2-Chloro-4-iodo-6-(trifluoromethyl)pyridine → 2-Chloro-6-(trifluoromethyl)pyridine-4-carbonitrile

HRID 1426342Notes

Reaction equation

HRID 1426342 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](I)[CH:5]=[C:4]([C:9]([F:12])([F:11])[F:10])[N:3]=1.[Cu](C#N)[C:14]#[N:15]>CN1CCCC1=O.O.CCOC(C)=O>[Cl:1][C:2]1[CH:7]=[C:6]([CH:5]=[C:4]([C:9]([F:12])([F:11])[F:10])[N:3]=1)[C:14]#[N:15]

Participants

6

Reactant 2

HCID 108597852-Chloro-4-iodo-6-(trifluoromethyl)pyridineHCID 178418260HCID 178418260, compound

Product 1

HCID 534076042-Chloro-6-(trifluoromethyl)pyridine-4-carbonitrile

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
120 °C

Procedure

2-Chloro-4-iodo-6-(trifluoromethyl)pyridine (0.50 g, 1.5 mmol, prepared according to the method described in European Journal of Organic Chemistry, (18) 3793-3798; 2004) and copper cyanide (0.52 g, 5.8 mmol) were mixed in N-methylpyrrolidinone (2 mL). The reaction vial was sealed and heated in the microwave to 120° C. for 10 minutes. The mixture was diluted with water and EtOAc and was filtered. The organic layer was washed with water (3×), followed by brine, dried over sodium sulfate and concentrated. Flash chromatography on silica gel, eluting with a gradient from 0-15% EtOAc in hexanes afforded product as a colorless oil (0.24 g, 64%).

Workup

  1. customThe reaction
  2. customvial was sealed
  3. filtrationwas filtered
  4. washThe organic layer was washed with water (3×)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. washFlash chromatography on silica gel, eluting with a gradient from 0-15% EtOAc in hexanes afforded product as a colorless oil (0.24 g, 64%)

Sources & evidence

ORD record
ord-09015d6191954cba91623589767c9c92
Source dataset
uspto-grants-2015_01
Patent number
US08933085B2

Reaction notes

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