Potassium Carbonate → HCID 86658616, Verbindung

HRID 1517000Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1517000
[Cl:1][C:2]1[C:7]([N:8]=P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[C:6](I)[CH:5]=[CH:4][N:3]=1.[CH3:29][O:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1B(O)O.C(=O)([O-])[O-].[K+].[K+]>COCCOC.[Pd].P.P.P.P>[Cl:1][C:2]1[C:7]([NH2:8])=[C:6]([C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=2[O:30][CH3:29])[CH:5]=[CH:4][N:3]=1

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 27339582-Methoxyphenylboronic acidHCID 58479601HCID 58479601, Verbindung

Produkt 1

HCID 86658616HCID 86658616, VerbindungAusbeute 78,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 86658617HCID 86658617, VerbindungKatalysatorHCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

2-chloro-4-iodo-N-(triphenylphosphoranylidene) pyridin-3-amine (12 g, 23 mmol), (2-methoxyphenyl) boronic acid (4.25 g, 28 mmol), 2M potassium carbonate solution (46.6 ml, 93 mmol) were poured in 120 mL DME and degassed with bubbling nitrogen for 15 min. To the stirred solution was added tetrakisphosphine palladium(0) (1.35 g, 1.12 mmol) and reaction mixture was degassed for another 10 min. Reaction mixture was then refluxed for 48 h. Cooled reaction mixture was partitioned between ethyl acetate and brine. Organic layer was isolated, dried over anhd. Na2SO4 and purified by silica gel column chromatography using 5-30% ethyl acetate/hexanes as eluent. 2-chloro-4-(2-methoxyphenyl)pyridin-3-amine (4.3 g, 18 mmol, 78% yield) was isolated as liquid oil which turns into white crystals upon standing at room temperature.

Aufarbeitung

  1. customdegassed with bubbling nitrogen for 15 min
  2. additionTo the stirred solution was added
  3. customwas degassed for another 10 min
  4. customReaction mixture
  5. temperaturewas then refluxed for 48 h
  6. temperatureCooled
  7. customreaction mixture
  8. customwas partitioned between ethyl acetate and brine
  9. customOrganic layer was isolated
  10. customdried over anhd
  11. customNa2SO4 and purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-40bbc5aaf6b64f6aad46ddabc68ad8f9
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08227801B2

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