Potassium Carbonate → Methyl 3-((dipropylamino)carbonyl]-5-ethylbenzoate

HRID 14002

Reaktionsgleichung

Reaktionsgleichung von HRID 14002
[CH2:1](B(O)O)[CH3:2].C(=O)([O-])[O-].[K+].[K+].[Cl-].[Li+].Br[C:15]1[CH:16]=[C:17]([CH:22]=[C:23]([C:25]([N:27]([CH2:31][CH2:32][CH3:33])[CH2:28][CH2:29][CH3:30])=[O:26])[CH:24]=1)[C:18]([O:20][CH3:21])=[O:19]>CN(C=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:28]([N:27]([CH2:31][CH2:32][CH3:33])[C:25]([C:23]1[CH:22]=[C:17]([CH:16]=[C:15]([CH2:1][CH3:2])[CH:24]=1)[C:18]([O:20][CH3:21])=[O:19])=[O:26])[CH2:29][CH3:30]

Komponenten

7

Edukt 4

HCID 11430Potassium CarbonateHCID 433294Lithium ChlorideHCID 521157Ethylboronic acidHCID 21939662Methyl 3-bromo-5-(dipropylcarbamoyl)benzoate

Produkt 1

HCID 22593628Methyl 3-((dipropylamino)carbonyl]-5-ethylbenzoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

Ethylboronic acid (0.800 g, 10.8 mmol), dichlorobis(triphenylphosphine)-palladium(II) (0.252 g, 0.360 mmol), potassium carbonate (2.50 g, 18.0 mmol) and lithium chloride (0.151 g, 3.60 mmol) are added to a mixture of methyl 3-bromo-5-[(dipropylamino)carbonyl]benzoate (1.23 g, 3.60 mmol) in dry DMF (20 mL). The mixture is heated at 100 degrees C. for 18 hours. The mixture is then partitioned between ethyl acetate and water. The phases are separated and the ethyl acetate phase is washed with saline, dried over sodium sulfate and concentrated. The concentrate is column chromatographed (silica gel; ethyl acetate/hexanes, 15/85) to give the title compound, MS (ESI+) for C17H25NO3 m/z (M+H)+=292.2.

Aufarbeitung

  1. customThe mixture is then partitioned between ethyl acetate and water
  2. customThe phases are separated
  3. washthe ethyl acetate phase is washed with saline
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customchromatographed (silica gel; ethyl acetate/hexanes, 15/85)

Quellen und Nachweise

ORD-Eintrag
ord-87b264a8e2c347b0ba0c3634ea5dddab
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07727997B2

Verknüpfte Notizen

Wird geladen…