Cesium carbonate → HCID 178496132, Verbindung

HRID 58178

Reaktionsgleichung

Reaktionsgleichung von HRID 58178
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:12]=[CH:11][C:9]([NH2:10])=[C:8]([N+:13]([O-:15])=[O:14])[CH:7]=1.Cl[C:17]1[N:22]=[CH:21][N:20]=[C:19]([NH:23]C)[CH:18]=1.[C:25]([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>C1(C)C=CC=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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].CO.C(Cl)Cl>[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:12]=[CH:11][C:9]([NH:10][C:17]2[CH:18]=[C:19]([NH2:23])[N:20]([CH3:25])[CH2:21][N:22]=2)=[C:8]([N+:13]([O-:15])=[O:14])[CH:7]=1

Komponenten

9

Edukt 4

HCID 10796Cesium carbonateHCID 3094796-chloro-N-methylpyrimidin-4-amineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 204787644-(2-Methoxyethoxy)-2-nitroaniline

Produkt 1

HCID 178496132HCID 178496132, VerbindungAusbeute 102,3 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 887MethanolLösungsmittelHCID 1140TolueneLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

4-(2-methoxyethoxy)-2-nitroaniline (0.6 g, 2.830 mmol) and 6-chloro-N-methylpyrimidin-4-amine (0.404 g, 2.830 mmol) were taken in 10 mL of dry toluene in a seal tube under Argon atmosphere at room temperature. The Argon gas purging was continued for additional 5-10 min. Then Cs2CO3 (2.3 g, 7.075 mmol, 2.5 eq) and Xantphos (0.490 g, 0.849 mmol) were added and the resulting reaction mixture was purged with argon gas for 5 min, followed by Pd2(dba)3 (0.518 g, 0.566 mmol) was added. The argon gas purging was continued for additional 5 min before sealing the reaction vial. Then the reaction mixture was heated at 100° C. for 7 h. After completion of the reaction by TLC (DCM:MeOH, 98:2), reaction mass was filtered through celite and the filtrate was evaporated under vacuum to get a crude residue. The crude residue was purified by column chromatography on silica gel to afford the title compound (0.93 g, yield: 70%); MS (ESI): 320.3 [M+H]+.

Aufarbeitung

  1. customThe Argon gas purging
  2. customthe resulting reaction mixture
  3. customwas purged with argon gas for 5 min
  4. additionwas added
  5. customThe argon gas purging
  6. waitwas continued for additional 5 min
  7. customAfter completion of the reaction
  8. filtrationwas filtered through celite
  9. customthe filtrate was evaporated under vacuum
  10. customto get a crude residue
  11. customThe crude residue was purified by column chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-10b134b340de4155a22735b085ebb7f5
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09434697B2

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