Cesium carbonate → 5-Bromo-3-(5-(4-Ethylpiperazin-1-yl)pyridin-2-ylamino)-1-methylpyridin-2(1H)-one

HRID 1918873Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1918873
[CH2:1]([N:3]1[CH2:8][CH2:7][N:6]([C:9]2[CH:10]=[CH:11][C:12]([NH2:15])=[N:13][CH:14]=2)[CH2:5][CH2:4]1)[CH3:2].Br[C:17]1[C:18](=[O:25])[N:19]([CH3:24])[CH:20]=[C:21]([Br:23])[CH:22]=1.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.C([O-])([O-])=O.[Cs+].[Cs+]>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].C(Cl)Cl.O1CCOCC1>[Br:23][C:21]1[CH:22]=[C:17]([NH:15][C:12]2[CH:11]=[CH:10][C:9]([N:6]3[CH2:5][CH2:4][N:3]([CH2:1][CH3:2])[CH2:8][CH2:7]3)=[CH:14][N:13]=2)[C:18](=[O:25])[N:19]([CH3:24])[CH:20]=1

Komponenten

8

Edukt 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 36143503,5-Dibromo-1-methylpyridin-2(1H)-oneHCID 284115995-(4-Ethylpiperazin-1-yl)pyridin-2-amine

Produkt 1

HCID 580436465-Bromo-3-(5-(4-Ethylpiperazin-1-yl)pyridin-2-ylamino)-1-methylpyridin-2(1H)-one

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 6344DichloromethaneLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a round-bottomed flask equipped with a stirring bar, 138b (2.52 g, 12.22 mmol), 3,5-dibromo-1-methylpyridin-2(1H)-one (4.89 g, 18.32 mmol), Pd2(dba)3 (1.12 g, 1.22 mmol), XantPhos (1.13 mg, 1.96 mmol), Cs2CO3 (13.14 g, 40.33 mmol) and dioxane (50 mL) were added. The reaction mixture was heated at 100° C. overnight. CH2Cl2 (200 mL) was added to the resulting mixture was washed with water (30 mL×3). CH2Cl2 (200 mL) was added and the resulting mixture was washed with water (30 mL×3), brine (30 mL×1), dried over MgSO4, filtered, and removed solvent in vacuo. CH2Cl2/ether (1:2, 5 mL) was added followed by sonication, the precipitation was filtered as 138c, a yellow solid, 2.718 g (57%).

Aufarbeitung

  1. customTo a round-bottomed flask equipped with a stirring bar
  2. washwas washed with water (30 mL×3)
  3. additionCH2Cl2 (200 mL) was added
  4. washthe resulting mixture was washed with water (30 mL×3), brine (30 mL×1)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customremoved solvent in vacuo
  8. additionCH2Cl2/ether (1:2, 5 mL) was added
  9. customfollowed by sonication
  10. customthe precipitation
  11. filtrationwas filtered as 138c

Quellen und Nachweise

ORD-Eintrag
ord-a91ff44924d944828948e72bed728689
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08618107B2

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