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Sodium Carbonate → Tert-butyl 4-(3-(diethylamino)phenyl)-2-(5-phenylpyridine-3-carboxamido)benzoate

HRID 454770
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 454770
Br[C:2]1[CH:14]=[CH:13][C:5]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])=[C:4]([NH:15][C:16]([C:18]2[CH:19]=[N:20][CH:21]=[C:22]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH:23]=2)=[O:17])[CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[CH2:36]([N:38]([CH2:54][CH3:55])[C:39]1[CH:44]=[CH:43][CH:42]=[C:41](B2OC(C)(C)C(C)(C)O2)[CH:40]=1)[CH3:37]>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(Cl)(Cl)Cl.O.COCCOC>[CH2:54]([N:38]([CH2:36][CH3:37])[C:39]1[CH:40]=[C:41]([C:2]2[CH:14]=[CH:13][C:5]([C:6]([O:8][C:9]([CH3:11])([CH3:10])[CH3:12])=[O:7])=[C:4]([NH:15][C:16]([C:18]3[CH:19]=[N:20][CH:21]=[C:22]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[CH:23]=3)=[O:17])[CH:3]=2)[CH:42]=[CH:43][CH:44]=1)[CH3:55]
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Komponenten

8

Edukt 3

HCID 10340Sodium CarbonateHCID 58508430Tert-butyl 4-bromo-2-(5-phenylpyridine-3-carboxamido)benzoateHCID 66990273N,N-diethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

Produkt 1

HCID 66990777Tert-butyl 4-(3-(diethylamino)phenyl)-2-(5-phenylpyridine-3-carboxamido)benzoateAusbeute 94,8 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 178418476
HCID 178418476, Verbindung
Katalysator
HCID 962WaterLösungsmittel2×
HCID 6212ChloroformLösungsmittel
HCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

Tert-butyl 4-bromo-2-(5-phenylpyridine-3-carboxamido)benzoate (0.11 g), sodium carbonate (64 mg), water (0.30 mL), and bis(triphenylphosphine)palladium(II) dichloride (3.5 mg) were added to an ethylene glycol dimethyl ether (1.0 mL) solution of N,N-diethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (83 mg), followed by heating to reflux under a nitrogen atmosphere for 2 hours and 40 minutes. The reaction mixture was cooled to room temperature, and then water and chloroform were added thereto. The organic layer was separated 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: 90-70% hexane/ethyl acetate] to obtain 0.12 g of tert-butyl 4-(3-(diethylamino)phenyl)-2-(5-phenylpyridine-3-carboxamido)benzoate as a yellow solid.

Aufarbeitung

  1. temperatureby heating
  2. temperatureto reflux under a nitrogen atmosphere for 2 hours and 40 minutes
  3. customThe organic layer was separated
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography [eluent: 90-70% hexane/ethyl acetate]

Quellen und Nachweise

ORD-Eintrag
ord-27ae272f2e64466a8460117e0ce86feb
Quelldatensatz
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08492582B2

Notizen zur Reaktion

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