Toluene → N-{2-[4-(6-chloro-3-formyl-1H-indol-5-yl)phenoxy]ethyl}acetamide

HRID 338245

Reaktionsgleichung

Reaktionsgleichung von HRID 338245
CC1(C)COB([C:8]2[CH:20]=[CH:19][C:11]([O:12][CH2:13][CH2:14][NH:15][C:16](=[O:18])[CH3:17])=[CH:10][CH:9]=2)OC1.Br[C:23]1[CH:24]=[C:25]2[C:29](=[CH:30][C:31]=1[Cl:32])[NH:28][CH:27]=[C:26]2[CH:33]=[O:34].C(=O)([O-])[O-].[K+].[K+].C1(C)C=CC=CC=1>C(O)C.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].C(OCC)(=O)C>[Cl:32][C:31]1[CH:30]=[C:29]2[C:25]([C:26]([CH:33]=[O:34])=[CH:27][NH:28]2)=[CH:24][C:23]=1[C:8]1[CH:9]=[CH:10][C:11]([O:12][CH2:13][CH2:14][NH:15][C:16](=[O:18])[CH3:17])=[CH:19][CH:20]=1

Komponenten

8

Edukt 4

HCID 1140TolueneHCID 11430Potassium CarbonateHCID 866985665-bromo-6-chloro-1H-indole-3-carbaldehydeHCID 86698589N-(2-(4-(5,5-Dimethyl-1,3,2-dioxaborinan-2-yl)phenoxy)ethyl)acetamide

Produkt 1

HCID 86698590N-{2-[4-(6-chloro-3-formyl-1H-indol-5-yl)phenoxy]ethyl}acetamideAusbeute 65 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 702EthanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

To a solution of N-{2-[4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)phenoxy]ethyl}acetamide (100 mg, 0.35 mmol) in ethanol (1.4 mL) were added 5-bromo-6-chloro-1H-indole-3-carbaldehyde (107 mg, 0.42 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (26 mg, 0.036 mmol), 2M aqueous potassium carbonate (2 mol/L, 0.7 mL) and toluene (4.2 mL). The mixture was degassed with nitrogen for 3 min and heated to 110° C. by microwave irradiation for 1 h. The mixture was concentrated in vacuo to give a residue, which was dissolved with ethyl acetate (50 mL) and washed with brine (2×15 mL). The organic layer was dried over sodium sulfate and concentrated in vacuo to give a brown residue, which was purified by flash chromatography (petroleum ether/ethyl acetate=10:1 to 2:1) to give N-{2-[4-(6-chloro-3-formyl-1H-indol-5-yl)phenoxy]ethyl}acetamide (80 mg, 65%) as a yellow solid.

Aufarbeitung

  1. customThe mixture was degassed with nitrogen for 3 min
  2. concentrationThe mixture was concentrated in vacuo
  3. customto give a residue, which
  4. washwashed with brine (2×15 mL)
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customto give a brown residue, which
  8. customwas purified by flash chromatography (petroleum ether/ethyl acetate=10:1 to 2:1)

Quellen und Nachweise

ORD-Eintrag
ord-3185bdd7344d49bc85752917c8440109
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08889730B2

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