Trim → HCID 86640018, compound

HRID 1673054Notes

Reaction equation

HRID 1673054 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH:13]=[CH:12][N:11]=[CH:10]1.[C-:16]#[N:17].[Na+]>CN(C=O)C>[F:15][C:2]([F:14])([F:1])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH:13]=[C:12]([C:16]#[N:17])[N:11]=[CH:10]1

Participants

4

Reactant 2

HCID 1359TrimHCID 8929Sodium Cyanide

Product 1

HCID 86640018HCID 86640018, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4-(chloromethyl)-1-(3′-methylsulfonyl)biphenyl-4-yl)-2-(2-(trifluoromethyl)phenyl-1H-imidazole (1.1 g), NaCN (1.2 g, 24.5 mmol), and dry DMF was stirred at 100° C. for 12 h. The solvent was removed in vacuo, and the residue was partitioned between water and EtOAc, the phases were separated, and the aqueous phase was extracted with EtOAc. The combined extracts were washed with water, brine, dried over sodium sulfate, and evaporated in vacuo. The crude product was purified by flash chromatography (SiO2, 80% EtOAc/hexanes) to give 1-(1-(3′-methylsulfonyl)biphenyl-4-yl)-2-(2-(trifluoromethyl)phenyl-1H-imidazole-4-carbonitrile (730 mg, 74%) as a white solid. MS (ESI) 482 [M+H]+.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was partitioned between water and EtOAc
  3. customthe phases were separated
  4. extractionthe aqueous phase was extracted with EtOAc
  5. washThe combined extracts were washed with water, brine
  6. dry with materialdried over sodium sulfate
  7. customevaporated in vacuo
  8. customThe crude product was purified by flash chromatography (SiO2, 80% EtOAc/hexanes)

Sources & evidence

ORD record
ord-e59ec636424f4c2e82ac6dc5852c50cf
Source dataset
uspto-grants-2011_08
Patent number
US07998995B2

Reaction notes

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