Tributylvinyltin → 2-(2-chloro-5-vinylpyridin-4-yl)-4-fluoro-1H-indole

Participants

Reaction Conditions

Reaction Steps

To a solution of 6-chloro-4-(4-fluoro-1H-indol-2-yl)pyridin-3-yl trifluoromethanesulfonate (50 mg, 0.12 mmol), LiCl (8 mg, 0.19 mmol) in DMF (0.8 mL) was added tributyl(vinyl)stannane (80 mg, 0.25 mmol) dropwise at 25° C. under nitrogen. The mixture was stirred at 65° C. for 10 hours. The mixture was diluted with H2O, extracted with EtOAc, then the combined organic phase was washed with brine, dried over Na2SO4 and concentrated in vacuo to give the crude product. It was purified by column (PE:EA=5:1) to obtain the product of 2-(2-chloro-5-vinylpyridin-4-yl)-4-fluoro-1H-indole (150 mg, yield: 40%). 1H-NMR (CDCl3, 400 MHz) δ 8.45 (s, 1H), 7.41 (s, 1H), 7.15 (d, J=2.4 Hz, 1H), 6.88 (d, J=6.0 Hz, 1H), 6.79 (t, J=6.0 Hz, 1H), 6.35˜6.41 (m, 1H), 6.07˜6.10 (m, 1H), 5.77 (d, J=17.6 Hz, 1H), 5.49˜5.62 (m, 2H). MS (M+H)+: 273/275.

Provenance & Evidence