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Tetrahydrofuran → 3-(5-Bromo-pyridin-3-yl)-quinoline

HRID 383203
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 383203
Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Br:8])[CH:7]=1.CC1(C)C(C)(C)OB([C:17]2[CH:18]=[N:19][C:20]3[C:25]([CH:26]=2)=[CH:24][CH:23]=[CH:22][CH:21]=3)O1.C([O-])([O-])=O.[K+].[K+].C1COCC1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O.C1(C)C=CC=CC=1>[Br:8][C:6]1[CH:7]=[C:2]([C:17]2[CH:18]=[N:19][C:20]3[C:25]([CH:26]=2)=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH:3]=[N:4][CH:5]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 4

HCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 693693,5-DibromopyridineHCID 108485903-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)quinoline

Produkt 1

HCID 120122403-(5-Bromo-pyridin-3-yl)-quinolineAusbeute 98,4 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 74236
Tetrabutylammonium Bromide
Katalysator
HCID 178418397HCID 178418397, VerbindungKatalysator
HCID 962WaterLösungsmittel
HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

1.11 g (4.7 mmol) of 3,5-dibromo-pyridin, 1.0 g (3.92 mmol) of 3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-quinoline, 0.45 g of tetrakis(triphenylphosphine)palladium(0), 7.84 ml of 2 M K2CO3 and 1.26 g of tetrabutylammoniumbromide were added to a 100 ml round-bottom flask in an argon atmosphere, and 30 ml of THF and 15 ml of toluene were added thereto. Then, the mixture was refluxed at 100° C. for 16 hours. When the mixture solution turned dark brown, water was added thereto and the mixture was subject to extraction using chloroform. Then, an organic layer extracted therefrom was dried using anhydrous magnesium sulfate and filtered. A solvent was removed and the resultant was separated using a silica gel column chromatography to obtain 1.1 g of white solid 3-(5-bromo-pyridin-3-yl)-quinoline which was identified by an atmospheric pressure chemical ionization (APCI) using LCMS (SHIMADZU, LCMS-IT-TOF). As a result, a main peak was observed at [M+H]+=285.

Aufarbeitung

  1. additionwere added
  2. extractionthe mixture was subject to extraction
  3. extractionThen, an organic layer extracted
  4. customtherefrom was dried
  5. filtrationfiltered
  6. customA solvent was removed
  7. customthe resultant was separated

Quellen und Nachweise

ORD-Eintrag
ord-abc8b06cfe5c4a7aa2d98e0b2bc37d7c
Quelldatensatz
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08367220B2

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