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Cesium carbonate → 2-[(tert-Butyldimethylsilanyl)oxymethyl]phenyl-2-chloroimidazo[1,2-a]pyridine

HRID 2196442
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2196442
Br[C:2]1[CH:16]=[CH:15][CH:14]=[CH:13][C:3]=1[CH2:4][O:5][Si:6]([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7].[Cl:17][C:18]1[N:19]=[C:20]2[CH:25]=[CH:24][C:23](B3OC(C)(C)C(C)(C)O3)=[CH:22][N:21]2[CH:35]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCCC1.O>[Si:6]([O:5][CH2:4][C:3]1[CH:13]=[CH:14][CH:15]=[CH:16][C:2]=1[C:35]1[N:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]2=[N:19][C:18]=1[Cl:17])([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7]
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Komponenten

6

Edukt 3

HCID 10796Cesium carbonateHCID 13424900(2-Bromobenzyloxy)tert-butyldimethylsilaneHCID 442323732-Chloro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)imidazo[1,2-a]pyridine

Produkt 1

HCID 866520702-[(tert-Butyldimethylsilanyl)oxymethyl]phenyl-2-chloroimidazo[1,2-a]pyridineAusbeute 46,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962
Water
Lösungsmittel
HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

450 mg of (2-bromobenzyloxy)-tert-butyldimethylsilane, 500 mg of 2-chloro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)imidazo[1,2-a]pyridine and 1.46 g of caesium carbonate are dissolved in 8 ml of tetrahydrofuran and 1 ml of water. The mixture is degassed with argon for 10 min, 110 mg of [1,1′-bis(diphenylphosphino)-ferrocene]dichloropalladium are added and the mixture is heated at the reflux of the solvent for 16 hours. After cooling, the reaction mixture is hydrolysed with water, and the organic phase, which has been extracted with dichloromethane, is separated, dried and concentrated under reduced pressure. The oil obtained is purified by silica gel chromatography, elution being carried out with a heptane/ethyl acetate mixture. 260 mg of compound are obtained.

Aufarbeitung

  1. customThe mixture is degassed with argon for 10 min
  2. addition110 mg of [1,1′-bis(diphenylphosphino)-ferrocene]dichloropalladium are added
  3. temperaturethe mixture is heated at the
  4. temperaturereflux of the solvent for 16 hours
  5. temperatureAfter cooling
  6. extractionthe organic phase, which has been extracted with dichloromethane
  7. customis separated
  8. customdried
  9. concentrationconcentrated under reduced pressure
  10. customThe oil obtained
  11. customis purified by silica gel chromatography, elution

Quellen und Nachweise

ORD-Eintrag
ord-d9717c96f6fc459b91c5f9e7127a7d55
Quelldatensatz
uspto-grants-2012_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08338451B2

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