HCID 86685698, Verbindung → HCID 86685700, Verbindung

HRID 536577Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 536577
C[O:2][C:3](=[O:27])[CH2:4][CH2:5][C:6]1[CH:10]=[C:9]([CH3:11])[N:8]([CH2:12][C:13]2[CH:18]=[C:17](Br)[CH:16]=[CH:15][C:14]=2[O:20][CH2:21][CH:22]([CH2:25][CH3:26])[CH2:23][CH3:24])[N:7]=1.[Zn](C)[CH3:29]>O1CCOCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH2:23]([CH:22]([CH2:25][CH3:26])[CH2:21][O:20][C:14]1[CH:15]=[CH:16][C:17]([CH3:29])=[CH:18][C:13]=1[CH2:12][N:8]1[C:9]([CH3:11])=[CH:10][C:6]([CH2:5][CH2:4][C:3]([OH:2])=[O:27])=[N:7]1)[CH3:24]

Komponenten

5

Edukt 2

HCID 86685698HCID 86685698, VerbindungHCID 178477796HCID 178477796, Verbindung

Produkt 1

HCID 86685700HCID 86685700, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
105 °C

Versuchsvorschrift

A mixture of 3-{1-[5-Bromo-2-(2-ethyl-butoxy)-benzyl]-5-methyl-1H-pyrazol-3-yl}-propionic acid methyl ester (0.1363 g, 0.31 mmol), Pd(dppf)Cl2 (0.00506 g, 0.00621 mmol), Zn(CH3)2 (0.31 mlg, 0.62 mmol in 1,4-dioxane (0.93 ml) heated at 105° C. under a N2 atmosphere for 1 h 50 min. The mixture was cooled to RT, quenched with MeOH (0.2 ml) and partitioned between 1M HCl and EtOAc. The organic layer was washed with brine, dried (MgSO4) and evaporated to dryness. The residue was converted to the title compound following the method in Example 1, Step 8.

Aufarbeitung

  1. temperatureThe mixture was cooled to RT
  2. customquenched with MeOH (0.2 ml)
  3. custompartitioned between 1M HCl and EtOAc
  4. washThe organic layer was washed with brine
  5. dry with materialdried (MgSO4)
  6. customevaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-3d6bd2a1003946918a3205e28cafae67
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08859606B2

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