Potassium Acetate → Ethyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-{2-[4-(trifluoromethoxy)phenoxy]ethyl}-1H-indole-2-carboxylate

HRID 513203Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 513203
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][CH2:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][C:21]([F:24])([F:23])[F:22])=[CH:16][CH:15]=1)[C:6]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:5]2.[BH3:30].[OH:31][C:32]([C:35]([OH:38])([CH3:37])[CH3:36])([CH3:34])[CH3:33].CC([O-])=O.[K+]>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:33][C:32]1([CH3:34])[C:35]([CH3:37])([CH3:36])[O:38][B:30]([C:2]2[CH:3]=[C:4]3[C:8](=[CH:9][CH:10]=2)[N:7]([CH2:11][CH2:12][O:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][C:21]([F:24])([F:23])[F:22])=[CH:16][CH:15]=2)[C:6]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:5]3)[O:31]1

Komponenten

6

Edukt 3

HCID 517044Potassium AcetateHCID 71212593Ethyl 5-bromo-1-{2-[4-(trifluoromethoxy)phenoxy]ethyl}-1H-indole-2-carboxylateHCID 178419189HCID 178419189, Verbindung

Produkt 1

HCID 71212616Ethyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-{2-[4-(trifluoromethoxy)phenoxy]ethyl}-1H-indole-2-carboxylateAusbeute 76,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

The ethyl 5-bromo-1-{2-[4-(trifluoromethoxy)phenoxy]ethyl}-1H-indole-2-carboxylate (812 mg, 1.7 mmol), pinacol borane (873 mg, 3.4 mmol), X Phos (98 mg, 0.21 mmol) and KOAc (540 mg, 5.5 mmol) were combined in 8 mL of Dioxane. The mixture was degassed under vacuum and backfilled with N2. Palladium acetate (23 mg, 0.1 mmol) was added, and the mixture was degassed and back filled again. The mixture was left to stir overnight at 85° C. EtOAc was added and the mixture was filtered through a pad of celite, concentrated in vacuo, and purified on silica (0-30% EtOAc in hexanes) to give the title product (675 mg).

Aufarbeitung

  1. customThe mixture was degassed under vacuum
  2. customthe mixture was degassed
  3. additionback filled again
  4. waitThe mixture was left
  5. additionEtOAc was added
  6. filtrationthe mixture was filtered through a pad of celite
  7. concentrationconcentrated in vacuo
  8. custompurified on silica (0-30% EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-bbd470b1e6e84acd91a0a14a986e1657
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09102673B2

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