Water → 4,6-dichloro-3-(4-(trifluoromethyl)benzyl)-3H-imidazo[4,5-c]pyridine

HRID 81079Notes

Reaction equation

HRID 81079 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([F:12])([F:11])[F:10])=[CH:5][CH:4]=1.[Cl:13][C:14]1[C:19]2[NH:20][CH:21]=[N:22][C:18]=2[CH:17]=[C:16]([Cl:23])[N:15]=1.C(=O)([O-])[O-].[Cs+].[Cs+].O>CC(N(C)C)=O>[Cl:13][C:14]1[C:19]2[N:20]([CH2:2][C:3]3[CH:8]=[CH:7][C:6]([C:9]([F:12])([F:11])[F:10])=[CH:5][CH:4]=3)[CH:21]=[N:22][C:18]=2[CH:17]=[C:16]([Cl:23])[N:15]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 1230621-(Bromomethyl)-4-(trifluoromethyl)benzeneHCID 178477826HCID 178477826, compound

Product 1

HCID 867244584,6-dichloro-3-(4-(trifluoromethyl)benzyl)-3H-imidazo[4,5-c]pyridine

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

1-(Bromomethyl)-4-(trifluoromethyl)benzene (6.36 g, 26.6 mmol) was added to a stirred solution of 4,6-dichloro-3H-imidazo[4,5-c]pyridine (5.0 g, 26.6 mmol) and cesium carbonate (10.40 g, 31.9 mmol) in DMA (30.0 ml) at room temperature and was stirred for 2 h. Water was added, and the solids were filtered and dried overnight. Crude 1H NMR showed ˜4:1 ratio of undesired 4,6-dichloro-1-(4-(trifluoromethyl)benzyl)-1H-imidazo[4,5-c]pyridine:desired 4,6-dichloro-3-(4-(trifluoromethyl)benzyl)-3H-imidazo[4,5-c]pyridine. The crude residue was purified by silica gel chromatography (EtOAc/DCM, 0% to 20%) to afford the desired 4,6-dichloro-3-(4-(trifluoromethyl)benzyl)-3H-imidazo[4,5-c]pyridine (fraction 1) and the undesired 4,6-dichloro-1-(4-(trifluoromethyl)benzyl)-1H-imidazo[4,5-c]pyridine (fraction 2). 4,6-dichloro-3-(4-(trifluoromethyl)benzyl)-3H-imidazo[4,5-c]pyridine: MS ESI calc'd for C14H8Cl2F3N3 [M+H]+ 346. found 346.

Workup

  1. filtrationthe solids were filtered
  2. customdried overnight
  3. customThe crude residue was purified by silica gel chromatography (EtOAc/DCM, 0% to 20%)

Sources & evidence

ORD record
ord-fc288d588c5840589218e06a2b425612
Source dataset
uspto-grants-2014_09
Patent number
US08846657B2

Reaction notes

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