N,N'-Dimethylethylenediamine → 5-(1H-1,2,4-triazol-1-yl)-1H-indole

HRID 1467999Notes

Reaction equation

HRID 1467999 reaction equation
I[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.[NH:11]1[CH:15]=[N:14][CH:13]=[N:12]1.C([O-])([O-])=O.[K+].[K+].N1CCC[C@H]1C(O)=O.CNCCNC>CN(C=O)C.[Cu]I>[N:11]1([C:2]2[CH:3]=[C:4]3[C:8](=[CH:9][CH:10]=2)[NH:7][CH:6]=[CH:5]3)[CH:15]=[N:14][CH:13]=[N:12]1

Participants

8

Reactant 5

HCID 8070N,N'-DimethylethylenediamineHCID 92571H-1,2,4-TriazoleHCID 11430Potassium CarbonateHCID 145742L-ProlineHCID 27823135-Iodo-1H-indole

Product 1

HCID 676168785-(1H-1,2,4-triazol-1-yl)-1H-indoleYield 58%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

To a stirred solution of 5-iodo-1H-indole (2.0 g, 8.2 mmol), 1H-1,2,4-triazole (0.511 g, 7.4 mmol), CuI (0.15 g, 0.82 mmol), K2CO3 (2.27 g, 16.46 mmol) and L-proline (0.511 g, 7.4 mmol) in DMF (20 mL), N,N′-dimethylethylenediamine (2.375 g 16.46 mmol) was added and stirred at 120° C. for 2-3 h. The reaction was quenched with water and the mixture was extracted with ethyl acetate. The organic layer was separated, concentrated in vacuo and the residue was purified by flash column chromatography to give 5-(1H-1,2,4-triazol-1-yl)-1H-indole (0.790 g, 52%); MS: 185 (M+1).

Workup

  1. customThe reaction was quenched with water
  2. extractionthe mixture was extracted with ethyl acetate
  3. customThe organic layer was separated
  4. concentrationconcentrated in vacuo
  5. customthe residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-4f4f52c3c0214823a0b208054a14cf68
Source dataset
uspto-grants-2015_04
Patent number
US09000175B2

Reaction notes

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