8-Quinolinecarboxaldehyde → quinolin-8-yl(1-trityl-1H-imidazol-5-yl)methanol

HRID 390360Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 390360
I[C:2]1[N:3]=[CH:4][N:5]([C:7]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=1.C([Mg]Br)C.[N:30]1[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][C:38]=2[CH:40]=[O:41])[CH:33]=[CH:32][CH:31]=1>ClCCl>[N:30]1[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][C:38]=2[CH:40]([C:6]2[N:5]([C:7]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)([C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=3)[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH:4]=[N:3][CH:2]=2)[OH:41])[CH:33]=[CH:32][CH:31]=1

Komponenten

5

Edukt 3

HCID 1701038-QuinolinecarboxaldehydeHCID 6182524-Iodo-1-tritylimidazoleHCID 178418443HCID 178418443, Verbindung

Produkt 1

HCID 59419662quinolin-8-yl(1-trityl-1H-imidazol-5-yl)methanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A solution of 4-iodo-1-tritylimidazole (commercially available) 5.2 g, 11.94 mmol) in dichloromethane (80 mL) at −10° C. was treated with ethyl magnesium bromide (3.98 mL, 11.94 mmol, 3M in ether) and allowed to react for 45 m. A solution of quinoline-8-carbaldehyde, (Intermediate 11) (1.5 g, 9.55 mmol) in dichloromethane was added via syringe at −10° C. and stirred for 16 h at room temperature. The mixture was quenched with water (50 mL) and a sat. solution of ammonium chloride (50 mL) and subjected to an aqueous work-up. The residue was purified by chromatography on silica gel with 3% NH3-MeOH: CH2Cl2 to give to give quinolin-8-yl(1-trityl-1H-imidazol-5-yl)methanol, (Intermediate 12) as a solid, (3.7 g 82.7%).

Aufarbeitung

  1. customto react for 45 m
  2. customThe mixture was quenched with water (50 mL)
  3. customThe residue was purified by chromatography on silica gel with 3% NH3-MeOH
  4. customCH2Cl2 to give

Quellen und Nachweise

ORD-Eintrag
ord-5460970c91f141c7910fe67f9d2b2fc5
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08383646B2

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