Potassium Hydroxide → 4-[5-(2,6-diethyl-phenyl)-1H-pyrrolo[2,3-c]pyridine-3-yl]-cyclohex-3-enecarboxylic acid

HRID 472059

Reaktionsgleichung

Reaktionsgleichung von HRID 472059
[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][CH3:10])[C:4]=1[C:11]1[CH:12]=[C:13]2[CH:19]=[CH:18][NH:17][C:14]2=[CH:15][N:16]=1)[CH3:2].C[O:21][C:22]([CH:24]1[CH2:29][CH2:28][C:27](=O)[CH2:26][CH2:25]1)=[O:23].[OH-].[K+]>CO>[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][CH3:10])[C:4]=1[C:11]1[CH:12]=[C:13]2[C:19]([C:27]3[CH2:28][CH2:29][CH:24]([C:22]([OH:23])=[O:21])[CH2:25][CH:26]=3)=[CH:18][NH:17][C:14]2=[CH:15][N:16]=1)[CH3:2]

Komponenten

5

Edukt 3

HCID 14797Potassium HydroxideHCID 226643Methyl 4-oxocyclohexanecarboxylateHCID 116732465-(2,6-diethyl-phenyl)-1H-pyrrolo[2,3-c]pyridine

Produkt 1

HCID 671525894-[5-(2,6-diethyl-phenyl)-1H-pyrrolo[2,3-c]pyridine-3-yl]-cyclohex-3-enecarboxylic acidAusbeute 40,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel2×

Versuchsvorschrift

A solution of 5-(2,6-diethyl-phenyl)-1H-pyrrolo[2,3-c]pyridine (200 mg, 0.8 mmol) in MeOH (5 mL) is added to a stirring solution of 4-oxo-cyclohexanecarboxylic acid methyl ester (204 mg, 1.2 mmol) and KOH (163 mg, 2.9 mmol) in MeOH (10 mL) at room temperature. The mixture is heated at reflux for 24 hours. The solvent is removed to dryness in vacuo. The residue is mixed with water and adjusted pH to 7. The mixture is extracted with CH2Cl2 (2×10 mL). The organic layer is washed with brine, dried, and evaporated under reduce pressure to give 120 mg of crude product. The crude product is used for next step without further purification.

Aufarbeitung

  1. temperatureThe mixture is heated
  2. temperatureat reflux for 24 hours
  3. customThe solvent is removed to dryness in vacuo
  4. additionThe residue is mixed with water and adjusted pH to 7
  5. extractionThe mixture is extracted with CH2Cl2 (2×10 mL)
  6. washThe organic layer is washed with brine
  7. customdried
  8. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-4d13ef449e57435595c7e644a27df280
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08633193B2

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