Sodium Sulfite → 5-bromo-3-(1-ethyl-1H-imidazo[4,5-c]pyridin-2-yl)pyrazin-2-amine

HRID 1817152Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1817152
[CH2:1]([N:3]1[C:11]2[CH:10]=[CH:9][N:8]=[CH:7][C:6]=2[N:5]=[C:4]1[C:12]1[C:13]([NH2:18])=[N:14][CH:15]=[CH:16][N:17]=1)[CH3:2].[Br:19]N1C(=O)CCC1=O.S([O-])([O-])=O.[Na+].[Na+]>C1COCC1>[Br:19][C:16]1[N:17]=[C:12]([C:4]2[N:3]([CH2:1][CH3:2])[C:11]3[CH:10]=[CH:9][N:8]=[CH:7][C:6]=3[N:5]=2)[C:13]([NH2:18])=[N:14][CH:15]=1

Komponenten

5

Edukt 3

HCID 24437Sodium SulfiteHCID 67184N-bromobutanimideHCID 113568813-(1-ethyl-1H-imidazo[4,5-c]pyridin-2-yl)pyrazin-2-amine

Produkt 1

HCID 598524085-bromo-3-(1-ethyl-1H-imidazo[4,5-c]pyridin-2-yl)pyrazin-2-amineAusbeute 81,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 3-(1-ethyl-1H-imidazo[4,5-c]pyridin-2-yl)pyrazin-2-amine (0.45 g, 1.8 mmol) (see Example 1) in THF is added N-bromosuccinimide (0.37 g, 2.1 mmol). The reaction is stirred for 4 hours at ambient temperature. Sodium sulfite (excess) was added and stirred vigorously for 30 minutes. The mixture was then concentrated to dryness and treated with water. After sonication, the solids were collected on filter. Rinsing (×2) with diethyl ether afforded 5-bromo-3-(1-ethyl-1H-imidazo[4,5-c]pyridin-2-yl)pyrazin-2-amine (0.47 g, 79%) as tan solids.

Aufarbeitung

  1. stirringstirred vigorously for 30 minutes
  2. concentrationThe mixture was then concentrated to dryness
  3. additiontreated with water
  4. customAfter sonication
  5. customthe solids were collected
  6. filtrationon filter
  7. washRinsing (×2) with diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-a162716332a245e5866deae9181e4f02
Quelldatensatz
uspto-grants-2009_10
Patentnummer
US07598251B2

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