Water → 6-(3-chloro-4-hydroxy-5-trifluoromethyl-phenyl)-1-methyl-1H-imidazo[4,5-c]pyridine-4-carbonitrile

HRID 2079556Notes

Reaction equation

HRID 2079556 reaction equation
[Cl:1]N1C(=O)CCC1=O.[OH:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[N:21]=[C:20]([C:22]#[N:23])[C:19]3[N:24]=[CH:25][N:26]([CH3:27])[C:18]=3[CH:17]=2)=[CH:12][C:11]=1[C:28]([F:31])([F:30])[F:29].C(OCC)(=O)C.O>CN(C=O)C>[Cl:1][C:15]1[CH:14]=[C:13]([C:16]2[N:21]=[C:20]([C:22]#[N:23])[C:19]3[N:24]=[CH:25][N:26]([CH3:27])[C:18]=3[CH:17]=2)[CH:12]=[C:11]([C:28]([F:31])([F:30])[F:29])[C:10]=1[OH:9]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 31398ChlorosuccinimideHCID 1360110856-(4-Hydroxy-3-trifluoromethyl-phenyl)-1-methyl-1H-imidazo[4,5-c]pyridine-4-carbonitrile

Product 1

HCID 1361890446-(3-chloro-4-hydroxy-5-trifluoromethyl-phenyl)-1-methyl-1H-imidazo[4,5-c]pyridine-4-carbonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-Chlorosuccinimide (84 mg) was added to a solution of 6-(4-hydroxy-3-trifluoromethyl-phenyl)-1-methyl-1H-imidazo[4,5-c]pyridine-4-carbonitrile (200 mg) in DMF (4 ml). The mixture was stirred at room temperature for 24 hours, then ethyl acetate (50 ml) and water (20 ml) were added and the organic layer was washed twice with water (2×20 ml) and brine (20 ml), then dried over sodium sulfate, filtered and concentrated under reduced pressure to afford a crude (165 mg) with 6-(3-chloro-4-hydroxy-5-trifluoromethyl-phenyl)-1-methyl-1H-imidazo[4,5-c]pyridine-4-carbonitrile which is contaminated starting material. This material was used for next step without further purification.

Workup

  1. washthe organic layer was washed twice with water (2×20 ml) and brine (20 ml)
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3c758dbfa9cd4b6e83e2bb48d895e494
Source dataset
uspto-grants-2011_04
Patent number
US07932251B2

Reaction notes

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