Water → 6-chloro-3-(6-chloropyrazin-2-yl)-3H-imidazo[4,5-c]pyridine 6-chloro-1-(6-chloropyrazin-2-yl)-1H-imidazo[4,5-c]pyridine

HRID 1896207Notes

Reaction equation

HRID 1896207 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]2[NH:8][CH:9]=[N:10][C:4]=2[CH:3]=1.[Cl:11][C:12]1[CH:17]=[N:16][CH:15]=[C:14]([Cl:18])[N:13]=1.[F-].[Cs+].O>CS(C)=O>[Cl:1][C:2]1[N:7]=[CH:6][C:5]2[N:8]([C:14]3[CH:15]=[N:16][CH:17]=[C:12]([Cl:11])[N:13]=3)[CH:9]=[N:10][C:4]=2[CH:3]=1.[Cl:1][C:2]1[N:7]=[CH:6][C:5]2[N:8]=[CH:9][N:10]([C:12]3[CH:17]=[N:16][CH:15]=[C:14]([Cl:18])[N:13]=3)[C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 25953Cesium fluorideHCID 785042,6-DichloropyrazineHCID 218138956-Chloro-3H-imidazo(4,5-c)pyridine

Product 1

HCID 866543176-chloro-3-(6-chloropyrazin-2-yl)-3H-imidazo[4,5-c]pyridine 6-chloro-1-(6-chloropyrazin-2-yl)-1H-imidazo[4,5-c]pyridine

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 6-chloro-3H-imidazo[4,5-c]pyridine (4.6 g, 30 mmol), 2,6-dichloropyrazine (6 g, 40.5 mmol) and CsF (9.1 g, 60 mmol) in dry DMSO (80 mL) was stirred at room temperature for 20 h under N2. The mixture was poured into water (50 mL) with stirring. The formed precipitate was collected by filtration. The filter cake was suspended in MeOH (20 mL) and filtered again. The filter cake was collected and dried in vacuum which gave a mixture of title compounds 18a & 17a as a white solid (5.0 g, 62.9%).

Workup

  1. stirringwith stirring
  2. filtrationThe formed precipitate was collected by filtration
  3. filtrationfiltered again
  4. customThe filter cake was collected
  5. customdried in vacuum which
  6. customgave

Sources & evidence

ORD record
ord-46677eac6d294294a28584219bfc6d41
Source dataset
uspto-grants-2013_08
Patent number
US08518952B2

Reaction notes

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