Stannane, tributyl(1-methylethenyl)- → 2-(2-chloro-5-(prop-1-en-2-yl)pyridin-4-yl)-4-fluoro-1H-indole

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Reaction Steps

To a suspension of 6-chloro-4-(4-fluoro-1H-indol-2-yl)pyridin-3-yl trifluoromethanesulfonate (100 mg, 0.25 mmol) and tributyl(prop-1-en-2-yl)stannane (100 mg, 0.28 mmol) in DMF (2 mL) was added Pd(PPh3)4 (10 mg, 0.02 mmol) at 100° C. under N2, and the mixture was stirred for 5 hours. After concentrated in vacuum, the residue was suspended in H2O and extracted with EA. The combined organic layer was washed with H2O, brine, dried over Na2SO4, filtrated and concentrated to give 2-(2-chloro-5-(prop-1-en-2-yl)pyridin-4-yl)-4-fluoro-1H-indole (50 mg, yield: 70%). 1H-NMR (CDCl3, 400 MHz) δ 8.96 (s, 1H), 8.14 (s, 1H), 7.47 (s, 1H), 7.08˜7.13 (m, 2H), 6.95 (s, 1H), 6.72˜6.76 (m, 1H), 5.39 (s, 1H), 5.23 (s, 1H), 1.77 (s, 3H). MS (M+H)+: 287/289.

Provenance & Evidence