Cesium carbonate → 1-(4-Fluorophenyl)-6-chloro-5-methoxy-1H-indazole

HRID 1098881

Reaktionsgleichung

Reaktionsgleichung von HRID 1098881
[Cl:1][C:2]1[C:9]([O:10][CH3:11])=[CH:8][C:5]([CH:6]=O)=[C:4](F)[CH:3]=1.[F:13][C:14]1[CH:19]=[CH:18][C:17]([NH:20][NH2:21])=[CH:16][CH:15]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN1CCCC1>[F:13][C:14]1[CH:19]=[CH:18][C:17]([N:20]2[C:4]3[C:5](=[CH:8][C:9]([O:10][CH3:11])=[C:2]([Cl:1])[CH:3]=3)[CH:6]=[N:21]2)=[CH:16][CH:15]=1

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 69982(4-Fluorophenyl)hydrazineHCID 149282684-Chloro-2-fluoro-5-methoxybenzaldehyde

Produkt 1

HCID 593398871-(4-Fluorophenyl)-6-chloro-5-methoxy-1H-indazole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 84541-MethylpyrrolidineLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

4-Chloro-2-fluoro-5-methoxy benzaldehyde (204 mg, 1.1 mmol) and 4-fluorophenylhydrazine (176 mg, 1.1 mmol) were dissolved in N-methylpyrrolidine (5 mL). After addition of cesium carbonate (1.15 g, 3.3 mmol) the mixture was heated in a microwave reactor (CEM Discovery, 150 Watt) to 150° C. for 20 min. After dilution with DCM the mixture was washed with sat. NaHCO3, brine and the organic phase was evaporated. After purification of the crude by flash chromatography on silica gel 253 mg (84%) of the subtitle compound were obtained.

Aufarbeitung

  1. washAfter dilution with DCM the mixture was washed with sat. NaHCO3, brine
  2. customthe organic phase was evaporated
  3. customAfter purification of the crude by flash chromatography on silica gel 253 mg (84%) of the subtitle compound
  4. customwere obtained

Quellen und Nachweise

ORD-Eintrag
ord-8a23e4dc89754506960f2ee71ed06f7d
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08143290B2

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