Cesium fluoride → HCID 86728250, Verbindung

HRID 1776843Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1776843
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([C:9]2[NH:10][C:11]3[C:16]([CH:17]=2)=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH:3]=1.[F-].[Cs+].[N+](C1C=C(S(O[CH2:33][CH:34]2[CH2:36][O:35]2)(=O)=O)C=CC=1)([O-])=O>CN(C=O)C.C(OCC)(=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:33][CH:34]2[CH2:36][O:35]2)=[C:4]([C:9]2[NH:10][C:11]3[C:16]([CH:17]=2)=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH:3]=1

Komponenten

6

Edukt 3

HCID 25953Cesium fluorideHCID 286836(Oxiran-2-yl)methyl 3-nitrobenzene-1-sulfonateHCID 13163448HCID 13163448, Verbindung

Produkt 1

HCID 86728250HCID 86728250, VerbindungAusbeute 84 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of compound 4-bromo-2-(1H-indol-2-yl)phenol (1 g, 3.48 mmol) in DMF (35 mL) was added CsF (1.59 g, 10.45 mmol) and oxiran-2-ylmethyl 3-nitrobenzenesulfonate (1.81 g, 6.97 mmol). The resulting mixture was stirred at room temperature overnight and then diluted with ethyl acetate and washed with water and brine. The crude product was purified using chromatography (petroleum ether:EA=14:1) to provide compound 2-(5-bromo-2-(oxiran-2-ylmethoxy)phenyl)-1H-indole (1 g, yield: 84.0%). 1H-NMR (DMSO-d6, 400 MHz) δ 11.33 (s, 1H), 7.96 (d, J=2.4 Hz, 1H), 7.51 (d, J=7.6 Hz, 1H), 7.38˜7.44 (m, 2H), 7.07˜7.12 (m, 3H), 6.97 (t, J=7.2 Hz, 1H), 4.49˜4.53 (m, 1H), 3.97˜4.01 (m, 1H), 3.46˜3.49 (m, 1H), 2.88 (t, J=4.4 Hz, 1H), 2.74˜2.76 (m, 1H). MS (M+H)+: 344/346.

Aufarbeitung

  1. washwashed with water and brine
  2. customThe crude product was purified

Quellen und Nachweise

ORD-Eintrag
ord-11acd117b9b04d6fa7ef1b971816b4a5
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09265773B2

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