Trifluoroacetic acid → HCID 86703323, compound

Participants

Reaction Steps

To a suspension of methyl 6-[hydroxyl(6-methoxy-2-pyrimidin-5-yl-1H-indol-3-yl)methyl]pyridine-2-carboxylate (828 mg) in dichloromethane (21.2 mL) was added triethylsilane (1.35 mL) under ice-cooling. Then trifluoroacetic acid (0.649 mL) was added dropwise thereto, and the mixture was stirred under ice-cooling for 30 minutes and then at room temperature for 1 hour. Triethylsilane (1.35 mL) and trifluoroacetic acid (0.649 mL) were added thereto, and the mixture was stirred at room temperature for additional 5 hours. The reaction mixture was diluted with ethyl acetate and washed with a saturated aqueous sodium hydrogen carbonate solution. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: methanol-ethyl acetate) to obtain the title compound (468 mg). 1H-NMR (CDCl3) δ ppm: 3.86 (3H, s), 4.03 (3H, s), 4.48 (2H, s), 6.80 (1H, dd, J=2.3, 8.8 Hz), 6.92 (1H, d, J=2.3 Hz), 7.23-7.28 (1H, m), 7.37 (1H, d, J=8.8 Hz), 7.64-7.71 (1H, m), 7.94-8.00 (1H, m), 8.16 (1H, br s), 9.04 (2H, s), 9.17 (1H, s). ESI-MS (m/z): 375 (M+H)+

Provenance & Evidence