Potassium Carbonate → methyl 3-(5-cyano-1H-indol-3-yl)propanoate

HRID 1419611Notes

Reaction equation

HRID 1419611 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[CH:6]2)#[N:2].[C:12]([O-])([O-])=O.[K+].[K+].BrC[CH2:20][CH2:21][C:22]([O-:24])=[O:23]>C(#N)C.O>[CH3:12][O:24][C:22](=[O:23])[CH2:21][CH2:20][C:6]1[C:5]2[C:9](=[CH:10][CH:11]=[C:3]([C:1]#[N:2])[CH:4]=2)[NH:8][CH:7]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27513Indole-5-carbonitrileHCID 69936583-Bromomethylpropionate

Product 1

HCID 19921624methyl 3-(5-cyano-1H-indol-3-yl)propanoateYield 99.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of 5-cyanoindole (1.0 g, 7.0 mmol), K2CO3 (0.966 g, 7.0 mmol) in acetonitrile was added 3-bromomethylpropionate (1.17 g, 7.0 mmol). The mixture was stirred at reflux for 18 h under a nitrogen atmosphere, cooled, diluted with H2O, extracted with ethyl acetate, dried with Na2SO4, filtered and concentrated in vacuo to afford 1.59 g of product. 1H NMR (CD3OD) δ ppm 2.85 (t, 2H, J=6.6 Hz), 3.61 (s, 3H), 4.58 (t, 2H, J=6.6 Hz), 6.61 (s, 1H), 7.42, (m, 3H), 7.62 (d, 1H, J=8.4 Hz), 7.99 (s, 1H).

Workup

  1. temperatureat reflux for 18 h under a nitrogen atmosphere
  2. temperaturecooled
  3. extractionextracted with ethyl acetate
  4. dry with materialdried with Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d06fb9fce63240aabea36fe6fd18b2eb
Source dataset
uspto-grants-1999_03
Patent number
US05886191

Reaction notes

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