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

HRID 1261336Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1261336
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-4c1ba572de734e8380ad1fa36353fc58
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08470850B2

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