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Water → HCID 11182227, Verbindung

HRID 1826243
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1826243
Br[C:2]1[N:7]=[C:6]([NH:8][C:9](=[O:14])[C:10]([CH3:13])([CH3:12])[CH3:11])[CH:5]=[CH:4][CH:3]=1.Cl[P:16]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.O>C(OCC)C>[C:23]1([P:16]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:2]2[N:7]=[C:6]([NH:8][C:9](=[O:14])[C:10]([CH3:13])([CH3:12])[CH3:11])[CH:5]=[CH:4][CH:3]=2)[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 962WaterHCID 66180ChlorodiphenylphosphineHCID 9921361N-(6-Bromopyridin-2-yl)-2,2-dimethylpropanamide

Produkt 1

HCID 11182227HCID 11182227, VerbindungAusbeute 27 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

1.00 g (3.89 mmol) of 6-bromo-2-pivaloylaminopyridine from example 14.2.1 was dissolved in 10 ml of diethyl ether and admixed at 0° C. with 3.64 ml (8.00 mmol) of (iso-C3H7)MgBr (2.2M in Et2O). The suspension was stirred at 0° C. for 18 h and then admixed with 0.7 ml (0.86 g, 3.89 mmol) of chlorodiphenylphosphine. The mixture was allowed to warm to ambient temperature overnight and was then hydrolyzed by adding 10 ml of dist. H2O. The resulting phases were separated and the aqueous phase was extracted twice with 50 ml each time of ethyl acetate. The organic phases were combined and dried over Na2SO4, and the solvent was removed under reduced pressure. The residue was filtered together with dichloromethane through a short silica gel column (2×10 cm) and the solvent was removed under reduced pressure. The resulting oil was crystallized by digesting with petroleum ether/diethyl ether (40/60). The crystals were filtered off and washed with petroleum ether/diethyl ether (40/60). 0.38 g (1.05 mmol, 27.0%) of 6-(diphenylphosphino)-2-pivaloylaminopyridine was obtained as a solid.

Aufarbeitung

  1. temperatureto warm to ambient temperature overnight
  2. additionby adding 10 ml of dist
  3. customThe resulting phases were separated
  4. extractionthe aqueous phase was extracted twice with 50 ml each time of ethyl acetate
  5. dry with materialdried over Na2SO4
  6. customthe solvent was removed under reduced pressure
  7. filtrationThe residue was filtered together with dichloromethane through a short silica gel column (2×10 cm)
  8. customthe solvent was removed under reduced pressure
  9. customThe resulting oil was crystallized
  10. filtrationThe crystals were filtered off
  11. washwashed with petroleum ether/diethyl ether (40/60)

Quellen und Nachweise

ORD-Eintrag
ord-9e9bf29279814d65b7d779cb73d725ca
Quelldatensatz
uspto-grants-2006_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07049473B2

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