Iodine → 7-iodo-2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazine

HRID 1677380Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1677380
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:13]2[N:14]=[C:15]3[CH:21]=[CH:20][NH:19][C:16]3=[N:17][CH:18]=2)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].[OH-].[K+].[I:24]I.S([O-])([O-])(=O)=S.[Na+].[Na+]>CN(C)C=O>[I:24][C:21]1[C:15]2[C:16](=[N:17][CH:18]=[C:13]([C:5]3[CH:6]=[C:7]([O:11][CH3:12])[C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=3)[N:14]=2)[NH:19][CH:20]=1

Komponenten

6

Edukt 4

HCID 807IodineHCID 14797Potassium HydroxideHCID 24477Sodium ThiosulfateHCID 595406852-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazine

Produkt 1

HCID 595405187-iodo-2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazineAusbeute 89,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a 0° C. mixture of 2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazine (2.4 g, 8.4 mmol) in dimethylformamide (30 ml) was added KOH (2 g, 36 mmol). After 20 min, iodine (3.2 g, 13 mmol) was added portionwise over 10 min and the reaction mixture was stirred for 4 h and poured into 0° C. saturated aqueous sodium thiosulfate (˜300 mL). Ice cold water (˜100 mL) was added and the resultant precipitate was collected, washed with water and dried in vacuo at 60° C. to afford 3.1 g (89%) of 7-iodo-2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazine as a brown solid. MP 230-232° C., M+H=412.

Aufarbeitung

  1. customthe resultant precipitate was collected
  2. washwashed with water
  3. customdried in vacuo at 60° C.

Quellen und Nachweise

ORD-Eintrag
ord-9d119185010c4dfca722b2e70a88b017
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US08008298B2

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