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

HRID 2075844Notes

Reaction equation

HRID 2075844 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-e4ceab7615b34ecc976f92719a93f796
Source dataset
uspto-grants-2011_04
Patent number
US07923466B2

Reaction notes

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