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2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 1-(2,4-dichlorophenyl)-2-(4-hydroxyphenyl)-3-methyl-5-piperidin-1-yl-1,5-dihydro-4H-pyrrolo[3,2-c]pyridin-4-one

HRID 2102874
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2102874
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:17]2[CH2:16][CH2:15][N:14]([N:18]3[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]3)[C:13](=[O:24])[C:12]=2[C:11]([CH3:25])=[C:10]1[C:26]1[CH:31]=[CH:30][C:29]([OH:32])=[CH:28][CH:27]=1.C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N>O1CCOCC1>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:17]2[CH:16]=[CH:15][N:14]([N:18]3[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]3)[C:13](=[O:24])[C:12]=2[C:11]([CH3:25])=[C:10]1[C:26]1[CH:27]=[CH:28][C:29]([OH:32])=[CH:30][CH:31]=1
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Komponenten

4

Edukt 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 166661651-(2,4-Dichlorophenyl)-2-(4-hydroxyphenyl)-3-methyl-5-piperidin-1-yl-1,5,6,7-tetrahydro-pyrrolo[3,2-c]pyridine-4-one

Produkt 1

HCID 578035911-(2,4-dichlorophenyl)-2-(4-hydroxyphenyl)-3-methyl-5-piperidin-1-yl-1,5-dihydro-4H-pyrrolo[3,2-c]pyridin-4-oneAusbeute 49 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-Dioxane
Lösungsmittel

Versuchsvorschrift

A suspension of 1-(2,4-dichlorophenyl)-2-(4-hydroxyphenyl)-3-methyl-5-piperidin-1-yl-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one (153 mg, 0.325 mmol) and DDQ (295 mg, 1.301 mmol) in 1,4-dioxane (12 ml) was stirred at rt for 1 h and 20 min followed by 1 h and 50 min at 35° C. and 2 h and 50 min at 45° C. The solvent was evaporated and the product purified by hplc. The solvent was evaporated and water added. The product was extracted from the water phase with DCM and EtOAc. The combined organic phases were evaporated and the residue was re-suspended in toluene and evaporated to yield the product as a yellow solid (74 mg, 49%). MS m/z 468 (M+H)+.

Aufarbeitung

  1. waitfollowed by 1 h and 50 min at 35° C. and 2 h and 50 min at 45° C
  2. customThe solvent was evaporated
  3. customthe product purified by hplc
  4. customThe solvent was evaporated
  5. additionwater added
  6. extractionThe product was extracted from the water phase with DCM and EtOAc
  7. customThe combined organic phases were evaporated
  8. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-24c20c684d464bbf9755b32c204ad5ad
Quelldatensatz
uspto-grants-2009_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07576095B2

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