Tetrabutylammonium Fluoride → HCID 86703321, compound

Participants

Reaction Steps

tert-Butyl 6-methoxy-2-pyrimidin-5-yl-1H-indole-1-carboxylate (295 mg) in tetrahydrofuran (2.27 mL) was added tetrabutylammonium fluoride (about 1.0 mol/L tetrahydrofuran solution, 3.63 mL) at room temperature, and the mixture was heated under reflux for 30 hours. The reaction mixture was left to be cooled, diluted with ethyl acetate, and then washed with saturated brine. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane) to obtain the title compound (186 mg). 1H-NMR (CDCl3) δ ppm: 3.88 (3H, s), 6.84 (1H, dd, J=2.3, 8.8 Hz), 6.88-6.95 (2H, m), 7.54 (1H, d, J=8.8 Hz), 8.20-8.52 (1H, br), 8.99 (2H, s), 9.11 (1H, s). ESI-MS (m/z): 226 (M+H)+

Provenance & Evidence