Potassium Carbonate → HCID 67086543, compound

HRID 1747219Notes

Reaction equation

HRID 1747219 reaction equation
C([O-])([O-])=O.[K+].[K+].F[C:8]1[C:15]([CH3:16])=[CH:14][CH:13]=[CH:12][C:9]=1[C:10]#[N:11].[NH:17]1[CH:21]=[CH:20][N:19]=[N:18]1>CN(C=O)C>[CH3:16][C:15]1[C:8]([N:18]2[N:19]=[CH:20][CH:21]=[N:17]2)=[C:9]([CH:12]=[CH:13][CH:14]=1)[C:10]#[N:11]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 231603592-Fluoro-3-methylbenzonitrileHCID 178418936HCID 178418936, compound

Product 1

HCID 67086543HCID 67086543, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

K2CO3 (8.18 g, 59.2 mmol) was added to a RT solution of 2-fluoro-3-methylbenzonitrile (4.0 g, 29.6 mmol) and 1H-1,2,3-triazole (1.72 mL, 29.6 mmol) in DMF (80 mL) and the resulting suspension was heated to 120° C. for 4 h. The reaction mixture was cooled to RT and quenched with water before being extracted with EtOAc (3×). The combined organic extracts were washed with brine, dried over Na2SO4, filtered and evaporated in vacuo to give the crude product that was purified by flash chromatography (eluting with a gradient of 33% to 50% EtOAc in hexane) to give 3-methyl-2-(2H-1,2,3-triazol-2-yl)benzonitrile as a white solid. LC-MS B: tR=0.62 min; [M+H]+=185.16.

Workup

  1. temperatureThe reaction mixture was cooled to RT
  2. customquenched with water
  3. extractionbefore being extracted with EtOAc (3×)
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customto give the crude product that
  9. customwas purified by flash chromatography (
  10. washeluting with a gradient of 33% to 50% EtOAc in hexane)

Sources & evidence

ORD record
ord-b23e6120b0254a5d9d497bf143a0c321
Source dataset
uspto-grants-2015_10
Patent number
US09150566B2

Reaction notes

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