 Hz), 8.39 (d, 1H, J=2.3 Hz), 8.07 (bs, 1H), 7.82 (d, 1H, J=7.5 Hz), 7.54-7.37 (m, 5H), 3.55 (q, 2H, J=7.7 Hz), 2.98 (t, 2H, J=7.7 Hz); MS (ESI) m/z 350.2 [M+H+], 698.9 [2M+H+], 721.0 [2M+Na+], HRMS (ESI): Calcd for C20H16ClN3O: 350.1060. Found: 350.10631.

Provenance & Evidence