2-(pyridin-3-yl)-1H-indole → 3-[2-(4-Ethoxycarbonylphenoxy)ethyl]-2-(3-pyridyl)-indole

HRID 1980859Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1980859
C([Mg]Br)C.[N:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]2[NH:12][C:13]3[C:18]([CH:19]=2)=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH:6]=1.Br[CH2:21][CH2:22][O:23][C:24]1[CH:34]=[CH:33][C:27]([C:28]([O:30][CH2:31][CH3:32])=[O:29])=[CH:26][CH:25]=1>O1CCCC1>[CH2:31]([O:30][C:28]([C:27]1[CH:33]=[CH:34][C:24]([O:23][CH2:22][CH2:21][C:19]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[NH:12][C:11]=2[C:7]2[CH:6]=[N:5][CH:10]=[CH:9][CH:8]=2)=[CH:25][CH:26]=1)=[O:29])[CH3:32]

Komponenten

5

Edukt 3

HCID 6066772-(pyridin-3-yl)-1H-indoleHCID 12708668Ethyl 4-(2-bromoethoxy)benzoateHCID 178418443HCID 178418443, Verbindung

Produkt 1

HCID 204007903-[2-(4-Ethoxycarbonylphenoxy)ethyl]-2-(3-pyridyl)-indole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel3×

Versuchsvorschrift

To 12.0 ml of a 2M solution of ethylmagnesium bromide in tetrahydrofuran under nitrogen at 0°-5° is added dropwise over 20 minutes a solution of 4.0 g of 2-(3-pyridyl)indole in 20 ml of tetrahydrofuran. The mixture is stirred for 0.5 hours at 0°-5° and then is added a solution of 5.06 g of ethyl p-(2-bromoethoxy)benzoate [for preparation see U.S. Pat. No. 2,790,825 (1957)] in 30 ml of tetrahydrofuran. The suspension is stirred at 0°-10° for 1 hour and at room temperature for 0.5 hour, poured into ice-water and extracted with ether. The ether extract is separated, dried over MgSO4, and concentrated to give 3-[2-(4-ethoxycarbonylphenoxy)-ethyl]-2-(3-pyridyl)-indole.

Aufarbeitung

  1. customfor preparation
  2. stirringThe suspension is stirred at 0°-10° for 1 hour and at room temperature for 0.5 hour
  3. extractionextracted with ether
  4. extractionThe ether extract
  5. customis separated
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-135efbcacef84bd1a9f20aea46b9162b
Quelldatensatz
uspto-grants-1985_04
Patentnummer
US04511573

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