Potassium Carbonate → 5-[3-(4-Methyl-pyridin-3-yl)-2-oxo-imidazolidin-1-yl]-indole-1-carboxylic acid tert-butyl ester

HRID 80074

Reaktionsgleichung

Reaktionsgleichung von HRID 80074
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[N:8]1[CH2:12][CH2:11][NH:10][C:9]1=[O:13].[C:14]([O:18][C:19]([N:21]1[C:29]2[C:24](=[CH:25][C:26](Br)=[CH:27][CH:28]=2)[CH:23]=[CH:22]1)=[O:20])([CH3:17])([CH3:16])[CH3:15].N[C@@H]1CCCC[C@H]1N.C(=O)([O-])[O-].[K+].[K+]>[Cu](I)I.O1CCOCC1>[C:14]([O:18][C:19]([N:21]1[C:29]2[C:24](=[CH:25][C:26]([N:10]3[CH2:11][CH2:12][N:8]([C:3]4[CH:4]=[N:5][CH:6]=[CH:7][C:2]=4[CH3:1])[C:9]3=[O:13])=[CH:27][CH:28]=2)[CH:23]=[CH:22]1)=[O:20])([CH3:17])([CH3:15])[CH3:16]

Komponenten

7

Edukt 4

HCID 11430Potassium CarbonateHCID 438061,2-Diaminocyclohexane, trans-HCID 2728482N-Boc-5-bromoindoleHCID 596361701-(4-Methylpyridin-3-yl)imidazolidin-2-one

Produkt 1

HCID 687851905-[3-(4-Methyl-pyridin-3-yl)-2-oxo-imidazolidin-1-yl]-indole-1-carboxylic acid tert-butyl esterAusbeute 24 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 83717Copper iodideKatalysatorHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

Using the same reaction conditions as in Example 14, 1-(4-methyl-pyridin-3-yl)-imidazolidin-2-one (I-14b: 250 mg, 1.412 mmol) was reacted with 5-bromo-indole-1-carboxylic acid tert-butyl ester (0.499 g, 1.691 mmol), 1,4-dioxane (15 mL), copper iodide (0.0080 g), trans-1,2-diamino cyclohexane (0.0241 g, 0.2110 mmol) and potassium carbonate (0.389 g, 2.818 mmol) to afford the crude product. Purification by column chromatography on silica gel (10% MeOH in CHCl3) afforded 125 mg of 5-[3-(4-Methyl-pyridin-3-yl)-2-oxo-imidazolidin-1-yl]-indole-1-carboxylic acid tert-butyl ester (24% yield).

Aufarbeitung

  1. customto afford the crude product
  2. customPurification by column chromatography on silica gel (10% MeOH in CHCl3)

Quellen und Nachweise

ORD-Eintrag
ord-17c99190785f45c1b4290667a3de1651
Quelldatensatz
uspto-grants-2014_09
Patentnummer
USRE045173E1

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