Sodium Carbonate → Tert-butyl 2-(2-(benzyloxy)-5-(furan-3-yl)benzamido)-4-phenylbenzoate

HRID 454584

Reaktionsgleichung

Reaktionsgleichung von HRID 454584
CC1(C)C(C)(C)OB([C:9]2[CH:13]=[CH:12][O:11][CH:10]=2)O1.C(=O)([O-])[O-].[Na+].[Na+].[CH2:21]([O:28][C:29]1[CH:56]=[CH:55][C:54](Br)=[CH:53][C:30]=1[C:31]([NH:33][C:34]1[CH:46]=[C:45]([C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)[CH:44]=[CH:43][C:35]=1[C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])=[O:32])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=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>[CH2:21]([O:28][C:29]1[CH:56]=[CH:55][C:54]([C:9]2[CH:13]=[CH:12][O:11][CH:10]=2)=[CH:53][C:30]=1[C:31]([NH:33][C:34]1[CH:46]=[C:45]([C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)[CH:44]=[CH:43][C:35]=1[C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])=[O:32])[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Komponenten

8

Edukt 3

HCID 10340Sodium CarbonateHCID 27739962-(Furan-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 66990333Tert-butyl 2-(2-(benzyloxy)-5-bromobenzamido)-4-phenylbenzoate

Produkt 1

HCID 66990487Tert-butyl 2-(2-(benzyloxy)-5-(furan-3-yl)benzamido)-4-phenylbenzoateAusbeute 84,3 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 962WaterLösungsmittel2×HCID 80711,2-DimethoxyethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Water (0.5 mL), 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)furan (0.070 g), sodium carbonate (0.076 g), and bis(triphenylphosphine)palladium(II) dichloride (4.2 mg) were added to an ethylene glycol dimethyl ether (1.7 mL) solution of tert-butyl 2-(2-(benzyloxy)-5-bromobenzamido)-4-phenylbenzoate (0.17 g), followed by heating to reflux under a nitrogen atmosphere for 1 hour and 40 minutes. 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: 95-80% hexane/ethyl acetate] to obtain 0.14 g of tert-butyl 2-(2-(benzyloxy)-5-(furan-3-yl)benzamido)-4-phenylbenzoate as a white solid.

Aufarbeitung

  1. temperatureby heating
  2. temperatureto reflux under a nitrogen atmosphere for 1 hour and 40 minutes
  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: 95-80% hexane/ethyl acetate]

Quellen und Nachweise

ORD-Eintrag
ord-8e2250212a5c4c7198b26d7ff2d890e6
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08492582B2

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