HCID 66767215, Verbindung → HCID 66767283, Verbindung

HRID 1662009Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1662009
[F:1][C:2]1[CH:30]=[C:29]([N+:31]([O-])=O)[CH:28]=[CH:27][C:3]=1[O:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][C:13]=1[C:14]1[CH:15]=[N:16][N:17]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH:18]=1)[N:10]([CH3:26])[N:9]=[CH:8]2>[Pd].C1COCC1>[NH2:31][C:29]1[CH:28]=[CH:27][C:3]([O:4][C:5]2[CH:6]=[C:7]3[C:11](=[CH:12][C:13]=2[C:14]2[CH:15]=[N:16][N:17]([C:19]([O:21][C:22]([CH3:24])([CH3:25])[CH3:23])=[O:20])[CH:18]=2)[N:10]([CH3:26])[N:9]=[CH:8]3)=[C:2]([F:1])[CH:30]=1

Komponenten

4

Edukt 1

HCID 66767215HCID 66767215, Verbindung

Produkt 1

HCID 66767283HCID 66767283, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysator2×HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
35 °C

Versuchsvorschrift

To a 3 gallon tank is added tert-butyl 4-(5-(2-fluoro-4-nitrophenoxy)-1-methyl-1H-indazol-6-yl)-1H-pyrazole-1-carboxylate (433.0 g, 952.8 mmol) followed by THF (6.5 L) and Pd/C (21.65 g, 10% Pd/C and 21.65 g, 5% Pd/C). The mixture is heated to 35° C. under hydrogen gas for 2 hours. The reaction is then cooled to RT and allowed to stir under hydrogen gas overnight, then is heated to 40° C. under hydrogen gas for seven hours. An additional 2 g Pd/C (1 g, 10% Pd/C and 1 g, 5% Pd/C) is added and stirred under hydrogen gas for another hour and cooled to RT. The mixture is again stirred under hydrogen gas overnight and the reaction is completed. The mixture is filtered over a combination of GFF® and Watman® paper. The filtrate is concentrated to a slightly yellow solid (446 g, 110% recovery).

Aufarbeitung

  1. temperatureThe reaction is then cooled to RT
  2. temperatureis heated to 40° C. under hydrogen gas for seven hours
  3. stirringstirred under hydrogen gas for another hour
  4. temperaturecooled to RT
  5. stirringThe mixture is again stirred under hydrogen gas overnight
  6. filtrationThe mixture is filtered over a combination of GFF® and Watman® paper
  7. concentrationThe filtrate is concentrated to a slightly yellow solid (446 g, 110% recovery)

Quellen und Nachweise

ORD-Eintrag
ord-c1885dbb86ba41cdb871fc94f04cd52a
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08030302B2

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