Potassium Cyanide → HCID 69093841, compound

HRID 2174279Notes

Reaction equation

HRID 2174279 reaction equation
Br[C:2]1[N:6]([CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[F:14])[N:5]=[C:4]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=2)[N:3]=1.[C-:21]#[N:22].[K+]>CN(C)C=O.C(OCC)(=O)C.O>[F:14][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[CH2:7][N:6]1[C:2]([C:21]#[N:22])=[N:3][C:4]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=2)=[N:5]1

Participants

6

Reactant 2

HCID 9032Potassium CyanideHCID 69094001HCID 69094001, compound

Product 1

HCID 69093841HCID 69093841, compoundYield 31%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 2-(5-bromo-1-(2-fluorobenzyl)-1H-1,2,4-triazol-3-yl)pyridine (I-16, 0.95 g, 2.9 mmol) in N,N-dimethylformamide (9.5 mL) was added potassium cyanide (0.928 g, 14.3 mmol). After heating the solution at 100° C. for 22 h, the solution was diluted with ethyl acetate (125 mL) and water (100 mL). The layers were separated, and the aqueous layer was extracted with ethyl acetate (2×50 mL). The organics were combined, washed with water (50 mL) and brine (50 mL), dried over magnesium sulfate, filtered, and the solvent was removed in vacuo to give the crude product as an orange oil. Purification by silica gel chromatography (0-15% ethyl acetate in dichloromethane) gave 1-(2-fluorobenzyl)-3-(pyridin-2-yl)-1H-1,2,4-triazole-5-carbonitrile, I-33 (250 mg, 0.90 mmol, 31% yield) as a white solid.

Workup

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted with ethyl acetate (2×50 mL)
  3. washwashed with water (50 mL) and brine (50 mL)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customthe solvent was removed in vacuo
  7. customto give the crude product as an orange oil
  8. customPurification by silica gel chromatography (0-15% ethyl acetate in dichloromethane)

Sources & evidence

ORD record
ord-95729f754c7e40b78e6c43fea2addaec
Source dataset
uspto-grants-2015_06
Patent number
US09061030B2

Reaction notes

Loading…