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

HRID 595677

Reaktionsgleichung

FC(F)(F)S(O[C:7]1[CH:8]=[N:9][C:10]([Cl:23])=[CH:11][C:12]=1[C:13]1[NH:14][C:15]2[C:20]([CH:21]=1)=[C:19]([F:22])[CH:18]=[CH:17][CH:16]=2)(=O)=O.[CH2:26]([Sn](CCCC)(CCCC)/C=C\C)[CH2:27][CH2:28]C.[Li+].[Cl-]>CN(C=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:23][C:10]1[CH:11]=[C:12]([C:13]2[NH:14][C:15]3[C:20]([CH:21]=2)=[C:19]([F:22])[CH:18]=[CH:17][CH:16]=3)[C:7](/[CH:26]=[CH:27]\[CH3:28])=[CH:8][N:9]=1

Komponenten

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

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.

Aufarbeitung

additionwas added under N2 protection
filtrationThen it was filtered
concentrationconcentrated in vacuo
customThe residue was purified by column chromatography (PE:EA=10:1)

Quellen und Nachweise

ORD-Eintrag: ord-20987101a443457c87659a430f23ebe5
Quelldatensatz: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09243002B2

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