Hydrochloric Acid → HCID 86713217, Verbindung

HRID 1056819

Reaktionsgleichung

Reaktionsgleichung von HRID 1056819
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH:10]=[CH:11][C:12](=[O:17])[CH2:13][C:14](=[O:16])[CH3:15])=[CH:2]1.[B]=O.[N:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[CH2:26][O:27][C:28]1[CH:35]=[CH:34][C:31]([CH:32]=O)=[CH:30][CH:29]=1.B(OC(C)C)(OC(C)C)OC(C)C.N1CCCCC1.Cl.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C.[Cl-].[Na+].O>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](/[CH:10]=[CH:11]/[C:12](=[O:17])[CH2:13][C:14](=[O:16])/[CH:15]=[CH:32]/[C:31]2[CH:30]=[CH:29][C:28]([O:27][CH2:26][C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][N:20]=3)=[CH:35][CH:34]=2)=[CH:2]1

Komponenten

10

Edukt 7

HCID 313Hydrochloric AcidHCID 8082PiperidineHCID 21531Triisopropyl borateHCID 516892Sodium BicarbonateHCID 7596674-(Pyridin-2-ylmethoxy)benzaldehydeHCID 6327189Boron monoxideHCID 86713218HCID 86713218, Verbindung

Produkt 1

HCID 86713217HCID 86713217, VerbindungAusbeute 45 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8857Ethyl AcetateLösungsmittel2×HCID 57417360Sodium chloride; waterLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

In a 20 mL reaction vessel were placed 31.0 mg (136 μmol) of 6-(1H-indol-3-yl)hex-5-ene-2,4-dione and 13.2 mg (0.190 mmol) of boron oxide and they were dissolved in 0.88 mL of ethyl acetate. To the mixture under stirring at 70° C., 29 mg (0.14 mmol) of 4-(2-pyridylmethoxy)benzaldehyde and 62 μL (0.27 mmol) of triisopropyl borate were sequentially added. After the mixture was stirred at the same temperature for 1 hour, a solution of 2.7 μL (27 μmol) of piperidine in ethyl acetate (0.135 mL) was added and the mixture was further stirred for 1 hour. To the reaction mixture was added a 1:1 solution (0.4 mL) of 1 N hydrochloric acid and saturated brine at room temperature and the mixture was stirred for 5 minutes to 1 hour (further, the mixture was neutralized with a saturated sodium bicarbonate aqueous solution as needed). The resulting organic phase was directly subjected to purification by silica gel column chromatography (hexane/ethyl acetate or methylene chloride/methanol) to give 25.7 mg (45% yield) of the title compound as an orange powder.

Aufarbeitung

  1. customIn a 20 mL reaction vessel
  2. stirringAfter the mixture was stirred at the same temperature for 1 hour
  3. stirringthe mixture was further stirred for 1 hour
  4. stirringthe mixture was stirred for 5 minutes to 1 hour (further, the mixture
  5. customThe resulting organic phase was directly subjected to purification by silica gel column chromatography (hexane/ethyl acetate or methylene chloride/methanol)

Quellen und Nachweise

ORD-Eintrag
ord-92ca296526514b4f828e0c350bd1f3a9
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09399635B2

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