Methyl 4-(bromomethyl)-3-methoxybenzoate → Methyl 4-[1-(2-carbamoylethyl)-5-(N-cyclopentylmethylcarbamoyl)indol-3-ylmethyl]-3-methoxybenzoate

HRID 728673

Reaktionsgleichung

Reaktionsgleichung von HRID 728673
[C:1]([CH2:4][CH2:5][N:6]1[C:14]2[C:9](=[CH:10][C:11]([C:15](=[O:23])[NH:16][CH2:17][CH:18]3[CH2:22][CH2:21][CH2:20][CH2:19]3)=[CH:12][CH:13]=2)[CH:8]=[CH:7]1)(=[O:3])[NH2:2].Br[CH2:25][C:26]1[CH:35]=[CH:34][C:29]([C:30]([O:32][CH3:33])=[O:31])=[CH:28][C:27]=1[O:36][CH3:37]>O1CCOCC1.C(OCC)(=O)C.[Ag-]=O>[C:1]([CH2:4][CH2:5][N:6]1[C:14]2[C:9](=[CH:10][C:11]([C:15](=[O:23])[NH:16][CH2:17][CH:18]3[CH2:22][CH2:21][CH2:20][CH2:19]3)=[CH:12][CH:13]=2)[C:8]([CH2:25][C:26]2[CH:35]=[CH:34][C:29]([C:30]([O:32][CH3:33])=[O:31])=[CH:28][C:27]=2[O:36][CH3:37])=[CH:7]1)(=[O:3])[NH2:2]

Komponenten

6

Edukt 2

HCID 2759828Methyl 4-(bromomethyl)-3-methoxybenzoateHCID 198224771-(2-carbamoylethyl)-5-(N-cyclopentylmethylcarbamoyl)indole

Produkt 1

HCID 19822473Methyl 4-[1-(2-carbamoylethyl)-5-(N-cyclopentylmethylcarbamoyl)indol-3-ylmethyl]-3-methoxybenzoateAusbeute 39 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418778HCID 178418778, VerbindungKatalysatorHCID 8857Ethyl AcetateLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Silver(I) oxide (0.17 g) was added to a solution of 1-(2-carbamoylethyl)-5-(N-cyclopentylmethylcarbamoyl)indole (0.70 g) and methyl 4-bromomethyl-3-methoxybenzoate (B)(0.19 g) in 1,4-dioxane (10 ml). The mixture was protected from light and stirred at 80° C. under an atmosphere of nitrogen for 12 hours. The mixture was then diluted with 1:1 v/v ethyl acetate:ether (50 ml) and filtered. The filtrate was washed sequentially with water and brine, dried (MgSO4), and evaporated. The residual yellow gum was purified by flash chromatography on silica gel (500 ml), eluting with 5:95 v/v methanol:chloroform to give the title compound (0.14 g, 39%) as a white solid; mp 189°-191° C. (d); NMR (250 MHz, DMSO-d6): 1.2-1.8(broad m, 8H, cyclopentyl), 2.2(sep, 1H, cyclopentylmethine), 3.2(t, 2H, CH2NH), 7.2(m, 2H), 7.3(broad s, 1H, CONH2), 7.5 (m, 3H), 7.7(d, 1H, H6 -indole), 8.0(s, 1H, H4 -indole), 8.3(t, 1H, NHCO).

Aufarbeitung

  1. filtrationether (50 ml) and filtered
  2. washThe filtrate was washed sequentially with water and brine
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customThe residual yellow gum was purified by flash chromatography on silica gel (500 ml)
  6. washeluting with 5:95 v/v methanol

Quellen und Nachweise

ORD-Eintrag
ord-52361734dd5344259ca8db06edd05715
Quelldatensatz
uspto-grants-1991_09
Patentnummer
US05049679

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