5-Bromoindole → 4-(1H-Indol-5-yl)-butyronitrile

HRID 24038

Reaktionsgleichung

Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.[Br-].[C:12]([CH2:14][CH2:15][CH2:16][Zn+])#[N:13]>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>[NH:7]1[C:8]2[C:4](=[CH:3][C:2]([CH2:16][CH2:15][CH2:14][C:12]#[N:13])=[CH:10][CH:9]=2)[CH:5]=[CH:6]1

Komponenten

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

A mixture of 5-bromoindole (0.25 g, 1.25 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.10 g, 0.12 mmol) was stirred under a nitrogen atmosphere for 10 minutes. 3-cyanopropyl zinc bromide [0.5 M in THF] (5.0 mL, 2.50 mmol) was added to the mixture and heated in the microwave at 100° C. for 15 minutes. The solvent was removed and the crude mixture was purified via column chromatography with silica gel, eluting with hexane/ethyl acetate (4/1) to afford the title compound in 63% yield. 1H NMR (CDCl3) δ 8.22 (br, 1H), 7.43 (s, 1H), 7.31 (d, J=8.3 Hz, 1H), 7.18 (s, 1H), 7.00 (d, J=8.3 Hz, 1H), 6.49 (s, 1H), 2.86 (t, J=7.3 Hz, 2H), 2.28 (t, J=7.2 Hz, 2H), 2.02 (m, 2H). Mass Spectrum (LCMS, ESI) calculated for C12H13N2 185.1 (M+H); found 185.1.

Aufarbeitung

customThe solvent was removed
customthe crude mixture was purified via column chromatography with silica gel
washeluting with hexane/ethyl acetate (4/1)

Quellen und Nachweise

ORD-Eintrag: ord-7f004eb4a9904704a1ece903785d0a07
Quelldatensatz: uspto-grants-2005_02
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06855722B2

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