Potassium Fluoride → HCID 23373489, compound

HRID 864677Notes

Reaction equation

HRID 864677 reaction equation
[C:1]1([CH:7]([NH:14][C:15]([C:17]2[N:18]=[CH:19][NH:20][CH:21]=2)=[O:16])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F-].[K+].Br[CH:25]([CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[C:26]#[N:27]>CN(C)C=O>[CH2:28]([CH:25]([N:20]1[CH:21]=[C:17]([C:15]([NH:14][CH:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:16])[N:18]=[CH:19]1)[C:26]#[N:27])[CH2:29][CH2:30][CH2:31][CH2:32][CH3:33]

Participants

5

Reactant 3

HCID 522689Potassium FluorideHCID 11447037HCID 11447037, compoundHCID 178522803HCID 178522803, compound

Product 1

HCID 23373489HCID 23373489, compoundYield 49.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1.67 g of 4-{[(diphenylmethyl)amino]carbonyl}-1H-imidazole in 100 ml of dimethylformamide were added 5.03 g of potassium fluoride on alumina. With stirring, 1.35 g of α-bromo-octanonitrile were added. The solution was stirred at room temperature overnight and then concentrated in vacuo. The residue was taken up in ethyl acetate, washed with water, washed with a saturated sodium chloride solution, dried over magnesium sulfate, and concentrated in vacuo. NMR indicated a mixture of starting material with desired product, so the residue was dissolved in 200 ml of acetonitrile, and 1 g of α-bromooctanonitrile and 5 g of potassium fluoride on alumina was added. After stirring at room temperature for 2 days, the mixture was filtered, and the filtrate was concentrated in vacuo. The residue was chromatographed over SiO2 and the appropriate fractions combined and concentrated in vacuo to provide 1.2 g of the desired titled intermediate oil. MS: M+ =400

Workup

  1. stirringThe solution was stirred at room temperature overnight
  2. concentrationconcentrated in vacuo
  3. washwashed with water
  4. washwashed with a saturated sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. additiona mixture of starting material with desired product
  8. dissolutionso the residue was dissolved in 200 ml of acetonitrile
  9. addition1 g of α-bromooctanonitrile and 5 g of potassium fluoride on alumina was added
  10. stirringAfter stirring at room temperature for 2 days
  11. filtrationthe mixture was filtered
  12. concentrationthe filtrate was concentrated in vacuo
  13. customThe residue was chromatographed over SiO2
  14. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5436010912634b8fac5a39e37ead12b1
Source dataset
uspto-grants-1996_10
Patent number
US05563278

Reaction notes

Loading…