Triethylamine → perfluorophenyl 3-bromo-1-methyl-1H-indole-6-sulfonate

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[Br:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([S:11](Cl)(=[O:13])=[O:12])=[CH:8][CH:9]=2)[N:4]([CH3:15])[CH:3]=1.[F:16][C:17]1[C:22]([OH:23])=[C:21]([F:24])[C:20]([F:25])=[C:19]([F:26])[C:18]=1[F:27].C(N(CC)CC)C>C(Cl)Cl>[Br:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([S:11]([O:23][C:22]3[C:21]([F:24])=[C:20]([F:25])[C:19]([F:26])=[C:18]([F:27])[C:17]=3[F:16])(=[O:13])=[O:12])=[CH:8][CH:9]=2)[N:4]([CH3:15])[CH:3]=1

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실험 절차

A vial was charged with 3-bromo-1-methyl-1H-indole-6-sulfonyl chloride (505.0 mg, 1.637 mmol), pentafluorophenol (452 mg, 2.455 mmol), and DCM (8.1 mL) to give a clear, light-yellow solution. Triethylamine (342 μl, 2.455 mmol) was added dropwise, and the resulting mixture was stirred for 45 min before being concentrated in vacuo. The crude product was purified by chromatography on silica gel (40% EtOAc/Heptane) to give perfluorophenyl 3-bromo-1-methyl-1H-indole-6-sulfonate (712.3 mg, 1.561 mmol, 95% yield) as an off-white solid. 1H NMR (400 MHz, CHLOROFORM-d) δ=8.04 (t, J=1.1 Hz, 1 H), 7.82-7.67 (m, 2 H), 7.41 (s, 1 H), 3.91 (s, 3 H).