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

HRID 2373167Notes

Reaction equation

HRID 2373167 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

HCID 598524085-bromo-3-(1-ethyl-1H-imidazo[4,5-c]pyridin-2-yl)pyrazin-2-amineYield 81.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-61f47a47ab4e40f2ad2c5926ec2d94c8
Source dataset
uspto-grants-2008_12
Patent number
US07459454B2

Reaction notes

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