2-Fluoro-4-nitrophenol → 7-(2-Fluoro-4-nitrophenoxy)-2-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazol-4-yl)thieno[3,2-b]pyridine

HRID 1261226Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1261226
Cl[C:2]1[C:3]2[S:10][C:9]([C:11]3[N:12]=[CH:13][N:14]([CH2:16][O:17][CH2:18][CH2:19][Si:20]([CH3:23])([CH3:22])[CH3:21])[CH:15]=3)=[CH:8][C:4]=2[CH:5]=[CH:6][N:7]=1.C(=O)([O-])[O-].[K+].[K+].[F:30][C:31]1[CH:36]=[C:35]([N+:37]([O-:39])=[O:38])[CH:34]=[CH:33][C:32]=1[OH:40]>C1(OC2C=CC=CC=2)C=CC=CC=1.C(Cl)Cl>[F:30][C:31]1[CH:36]=[C:35]([N+:37]([O-:39])=[O:38])[CH:34]=[CH:33][C:32]=1[O:40][C:4]1[CH:5]=[CH:6][N:7]=[C:2]2[CH:8]=[C:9]([C:11]3[N:12]=[CH:13][N:14]([CH2:16][O:17][CH2:18][CH2:19][Si:20]([CH3:21])([CH3:22])[CH3:23])[CH:15]=3)[S:10][C:3]=12

Komponenten

6

Edukt 3

HCID 98252-Fluoro-4-nitrophenolHCID 11430Potassium CarbonateHCID 866445877-Chloro-2-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazol-4-yl)thieno[3,2-d]pyridine

Produkt 1

HCID 594245697-(2-Fluoro-4-nitrophenoxy)-2-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazol-4-yl)thieno[3,2-b]pyridineAusbeute 61 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 7583Diphenyl EtherLösungsmittel

Versuchsvorschrift

A suspension of 91 (4.2 g, 11.5 mmol), potassium carbonate (7.95 g, 57.5 mmol) and 2-fluoro-4-nitrophenol (4.97 g, 31.6 mmol) was heated at 190° C. in diphenyl ether (15 ml) for 4.5 hrs, cooled to room temperature, diluted with DCM and filtered. The filtrate was concentrated under reduced pressure and purified by column chromatography (eluents hexane and acetone/hexane, 45:55) to afford title compound 92 (3.4 mg, 61% yield) as a yellow solid MS (m/z) 487.0 (M+H).

Aufarbeitung

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. custompurified by column chromatography (eluents hexane and acetone/hexane, 45:55)

Quellen und Nachweise

ORD-Eintrag
ord-ea20d4f5152e4e55af08470d4a5e433a
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08470850B2

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