Imidazole → 6-imidazol-1-yl-1-methyl-1H-indole

HRID 651753

Reaktionsgleichung

Reaktionsgleichung von HRID 651753
N1[C:14]2[C:5](=[CH:6][CH:7]=[C:8]3[C:13]=2[N:12]=[CH:11][CH:10]=[CH:9]3)C=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+].[NH:39]1[CH:43]=[CH:42][N:41]=[CH:40]1.IC1C=C2C(C=CN2C)=CC=1>C1(C)C(C)=CC=CC=1>[N:39]1([C:5]2[CH:14]=[C:13]3[C:8]([CH:9]=[CH:10][N:12]3[CH3:11])=[CH:7][CH:6]=2)[CH:43]=[CH:42][N:41]=[CH:40]1

Komponenten

7

Edukt 5

HCID 795ImidazoleHCID 13181,10-PhenanthrolineHCID 10796Cesium carbonateHCID 95417Dibenzylidene acetoneHCID 217090906-iodo-1-methyl-1H-indole

Produkt 1

HCID 217090586-imidazol-1-yl-1-methyl-1H-indoleAusbeute 50 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7237O-XyleneLösungsmittel

Reaktionsbedingungen

Temperatur
160 °C

Versuchsvorschrift

An oven-dried re-sealable Schlenk tube was flushed with argon and charged with copper(I) trifluoromethanesulfonate benzene complex (1.39 g, 2.76 mmol), 1.10-phenanthroline (5.69 g, 31.6 mmol), dibenzylideneacetone (740 mg, 3.16 mmol) and cesium carbonate (10 g, 30.7 mmol). Imidazole (3.23 g 44.8 mmol), 6-iodo-1-methyl-1H-indole (8.13 g, 31.6 mmol) and xylene (16 mL) were added and the tube was purged with argon. The tube was sealed and heated with stirring at 160° C. for 18 h. The mixture was cooled to room temperature and partitioned between CH2Cl2 (35 mL) and saturated aqueous NH4Cl (5 mL). The organic layer was separated and washed with brine. Then the organic extract was dried over MgSO4, filtered and concentrated. The crude concentrate was filtered though a pad of silica gel and evaporated. Purification by HPLC afforded 6-imidazol-1-yl-1-methyl-1H-indole as a brown oil (3.1 g, 50%). [Ref: Kiyoori, A.; Marcoux, J-F.; Buchwald, S. L. Tetrahedron Lett., 1999, 40, 2657.]

Aufarbeitung

  1. customAn oven-dried re-sealable Schlenk tube was flushed with argon
  2. customthe tube was purged with argon
  3. customThe tube was sealed
  4. temperatureheated
  5. temperatureThe mixture was cooled to room temperature
  6. custompartitioned between CH2Cl2 (35 mL) and saturated aqueous NH4Cl (5 mL)
  7. customThe organic layer was separated
  8. washwashed with brine
  9. extractionThen the organic extract
  10. dry with materialwas dried over MgSO4
  11. filtrationfiltered
  12. concentrationconcentrated
  13. concentrationThe crude concentrate
  14. filtrationwas filtered though a pad of silica gel
  15. customevaporated
  16. customPurification by HPLC

Quellen und Nachweise

ORD-Eintrag
ord-4198fa67f8cb4607a40ddde624c8115e
Quelldatensatz
uspto-grants-2001_08
Patentnummer
US06281356B1

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