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Water → 3-(4-(Tert-butyldimethylsilyloxy)cyclohex-1-enyl)-2-fluoropyridine

HRID 410234
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 410234
FC(F)(F)S(O[C:7]1[CH2:12][CH2:11][CH:10]([O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])[CH2:9][CH:8]=1)(=O)=O.C(=O)([O-])[O-].[Na+].[Na+].O.[F:30][C:31]1[C:36](B(O)O)=[CH:35][CH:34]=[CH:33][N:32]=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>[Si:14]([O:13][CH:10]1[CH2:11][CH2:12][C:7]([C:36]2[C:31]([F:30])=[N:32][CH:33]=[CH:34][CH:35]=2)=[CH:8][CH2:9]1)([C:17]([CH3:18])([CH3:19])[CH3:20])([CH3:15])[CH3:16]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 27832702-Fluoropyridine-3-boronic acidHCID 534150124-((tert-Butyldimethylsilyl)oxy)cyclohex-1-en-1-yl trifluoromethanesulfonate

Produkt 1

HCID 593268503-(4-(Tert-butyldimethylsilyloxy)cyclohex-1-enyl)-2-fluoropyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 178418397
HCID 178418397, Verbindung
Katalysator

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a sealable vessel was added 4-(tert-butyldimethylsilyloxy)cyclohex-1-enyl trifluoromethanesulfonate (1.90 g, 5.27 mmol), sodium carbonate as a 2N solution in water (7.91 mL, 15.81 mmol), and 2-fluoropyridin-3-ylboronic acid (0.891 g, 6.33 mmol) before adding tetrakis(triphenylphosphine)palladium(0) (0.305 g, 0.264 mmol) under argon. The reaction mixture was sealed and set stirring at 80° C. After complete consumption of starting material, the black mixture was diluted with water before extracting with dichloromethane, drying over sodium sulfate, filtering, and concentrating under reduced pressure to an orange oil, which was used without purification. MS (ESI, pos. ion) m/z: 308.0 (M+1).

Aufarbeitung

  1. customThe reaction mixture was sealed
  2. customAfter complete consumption of starting material
  3. additionthe black mixture was diluted with water
  4. extractionbefore extracting with dichloromethane
  5. dry with materialdrying over sodium sulfate
  6. filtrationfiltering
  7. concentrationconcentrating under reduced pressure to an orange oil, which
  8. customwas used without purification

Quellen und Nachweise

ORD-Eintrag
ord-531b8903f9fb45579fac7071e75520d7
Quelldatensatz
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08759532B2

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