Potassium Carbonate → HCID 18950378, compound

HRID 248834Notes

Reaction equation

HRID 248834 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2.F[C:12]1[CH:19]=[CH:18][CH:17]=[CH:16][C:13]=1[C:14]#[N:15].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O>[CH3:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][N:6]2[C:12]1[CH:19]=[CH:18][CH:17]=[CH:16][C:13]=1[C:14]#[N:15]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 678552-FluorobenzonitrileHCID 852824-Methylindole

Product 1

HCID 18950378HCID 18950378, compoundYield 85.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

4-Methyl-1H-indole (1.042 g, 7.94 mmol, 1.0 eq) was combined with 2-fluoro-benzonitrile (1.29 mL, 11.91 mmol, 1.5 eq) and potassium carbonate (2.195 g, 15.88 mmol, 2.0 eq) in DMF (7.94 mL, 1M) and heated at 150° C. for 4 hours. The reaction was then cooled to room temperature, diluted with water (20 mL), and extracted three times with ethyl acetate. The organic extracts were washed with water and aqueous saturated sodium chloride, dried over sodium sulfate, filtered through magnesium sulfate and concentrated. The residue was chromatographed on Merck silica gel (50 g) eluting with chloroform:hexane (1:3) followed by (1:1) to give the title compound (1.57 g, 85%).

Workup

  1. temperatureThe reaction was then cooled to room temperature
  2. extractionextracted three times with ethyl acetate
  3. washThe organic extracts were washed with water and aqueous saturated sodium chloride
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered through magnesium sulfate
  6. concentrationconcentrated
  7. customThe residue was chromatographed on Merck silica gel (50 g)
  8. washeluting with chloroform:hexane (1:3)

Sources & evidence

ORD record
ord-5cbf937d0ef34b33af2f6584a8409b35
Source dataset
uspto-grants-1993_05
Patent number
US05212177

Reaction notes

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