HCID 58877903, compound → HCID 58877898, compound

HRID 1664190Notes

Reaction equation

HRID 1664190 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C:9]1[N:13]([CH3:14])[N:12]=[CH:11][N:10]=1.[Cu][C:16]#[N:17]>CN(C)C=O>[F:8][C:5]1[CH:6]=[CH:7][C:2]([C:16]#[N:17])=[C:3]([C:9]2[N:13]([CH3:14])[N:12]=[CH:11][N:10]=2)[CH:4]=1

Participants

4

Reactant 2

HCID 58877903HCID 58877903, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 58877898HCID 58877898, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 5-(2-bromo-5-fluorophenyl)-1-methyl-1H-1,2,4-triazole (1.85 g, 7.22 mmol) in N,N-dimethylformamide (10 ml) was treated with copper (I) cyanide (0.71 g, 7.95 mmol). The mixture was then maintained under vacuum for a few minutes, flushed with argon and heated at 100° C. for 16 h. The solvent was then evaporated in vacuo and the residual oil was diluted with ethyl acetate and washed with a solution of 10% ammonium hydroxide followed by 20% ammonium chloride in water. The organic fraction was then washed with brine, dried over anhydrous magnesium sulfate and concentrated. Column chromatography of the residue on silica gel (elution gradient ethyl acetate 0-40% in toluene) gave 1.09 g (75% yield) of the title nitrile as white crystals: mp 134° C. (ethyl acetate-hexane). 1HNMR 400 MHz (CDCl3) δ (ppm): 3.98 (3H, s, CH3), 7.37-7.42 (2H, m, aromatics), 7.90 (1H, dd, J=5.0 Hz and J=8.6 Hz, aromatic), 8.08 (1H, s, CH). Anal. Calcd for C10H7FN4: C 59.40, H 3.49, N 27.71; Found: C 59.22, H 3.28, N 27.68.

Workup

  1. temperatureThe mixture was then maintained under vacuum for a few minutes
  2. customflushed with argon
  3. customThe solvent was then evaporated in vacuo
  4. additionthe residual oil was diluted with ethyl acetate
  5. washwashed with a solution of 10% ammonium hydroxide
  6. washThe organic fraction was then washed with brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-c7a464a945d647ce9d4dfadd79edcd59
Source dataset
uspto-grants-2011_10
Patent number
US08039458B2

Reaction notes

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