Citric Acid → HCID 66990697, Verbindung

HRID 454771Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 454771
C(=O)([O-])[O-].[Na+].[Na+].B1([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([O:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH:17]=2)OC(C)(C)C(C)(C)O1.Br[C:31]1[CH:43]=[CH:42][C:34]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])=[C:33]([NH:44][C:45]([C:47]2[CH:48]=[N:49][CH:50]=[C:51]([C:53]3[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=3)[CH:52]=2)=[O:46])[CH:32]=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>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.COCCOC.O>[C:26]([O:25][C:23]([O:22][C:18]1[CH:17]=[C:16]([C:31]2[CH:43]=[CH:42][C:34]([C:35]([O:37][C:38]([CH3:40])([CH3:39])[CH3:41])=[O:36])=[C:33]([NH:44][C:45]([C:47]3[CH:48]=[N:49][CH:50]=[C:51]([C:53]4[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=4)[CH:52]=3)=[O:46])[CH:32]=2)[CH:21]=[CH:20][CH:19]=1)=[O:24])([CH3:27])([CH3:28])[CH3:29]

Komponenten

9

Edukt 4

HCID 311Citric AcidHCID 10340Sodium CarbonateHCID 27739553-(tert-Butoxycarbonyloxy)phenylboronic acid pinacol esterHCID 58508430Tert-butyl 4-bromo-2-(5-phenylpyridine-3-carboxamido)benzoate

Produkt 1

HCID 66990697HCID 66990697, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 4

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

Versuchsvorschrift

Water (0.6 mL), sodium carbonate (58 mg), tert-butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenylcarbonate (85 mg), and bis(triphenylphosphine)palladium(II) dichloride (3.0 mg) were added to an ethylene glycol dimethyl ether (2.0 mL) suspension of tert-butyl 4-bromo-2-(5-phenylpyridine-3-carboxamido)benzoate (0.10 g), followed by heating to reflux under a nitrogen atmosphere for 1 hour. The reaction mixture was cooled to room temperature, and then ethyl acetate and a 10% aqueous solution of citric acid 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 tert-butyl 4-(3-(tert-butoxycarbonyl)oxyphenyl)-2-(5-phenylpyridine-3-carboxamido)benzoate.

Aufarbeitung

  1. temperatureby heating
  2. temperatureto reflux under a nitrogen atmosphere for 1 hour
  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-f1d1e6e4d93643968635cd94ef417b05
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08492582B2

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