Potassium Carbonate → 3-[4-(6-chloro-3-formyl-1H-indol-5-yl)phenoxy]propanoic acid

HRID 1054784

Reaktionsgleichung

Reaktionsgleichung von HRID 1054784
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][NH:8]2)=[CH:4][C:3]=1B1OCC(C)(C)CO1.[C:19](=O)([O-])[O-:20].[K+].[K+].Br[C:26]1[CH:37]=[CH:36][C:29]([O:30][CH2:31][CH2:32][C:33]([OH:35])=[O:34])=[CH:28][CH:27]=1>O1CCOCC1.CN(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]>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH:19]=[O:20])=[CH:7][NH:8]2)=[CH:4][C:3]=1[C:26]1[CH:37]=[CH:36][C:29]([O:30][CH2:31][CH2:32][C:33]([OH:35])=[O:34])=[CH:28][CH:27]=1

Komponenten

7

Edukt 3

HCID 11430Potassium CarbonateHCID 74720343-(4-Bromophenoxy)propanoic acidHCID 866987336-chloro-5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-1H-indole

Produkt 1

HCID 866987723-[4-(6-chloro-3-formyl-1H-indol-5-yl)phenoxy]propanoic acidAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 6228DimethylformamideLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a solution of 6-chloro-5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-1H-indole (150 mg, 0.57 mmol) in dioxane (5 mL) and DMF (1 mL) was added N,N-dimethylformiminium chloride (155 mg, 1.21 mmol). The reaction mixture was stirred at room temperature for 20 min. 2 N potassium carbonate (314 mg, 2.28 mmol), 3-(4-bromophenoxy)propanoic acid (139 mg, 0.57 mmol) and Pd(dppf)Cl2 (21 mg, 0.028 mmol) were then added. The reaction was degassed with N2 and heated to 90° C. for 30 min. The reaction was extracted with ethyl acetate (10 mL×2). The organic layers were washed with brine (10 mL), dried over sodium sulfate, and concentrated to give the title compound (170 mg, 87% yield) as a brown oil.

Aufarbeitung

  1. customThe reaction was degassed with N2
  2. temperatureheated to 90° C. for 30 min
  3. extractionThe reaction was extracted with ethyl acetate (10 mL×2)
  4. washThe organic layers were washed with brine (10 mL)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-8463d63c20914b44893ec01cffa9c0b9
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09394285B2

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