2-[4-(tert-Butyldimethylsilanyloxy)but-1-ynyl]phenylamine → 2-[2-(tert-Butyldimethylsilanyloxy)ethyl]-1H-indole

HRID 2264699

Reaktionsgleichung

Reaktionsgleichung von HRID 2264699
[Si:1]([O:8][CH2:9][CH2:10][C:11]#[C:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[NH2:19])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]>CN(C)C=O.[Cu]I>[Si:1]([O:8][CH2:9][CH2:10][C:11]1[NH:19][C:14]2[C:13]([CH:12]=1)=[CH:18][CH:17]=[CH:16][CH:15]=2)([C:4]([CH3:6])([CH3:7])[CH3:5])([CH3:3])[CH3:2]

Komponenten

4

Edukt 1

HCID 576757402-[4-(tert-Butyldimethylsilanyloxy)but-1-ynyl]phenylamine

Produkt 1

HCID 116088002-[2-(tert-Butyldimethylsilanyloxy)ethyl]-1H-indole

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

2-[4-(tert-Butyldimethylsilanyloxy)but-1-ynyl]phenylamine (8 mmol) was heated at reflux in N,N-dimethylformamide (30 mL) with copper(I) iodide (5 mg, 0.026 mmol) for 3 hours. The solvent was evaporated, and the residue was diluted with ether and filtered through Celite. The filtrate was concentrated, and the residue was purified by SiO2 chromatography (5-20% ethyl acetate/hexanes) to give the desired product, 0.88 g. 1H NMR (300 MHz, CDCl3) d 8.62 (br, 1H), 7.53 (d, J=7.5 Hz, 1H), 7.27 (d, J=7.8 Hz, 1H), 7.13-7.03 (m, 2H), 6.22 (s, 1H), 3.92 (t, J=5.7 Hz, 2H), 2.95 (t, J=5.7 Hz, 2H), 0.95 (s, 9H), 0.08 (s, 6H).

Aufarbeitung

  1. customThe solvent was evaporated
  2. additionthe residue was diluted with ether
  3. filtrationfiltered through Celite
  4. concentrationThe filtrate was concentrated
  5. customthe residue was purified by SiO2 chromatography (5-20% ethyl acetate/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-1d86fba72ba0425a9265d41083ecbd78
Quelldatensatz
uspto-grants-2010_12
Patentnummer
US07855224B2

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