Cesium carbonate → HCID 59526288, Verbindung

HRID 386112

Reaktionsgleichung

Reaktionsgleichung von HRID 386112
Br[C:2]1[N:7]=[C:6]([Br:8])[CH:5]=[CH:4][N:3]=1.[CH3:9][N:10]([CH3:15])[S:11]([NH2:14])(=[O:13])=[O:12].C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O1CCOCC1>[Br:8][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([NH:14][S:11]([N:10]([CH3:15])[CH3:9])(=[O:13])=[O:12])[N:7]=1

Komponenten

7

Edukt 4

HCID 10796Cesium carbonateHCID 134472N,N-DimethylsulfamideHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 149763012,4-Dibromopyrimidine

Produkt 1

HCID 59526288HCID 59526288, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

2,4-Dibromopyrimidine (0.50 g, 2.11 mmol), N,N-dimethylsulfamide (0.26 mg, 2.11 mmol), cesium carbonate (2.75 g, 8.44 mmol), Pd2(dba)3 (0.10 mg, 0.11 mmol), and Xantphos (0.18 mg, 0.32 mmol) were placed in a flask. Dioxane (24 mL) was added and argon was bubbled through the solution for several minutes. The reaction was then heated at 100° C. overnight. The reaction was cooled to ambient temperature, diluted with ethyl acetate, washed with saturated sodium bicarbonate, dried over magnesium sulfate, filtered and concentrated. Reverse phase HPLC was used for purification to yield the title compound.

Aufarbeitung

  1. customargon was bubbled through the solution for several minutes
  2. temperatureThe reaction was cooled to ambient temperature
  3. additiondiluted with ethyl acetate
  4. washwashed with saturated sodium bicarbonate
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customReverse phase HPLC was used for purification

Quellen und Nachweise

ORD-Eintrag
ord-e19c56592412448cb3a2c0c46f28c929
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08367706B2

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