2-Chloroacetophenone → 2,3-Dimethyl-6-methylthio-7-phenacylpyrrolo[2,3-b]pyridine

HRID 1756071Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1756071
[CH3:1][C:2]1[NH:12][C:5]2=[N:6][C:7]([S:10][CH3:11])=[CH:8][CH:9]=[C:4]2[C:3]=1[CH3:13].[CH2:14](Cl)[C:15]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:16]>CC#N>[CH3:1][C:2]1[N:12]=[C:5]2[N:6]([CH2:14][C:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[O:16])[C:7]([S:10][CH3:11])=[CH:8][CH:9]=[C:4]2[C:3]=1[CH3:13]

Komponenten

4

Edukt 2

HCID 107572-ChloroacetophenoneHCID 193926102,3-Dimethyl-6-mehylthiopyrrolo[2,3-b]pyridine

Produkt 1

HCID 199168092,3-Dimethyl-6-methylthio-7-phenacylpyrrolo[2,3-b]pyridineAusbeute 41,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A mixture of 2,3-dimethyl-6-methylthiopyrrolo[2,3-b]pyridine (100 mg, 0.5 mmol) and phenacyl chloride (804 mg, 5 mmol) in 3 ml CH3CN was refluxed for 72 h. The solvent was evaporated and the residue chromatographed (silica, CH2Cl2 /MeOH;59/5). Pure fractions were pooled, evaporated, and taken up in 100 ml CH2Cl2. The organic layer was washed with 25 ml 2M HCl, dried over MgSO4, and evaporated leaving 64 mg (35%) pure product as the hydrochloride.

Aufarbeitung

  1. temperaturewas refluxed for 72 h
  2. customThe solvent was evaporated
  3. customthe residue chromatographed (silica, CH2Cl2 /MeOH;59/5)
  4. customevaporated
  5. washThe organic layer was washed with 25 ml 2M HCl
  6. dry with materialdried over MgSO4
  7. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-306b8c7de9b54e9a9f9a3526c70b58b8
Quelldatensatz
uspto-grants-1995_08
Patentnummer
US05439917

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