Water → 5-(2,6-Diethyl-Phenyl)-1-(1-Propyl-Butyl)-1H-Pyrrolo[2,3-C]Pyridine

HRID 472021Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 472021
[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][CH3:10])[C:4]=1[C:11]1[CH:12]=[C:13]2[CH:19]=[CH:18][NH:17][C:14]2=[CH:15][N:16]=1)[CH3:2].[H-].[Na+].Br[CH:23]([CH2:27][CH2:28][CH3:29])[CH2:24][CH2:25][CH3:26].O>CN(C=O)C.CCOC(C)=O>[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][CH3:10])[C:4]=1[C:11]1[CH:12]=[C:13]2[CH:19]=[CH:18][N:17]([CH:23]([CH2:27][CH2:28][CH3:29])[CH2:24][CH2:25][CH3:26])[C:14]2=[CH:15][N:16]=1)[CH3:2]

Komponenten

7

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 704604-BromoheptaneHCID 116732465-(2,6-diethyl-phenyl)-1H-pyrrolo[2,3-c]pyridine

Produkt 1

HCID 116817955-(2,6-Diethyl-Phenyl)-1-(1-Propyl-Butyl)-1H-Pyrrolo[2,3-C]Pyridine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 5-(2,6-diethyl-phenyl)-1H-pyrrolo[2,3-c]pyridine (32 mg, 0.13 mmol) in DMF (0.5 mL) is added NaH (95%, 6 mg). The reaction mixture is stirred at room temperature for 30 minutes, and 4-bromo-heptane (137 mg, 0.77 mmol) is added. The mixture is heated at 60° C. for three hours and cooled. To the mixture, water (2 mL) and EtOAc (2 mL) are added. The organic layer is separated, washed with water once and concentrated under reduced pressure. The residue is purified by PTLC (Hexane/EtOAc 4:1) to give the titled compound. 1H NMR: (CDCl3) 8.82 (s, 1H), 7.43 (s, 1H), 7.32 (d, 1H), 7.31 (t, 1H), 7.16 (d, 2H), 6.87 (s, 1H), 6.53 (d, 1H), 4.42 (m, 1H), 2.32-2.40 (m, 4H), 1.86-1.95 (m, 4H), 1.15-1.32 (m, 4H), 1.03 (t, 6H), 0.84 (m, 6H).

Aufarbeitung

  1. temperatureThe mixture is heated at 60° C. for three hours
  2. temperaturecooled
  3. customThe organic layer is separated
  4. washwashed with water once
  5. concentrationconcentrated under reduced pressure
  6. customThe residue is purified by PTLC (Hexane/EtOAc 4:1)

Quellen und Nachweise

ORD-Eintrag
ord-b23f2140518446078bc89404aca994c1
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08633193B2

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