Potassium Carbonate → HCID 21049421, Verbindung

HRID 222051

Reaktionsgleichung

Reaktionsgleichung von HRID 222051
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][N:8]=[CH:7]2)([O-:3])=[O:2].[F:13][C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=1)[CH2:17]Br.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH2:17][C:16]1[CH:19]=[CH:20][CH:21]=[C:14]([F:13])[CH:15]=1)[N:8]=[CH:7]2)([O-:3])=[O:2].[N+:1]([C:4]1[CH:12]=[CH:11][C:10]2[C:6](=[CH:7][N:8]([CH2:17][C:16]3[CH:19]=[CH:20][CH:21]=[C:14]([F:13])[CH:15]=3)[N:9]=2)[CH:5]=1)([O-:3])=[O:2]

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 215015-NitroindazoleHCID 680073-Fluorobenzyl bromide

Produkt 2

HCID 21049421HCID 21049421, VerbindungAusbeute 37 %HCID 219664901-(3-fluorobenzyl)-5-nitro-1H-indazoleAusbeute 32 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

5-nitroindazole (15 g, 92 mmol, 1 eq), 3-fluorobenzylbromide (14.7 mL, 119.5 mmol, 1.3 eq) and potassium carbonate 25.4 g (184 mmol, 2 equiv) were suspended in 150 mL acetonitrile. The reaction mixture was stirred at 70° C. for 12 h, and then allowed to cool to rt. The resultant solid was filtered and washed with CH2Cl2, and the filtrate concentrated in vacuo. The crude mixture of regioisomeric products was purified by column chromatography (5:1 to 4:1 Hex/EtOAc), yielding 5-nitro-1-N-(3-fluorobenzyl)indazole (7.9 g, 32%) and 5-nitro-2-N-(3-fluorobenzyl)indazole (9.2 g, 37%) as yellow solids.

Aufarbeitung

  1. temperatureto cool to rt
  2. filtrationThe resultant solid was filtered
  3. washwashed with CH2Cl2
  4. concentrationthe filtrate concentrated in vacuo
  5. additionThe crude mixture of regioisomeric products
  6. customwas purified by column chromatography (5:1 to 4:1 Hex/EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-ccedf090936f47639c8c200e442da7b6
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08207172B2

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