2-Fluoro-4-nitrophenol → 7-(2-fluoro-4-nitrophenoxy)-1H-pyrrolo[3,2-b]pyridine

HRID 1711041Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1711041
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[CH:9][NH:10][C:3]=12.[F:11][C:12]1[CH:17]=[C:16]([N+:18]([O-:20])=[O:19])[CH:15]=[CH:14][C:13]=1[OH:21].C([O-])([O-])=O.[K+].[K+]>O(C1C=CC=CC=1)C1C=CC=CC=1>[F:11][C:12]1[CH:17]=[C:16]([N+:18]([O-:20])=[O:19])[CH:15]=[CH:14][C:13]=1[O:21][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[CH:9][NH:10][C:3]=12

Komponenten

5

Edukt 3

HCID 98252-Fluoro-4-nitrophenolHCID 11430Potassium CarbonateHCID 224762367-Chloro-1H-pyrrolo[3,2-b]pyridine

Produkt 1

HCID 594245967-(2-fluoro-4-nitrophenoxy)-1H-pyrrolo[3,2-b]pyridineAusbeute 26,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7583Diphenyl EtherLösungsmittel

Reaktionsbedingungen

Temperatur
170 °C

Versuchsvorschrift

A mixture of 266 (180 mg, 1.18 mmol), 2-fluoro-4-nitrophenol (558 mg, 3.55 mmol) and K2CO3(981 mg, 7.10 mmol) in Ph2O (4 mL) was heated at 170° C. for 8 hours, cooled to room temperature and partitioned between EtOAc and water. Organic phase was collected, dried over anhydrous Na2SO4 and concentrated. The residue was purified by flash column chromatography with gradient elution of hexane, to hexane/EtOAc (1:1), to afford the title compound 267 (84 mg, 26% yield) as a yellowish solid. MS (m/z): 274. 1 (M+H) (found).

Aufarbeitung

  1. temperaturecooled to room temperature
  2. custompartitioned between EtOAc and water
  3. customOrganic phase was collected
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified by flash column chromatography with gradient elution of hexane, to hexane/EtOAc (1:1)

Quellen und Nachweise

ORD-Eintrag
ord-27113b4ced774d86ad8e1ba7fbd4eb33
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07790729B2

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