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

HRID 13171

Reaktionsgleichung

Reaktionsgleichung von HRID 13171
F[CH2:2][O:3][C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1C=O.Cl.[F:13][C:14]1[CH:19]=[CH:18][C:17]([NH:20][NH2:21])=[CH:16][CH:15]=1.[C:22](=O)([O-])[O-].[Cs+].[Cs+]>CN1C(=O)CCC1.ClCCl>[F:13][C:14]1[CH:19]=[CH:18][C:17]([N:20]2[C:9]3[C:10](=[CH:11][C:4]([O:3][CH3:2])=[CH:5][CH:8]=3)[CH:22]=[N:21]2)=[CH:16][CH:15]=1

Komponenten

6

Edukt 3

HCID 10796Cesium carbonateHCID 699814-Fluorophenylhydrazine hydrochlorideHCID 200615072-(Fluoromethoxy)benzaldehyde

Produkt 1

HCID 593396221-(4-Fluorophenyl)-5-methoxy-1H-indazole

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

A mixture of 2-fluoromethoxybenzaldehyde (2.1 mmol, 320 mg), 4-fluorophenylhydrazine hydrochloride (2.1 mmol, 340 mg) and cesium carbonate (3 mmol, 2.0 g) in NMP (6 ml) was heated in a microwave reactor (300 W, 20 min, 150° C.). After cooling to r.t. the reaction mixture was diluted with dichloromethane (20 ml) and washed with 1M HCl, and sat. NaHCO3. The organic layer was dried over Na2SO4, concentrated, and purified by flash chromatography on silica gel (heptane-ethyl acetate).

Aufarbeitung

  1. temperatureAfter cooling to r.t. the reaction mixture
  2. washwashed with 1M HCl, and sat. NaHCO3
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated
  5. custompurified by flash chromatography on silica gel (heptane-ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-c8e87cd6e7c044e2b1f536b44b2227db
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07728030B2

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