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Sodium Carbonate → Tert-butyl 4-(isoquinolin-4-yl)-2-nitrobenzoate

HRID 454512
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 454512
C(=O)([O-])[O-].[Na+].[Na+].CC1(C)C(C)(C)OB([C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:18]=[N:17][CH:16]=2)O1.Br[C:27]1[CH:39]=[CH:38][C:30]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])=[C:29]([N+:40]([O-:42])=[O:41])[CH:28]=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.O.C(OCC)(=O)C.COCCOC>[CH:18]1[C:19]2[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:15]([C:27]2[CH:39]=[CH:38][C:30]([C:31]([O:33][C:34]([CH3:36])([CH3:37])[CH3:35])=[O:32])=[C:29]([N+:40]([O-:42])=[O:41])[CH:28]=2)=[CH:16][N:17]=1
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Komponenten

8

Edukt 3

HCID 10340Sodium CarbonateHCID 27605944-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)isoquinolineHCID 26369829tert-Butyl 4-bromo-2-nitrobenzoate

Produkt 1

HCID 58508799Tert-butyl 4-(isoquinolin-4-yl)-2-nitrobenzoateAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 4

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

Versuchsvorschrift

Water (15 mL), sodium carbonate (4.6 g), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoquinoline (5.1 g), and bis(triphenylphosphine)palladium(II) dichloride (0.24 g) were added to an ethylene glycol dimethyl ether (50 mL) solution of tert-butyl 4-bromo-2-nitrobenzoate (5.0 g), followed by heating to reflux under a nitrogen atmosphere for 2 hours. The reaction mixture was cooled to room temperature, and then ethyl acetate and water 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: 85-75% hexane/ethyl acetate] to obtain 5.8 g of tert-butyl 4-(isoquinolin-4-yl)-2-nitrobenzoate as a brown oily substance.

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: 85-75% hexane/ethyl acetate]

Quellen und Nachweise

ORD-Eintrag
ord-c5f00effe90b46de926f3c225148c73c
Quelldatensatz
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08492582B2

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