Isopropyltriphenylphosphonium iodide → 2-(2-chloro-5-(2-methylprop-1-en-1-yl)pyridin-4-yl)-4-fluoro-1H-indole

Participants

Reaction Conditions

Reaction Steps

n-BuLi (3.15 mL, 7.88 mmol, 2.5 M in hexane) was added dropwise to a mixture of isopropyltriphenylphosphonium iodide (3.55 g, 8.21 mmol) in THF (30 mL) at −78° C. under N2 atmosphere. The mixture was stirred at −78° C. for 1 hour. Then a solution of 6-chloro-4-(4-fluoro-1H-indol-2-yl)nicotinaldehyde (900 mg, 3.28 mmol) in THF (10 mL) was added dropwise to the mixture at −78° C. The mixture was stirred at room temperature overnight. The mixture was then diluted with water (100 mL) and extracted with EA (50 mL*3). The organic layer was washed with brine (50 mL), dried over Na2SO4 and concentrated. The residue was purified by column chromatography (PE:EA=4:1) to give the product of 2-(2-chloro-5-(2-methylprop-1-en-1-yl)pyridin-4-yl)-4-fluoro-1H-indole (500 mg, yield: 50.6%). 1H-NMR (CDCl3, 400 MHz) δ 8.66 (br s, 1H), 8.17 (s, 1H), 7.51 (s, 1H), 7.12 (br s, 2H), 6.96 (d, J=1.6 Hz, 1H), 6.70˜6.81 (m, 1H), 6.22 (br s, 1H), 1.97 (s, 3H), 1.68˜1.70 (m, 1H), 1.74 (s, 3H). MS (M+H)+: 301/303.

Provenance & Evidence