Ethyl Acetate → HCID 21835209, Verbindung

HRID 1741275

Reaktionsgleichung

[N:1]1[N:2]=[CH:3][N:4]([C:6]2[CH:7]=[C:8]3[C:12](=[CH:13][CH:14]=2)[NH:11][CH:10]=[C:9]3[CH2:15][CH2:16][CH2:17][CH:18]2[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]2)[CH:5]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH:31]([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[C:32]([O:34][CH3:35])=[O:33].C(OCC)(=O)C>CN(C=O)C.O>[N:1]1[N:2]=[CH:3][N:4]([C:6]2[CH:7]=[C:8]3[C:12](=[CH:13][CH:14]=2)[NH:11][CH:10]=[C:9]3[CH2:15][CH2:16][CH2:17][CH:18]2[CH2:23][CH2:22][N:21]([CH:31]([C:32]([O:34][CH3:35])=[O:33])[C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[CH2:20][CH2:19]2)[CH:5]=1

Komponenten

Reaktionsbedingungen

Temperatur: 25 °C

Versuchsvorschrift

4-[3-(5-(1,2,4-Triazol-4-yl)-1H-indol-3-yl)propyl]piperidine (Description 2, 0.800 g, 0.0026 mol) was dissolved in anhydrous DMF (10 ml), under N2, and potassium carbonate (0.540 g, 0.0039 mol) added followed by (±)-methyl α-bromophenylacetate (Aldrich, 0.5 ml, 0.0031 mol). The reaction was stirred at 25° C. for 16 h, then poured into ethyl acetate (100 ml) and H2O (30 ml). The organic layer was collected, washed with H2O (3×30 ml), dried over MgSO4 and evaporated with 1-5% MeOH/CH2Cl2 to obtain the title compound as a colourless oil. 1H NMR 1.23-1.33 (6H, m), 1.66 (5H, m), 2.04 (1H, br m), 2.72 (2H, t, J=3 Hz), 2.96 (1H, bm), 3.69 (3H, s), 3.98 (1H, br s), 7.11 (1H, d, J=1 Hz), 7.14 (1H, d, J=2 Hz), 7.33 (3H, m), 7.43-7.48 (2H, m), 7.50 (1H, d, J=3 Hz), 7.51 (1H, d, J=1 Hz), 8.07 (br s, indole (NH)), 8.45 (2H, s, Ar (triazole)).

Aufarbeitung

customThe organic layer was collected
washwashed with H2O (3×30 ml)
dry with materialdried over MgSO4
customevaporated with 1-5% MeOH/CH2Cl2

Quellen und Nachweise

ORD-Eintrag: ord-7643b46c4e9447ef9e96d0557779fd3c
Quelldatensatz: uspto-grants-1999_10
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05973156

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