1,1'-Carbonyldiimidazole → 1H-Indole-2-carboxamide

HRID 1866229Notes

Reaction equation

HRID 1866229 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([OH:12])=O.C(N1C=CN=C1)([N:15]1C=CN=C1)=O>C1COCC1>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([NH2:15])=[O:12]

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 72899Indole-2-carboxylic acid

Product 1

HCID 5948321H-Indole-2-carboxamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Add to the 2-indole carboxylic acid (12.4 mmol) in anhydrous THF (30 ml), carbonyldiimidazole (1.5 equiv, 18.6 mmol) and stir for 1 h. Add the desired amine [for example, methylamine, ethylamine, dimethylamine, pyrrolidine, piperidine, piperazine, or morpholine, (3.0 equiv, 37.2 mmol)] in one portion and stir the reaction at rt. After 16 hours, quench the reaction with H2O, collect the resulting precipitate by filtration and dry under vacuum to afford the desired 2-indole carboxamide.

Workup

  1. stirringstir
  2. customthe reaction at rt
  3. waitAfter 16 hours
  4. customquench
  5. customthe reaction with H2O
  6. customcollect the resulting precipitate
  7. filtrationby filtration
  8. customdry under vacuum

Sources & evidence

ORD record
ord-2cc8235682de458781d179d31bba0a01
Source dataset
uspto-grants-2009_12
Patent number
US07629376B2

Reaction notes

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