2,4-Dimethoxybenzylamine → 3-Chloro-7-[[(2,4-dimethoxyphenyl)methyl]amino]-5H-benzo[4,5]cyclohepta[1,2-b]pyridin-5-one

HRID 1987086Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1987086
Br[C:2]1[CH:3]=[CH:4][C:5]2[CH:16]=[CH:15][C:9]3=[N:10][CH:11]=[C:12]([Cl:14])[CH:13]=[C:8]3[C:7](=[O:17])[C:6]=2[CH:18]=1.C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(C)([O-])C.[Na+].[CH3:71][O:72][C:73]1[CH:80]=[C:79]([O:81][CH3:82])[CH:78]=[CH:77][C:74]=1[CH2:75][NH2:76]>[Pd].[Pd].C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.O1CCOCC1>[Cl:14][C:12]1[CH:13]=[C:8]2[C:7](=[O:17])[C:6]3[CH:18]=[C:2]([NH:76][CH2:75][C:74]4[CH:77]=[CH:78][C:79]([O:81][CH3:82])=[CH:80][C:73]=4[O:72][CH3:71])[CH:3]=[CH:4][C:5]=3[CH:16]=[CH:15][C:9]2=[N:10][CH:11]=1

Komponenten

7

Edukt 4

HCID 5972502,4-DimethoxybenzylamineHCID 634876Binap, (A+-)-HCID 159808187-Bromo-3-chloro-5H-benzo[4,5]cyclohepta[1,2-B]pyridin-5-oneHCID 23676156Sodium t-butoxide

Produkt 1

HCID 159808203-Chloro-7-[[(2,4-dimethoxyphenyl)methyl]amino]-5H-benzo[4,5]cyclohepta[1,2-b]pyridin-5-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9832798Tris(dibenzylideneacetone) dipalladiumKatalysatorHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

7-bromo-3-chloro-5H-benzo[4,5]cyclohepta[1,2-b]pyridin-5-one (3.0 g, 9.40 mmol), tris(dibenzylideneacetone) dipalladium (0) (Pd2(dba3)) (43 mg, 0.047 mmol), rac-2,2′-bis(diphenylphosphino)-1,1′-binapthyl (BINAP) (88 mg, 0.141 mmol), and sodium tert-butoxide (1.08 g, 11.3 mmol) were combined in a dry flask through which argon was purged. The flask was charged with 100 mL of dry dioxane, 2,4-dimethoxybenzylamine (1.41 mL, 9.40 mmol) was added, and the mixture was sparged with argon for 5 minutes. The reaction was heated to 100° C. and stirred under argon. After 2 h the reaction was concentrated and dissolved in 400 ml of ethyl acetate and washed with 100 mL of saturated aqueous ammonium chloride solution. The organic layer was separated, dried with magnesium sulfate, filtered, and concentrated. The resultant solids were slurried in 50 mL hot methanol, then allowed to cool to ambient temperature. The solids were filtered and dried to afford the title compound. LRMS (APCI) calculated for C23H20ClN2O3 [M+H]+, 407.1; found 407.1.

Aufarbeitung

  1. customwas purged
  2. additionwas added
  3. customthe mixture was sparged with argon for 5 minutes
  4. concentrationAfter 2 h the reaction was concentrated
  5. dissolutiondissolved in 400 ml of ethyl acetate
  6. washwashed with 100 mL of saturated aqueous ammonium chloride solution
  7. customThe organic layer was separated
  8. dry with materialdried with magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated
  11. temperatureto cool to ambient temperature
  12. filtrationThe solids were filtered
  13. customdried

Quellen und Nachweise

ORD-Eintrag
ord-93a3c1d817ba4338b09fab32741d76c2
Quelldatensatz
uspto-grants-2009_06
Patentnummer
US07550478B2

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