Reaktion #682859

Reaktionsgleichung

6-chloro-4-(4-fluoro-1H-indol-2-yl)pyridin-3-yl trifluoromethanesulfonate

(Z)-tributyl (prop-1-en-1-yl) stannane

LiCl

→

(Z)-2-(2-chloro-5-(prop-1-en-1-yl)pyridin-4-yl)-4-fluoro-1H-indole

Ausbeute 61.9%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added under N2 protection
2. 2
   FiltrationThen it was filtered
3. 3
   Einengenconcentrated in vacuo
4. 4
   SonstigeThe residue was purified by column chromatography (PE:EA=10:1)

Vorschrift

To a mixture of 6-chloro-4-(4-fluoro-1H-indol-2-yl)pyridin-3-yl trifluoromethanesulfonate (200 mg, 0.51 mmol), (Z)-tributyl (prop-1-en-1-yl) stannane (170 mg, 0.51 mmol) and anhydrous LiCl (70 mg, 1.65 mmol) in DMF (2 mL), Pd(PPh3)2Cl2 (30 mg, 0.04 mmol) was added under N2 protection. The reaction mixture was stirred at 100° C. for 10 h. Then it was filtered and concentrated in vacuo. The residue was purified by column chromatography (PE:EA=10:1) to give the product of (Z)-2-(2-chloro-5-(prop-1-en-1-yl)pyridin-4-yl)-4-fluoro-1H-indole (90 mg, yield: 61.9%). 1H-NMR (CDCl3, 400 MHz) δ 12.02 (br s, 1H), 8.33 (s, 1H), 7.87 (s, 1H), 7.31 (d, J=7.6 Hz, 1H), 7.16˜7.21 (m, 1H), 6.98 (d, J=1.2 Hz, 1H), 6.85 (dd, J=10.8, 7.6 Hz, 1H), 6.57 (dd, J=11.2, 1.6 Hz, 1H), 6.06˜6.16 (m, 1H), 1.78 (dd, J=6.8, 1.6 Hz, 3H). MS (M+H)+: 287.

Quelle