1,1'-Carbonyldiimidazole → 5-bromo-6-fluoro-1H-indole-7-carboxamide

HRID 656068Notes

Reaction equation

HRID 656068 reaction equation
C1N=C[N:3](C(N2C=NC=C2)=O)C=1.[Br:13][C:14]1[CH:15]=[C:16]2[C:20](=[C:21]([C:24]([OH:26])=O)[C:22]=1[F:23])[NH:19][CH:18]=[CH:17]2>C(Cl)Cl>[Br:13][C:14]1[CH:15]=[C:16]2[C:20](=[C:21]([C:24]([NH2:3])=[O:26])[C:22]=1[F:23])[NH:19][CH:18]=[CH:17]2

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 593327305-bromo-6-fluoro-1H-indole-7-carboxylic acid

Product 1

HCID 593326505-bromo-6-fluoro-1H-indole-7-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

CDI (0.7 g, 4.3 mmol) was added in portions to a stirred solution/suspension of 5-bromo-6-fluoro-1H-indole-7-carboxylic acid (1.0 g, 3.9 mmol) in DCM (20 mL). The mixture was stirred at room temperature for 1 hour and then heated at reflux for 30 min. The mixture was cooled in ice, and NH3 gas was bubbled through the solution for 30 min. The reaction mixture stirred at room temperature overnight. The resulting solid was filtered off and triturated sequentially with water, ether and IPA giving 260 mg (26%) of the title compound as a brown solid.

Workup

  1. temperatureheated
  2. temperatureat reflux for 30 min
  3. temperatureThe mixture was cooled in ice
  4. customNH3 gas was bubbled through the solution for 30 min
  5. stirringThe reaction mixture stirred at room temperature overnight
  6. filtrationThe resulting solid was filtered off
  7. customtriturated sequentially with water, ether and IPA giving 260 mg (26%) of the title compound as a brown solid

Sources & evidence

ORD record
ord-600d9a3552a046b28eb4dfe0e2d6c148
Source dataset
uspto-grants-2011_12
Patent number
US08071584B2

Reaction notes

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