Potassium Carbonate → HCID 71468849, Verbindung

HRID 1401088Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1401088
[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]([N:14]([CH:24]([CH3:26])[CH3:25])[NH:15][C:16](=[O:23])[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:13])=[CH:2]1.C([O-])([O-])=O.[K+].[K+].[C:33](Cl)([C:35]([CH3:38])([CH3:37])[CH3:36])=[O:34]>CN(C1C=CN=CC=1)C.CN(C=O)C.CCOC(C)=O>[CH:24]([N:14]([C:12](=[O:13])/[CH:11]=[CH:10]/[C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[N:1]([C:33](=[O:34])[C:35]([CH3:38])([CH3:37])[CH3:36])[CH:2]=1)[NH:15][C:16](=[O:23])[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)([CH3:26])[CH3:25]

Komponenten

7

Edukt 3

HCID 11430Potassium CarbonateHCID 62493Pivaloyl chlorideHCID 71468594HCID 71468594, Verbindung

Produkt 1

HCID 71468849HCID 71468849, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a round bottom flask, (E)-N′-(3-(1H-indol-3-yl)acryloyl)-N′-isopropylbenzohydrazide (60 mg, 0.17 mmol, 1.0 equivalent), K2CO3 (71.6 mg, 0.51 mmol, 3.0 equivalent), and DMAP (cat, 0.12 equivalent) were introduced and dissolved in DMF, after which Piv-Cl (0.04 ml, 0.34 mmol, 2.0 equivalent) was introduced. After stirring at room temperature for 24 hr, the reaction mixture was diluted with EtOAc, washed with water and brine, dried with anhydrous MgSO4, filtered, and concentrated under reduced pressure. The residue was separated through silica gel chromatography (n-hexane:EtOAc:methanol=7:3:1) and dried so that solid form of (E)-N′-(3-(1-acetyl-1H-indol-3-yl)acryloyl)-N′-isopropylbenzohydrazide was obtained. (10.3 mg, 14%).

Aufarbeitung

  1. washwashed with water and brine
  2. dry with materialdried with anhydrous MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was separated through silica gel chromatography (n-hexane:EtOAc:methanol=7:3:1)
  6. dry with materialdried so that solid form of (E)-N′-(3-(1-acetyl-1H-indol-3-yl)acryloyl)-N′-isopropylbenzohydrazide
  7. customwas obtained

Quellen und Nachweise

ORD-Eintrag
ord-40158dcc28dc408c8a8f31486a688ec9
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08906952B2

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