Cesium fluoride → 2',6'-Bis(2,2,6,6-tetramethylpiperidin-1-yl)-2,3'-bipyridine

HRID 1779137Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1779137
Br[C:2]1[C:3]([N:18]2[C:23]([CH3:25])([CH3:24])[CH2:22][CH2:21][CH2:20][C:19]2([CH3:27])[CH3:26])=[N:4][C:5]([N:8]2[C:13]([CH3:15])([CH3:14])[CH2:12][CH2:11][CH2:10][C:9]2([CH3:17])[CH3:16])=[CH:6][CH:7]=1.C([Sn](CCCC)(CCCC)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][N:34]=1)CCC.[F-].[Cs+]>C1(C)C=CC=CC=1.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>[CH3:27][C:19]1([CH3:26])[CH2:20][CH2:21][CH2:22][C:23]([CH3:25])([CH3:24])[N:18]1[C:3]1[C:2]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][N:34]=2)=[CH:7][CH:6]=[C:5]([N:8]2[C:9]([CH3:16])([CH3:17])[CH2:10][CH2:11][CH2:12][C:13]2([CH3:15])[CH3:14])[N:4]=1

Komponenten

6

Edukt 3

HCID 25953Cesium fluorideHCID 6077842-(Tributylstannyl)pyridineHCID 676092893-Bromo-2,6-bis(2,2,6,6-tetramethylpiperidin-1-yl)pyridine

Produkt 1

HCID 678921422',6'-Bis(2,2,6,6-tetramethylpiperidin-1-yl)-2,3'-bipyridine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixture of 3-Bromo-2,6-bis(2,2,6,6-tetramethylpiperidin-1-yl)pyridine (0.4 g, 0.92 mmol), 2-(tributylstannyl)pyridine (0.4 g, 1.10 mmol), Pd(PPh3)4 (0.053 g, 0.046 mmol), and Cesium fluoride (0.28 g, 1.83 mmol) in Toluene (30 ml) was stirred under reflux for 2 days. After cooling down to room temperature the reaction was quenched with saturated CsF aqueous solution (100 mL). The product was extracted with ethylacetate. The product was purified by column chromatography on silica gel and obtained as white solide (Rf=0.5 in Ethylacetate:hexane=1:4, Yield=50 mg (12.5%))

Aufarbeitung

  1. temperatureunder reflux for 2 days
  2. customwas quenched with saturated CsF aqueous solution (100 mL)
  3. extractionThe product was extracted with ethylacetate
  4. customThe product was purified by column chromatography on silica gel
  5. customobtained as white solide (Rf=0.5 in Ethylacetate:hexane=1:4, Yield=50 mg (12.5%))

Quellen und Nachweise

ORD-Eintrag
ord-f26caf7e0acf4eb181c046c258d077f3
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09269912B2

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