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Sodium Carbonate → HCID 66990340, Verbindung

HRID 454670
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 454670
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+].[CH2:17]([O:24][C:25]1[CH:47]=[CH:46][C:45]([N:48]2[CH2:53][CH2:52][CH2:51][CH2:50][CH2:49]2)=[CH:44][C:26]=1[C:27]([NH:29][C:30]1[CH:42]=[C:41](Br)[CH:40]=[CH:39][C:31]=1[C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])=[O:28])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>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.C(OCC)(=O)C.O.COCCOC>[CH2:17]([O:24][C:25]1[CH:47]=[CH:46][C:45]([N:48]2[CH2:53][CH2:52][CH2:51][CH2:50][CH2:49]2)=[CH:44][C:26]=1[C:27]([NH:29][C:30]1[CH:42]=[C:41]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[CH3:1])[CH:40]=[CH:39][C:31]=1[C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])=[O:28])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 3

HCID 10340Sodium CarbonateHCID 27332672-Methylphenyl boronic acidHCID 66990213HCID 66990213, Verbindung

Produkt 1

HCID 66990340HCID 66990340, VerbindungAusbeute 98,1 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 178418476HCID 178418476, VerbindungKatalysator
HCID 962WaterLösungsmittel2×
HCID 80711,2-DimethoxyethaneLösungsmittel
HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Water (0.60 mL), 2-methylphenylboronic acid (0.029 g), sodium carbonate (0.047 g), and bis(triphenylphosphine)palladium(II) dichloride (2.5 mg) were added to an ethylene glycol dimethyl ether (2.0 mL) solution of tert-butyl 2-(2-(benzyloxy)-5-(piperidin-1-yl)benzamido)-4-bromobenzoate (0.10 g), followed by heating to reflux under a nitrogen atmosphere for 2 hours. The reaction mixture was cooled to room temperature, and water and ethyl acetate were added thereto. The organic layer was separated, washed with a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography [eluent: 99-91% hexane/ethyl acetate] to obtain 0.10 g of tert-butyl 2-(2-(benzyloxy)-5-(piperidin-1-yl)benzamido)-4-(2-methylphenyl)benzoate.

Aufarbeitung

  1. temperatureby heating
  2. temperatureto reflux under a nitrogen atmosphere for 2 hours
  3. customThe organic layer was separated
  4. washwashed with a saturated aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography [eluent: 99-91% hexane/ethyl acetate]

Quellen und Nachweise

ORD-Eintrag
ord-ba5201f78b1c4608ad22e313f3db7548
Quelldatensatz
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08492582B2

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