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

HRID 595719Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 595719
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>CN(C=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=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]([C:27]([CH3:28])=[CH2:26])=[CH:8][N:9]=1

Komponenten

5

Edukt 2

HCID 10871254Stannane, tributyl(1-methylethenyl)-HCID 903335056-chloro-4-(4-fluoro-1H-indol-2-yl)pyridin-3-yl trifluoromethanesulfonate

Produkt 1

HCID 903338462-(2-chloro-5-(prop-1-en-2-yl)pyridin-4-yl)-4-fluoro-1H-indoleAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  1. concentrationAfter concentrated in vacuum
  2. extractionextracted with EA
  3. washThe combined organic layer was washed with H2O, brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltrated
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-447e3bc6923249ceb0e17ad812cb2dff
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09243002B2

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