N-bromobutanimide → 3-bromo-4-chloro-5-phenyl-1H-pyrrolo[2,3-b]pyridine

HRID 79551Notes

Reaction equation

HRID 79551 reaction equation
[Cl:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:6][N:5]=[C:4]2[NH:14][CH:15]=[CH:16][C:3]=12.[Br:17]N1C(=O)CCC1=O>C(Cl)(Cl)Cl.C(Cl)Cl>[Br:17][C:16]1[C:3]2[C:4](=[N:5][CH:6]=[C:7]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[C:2]=2[Cl:1])[NH:14][CH:15]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 687625794-chloro-5-phenyl-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 687633973-bromo-4-chloro-5-phenyl-1H-pyrrolo[2,3-b]pyridineYield 89.7%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

4-Chloro-5-phenyl-1H-pyrrolo[2,3-b]pyridine (0.912 g, 3.99 mmol) was placed in CHCl3 (5 mL) at room temperature. N-Bromosuccinimide (0.710 g, 3.99 mmol) was then added, and the reaction was stirred at room temperature for 1 hour. The reaction was diluted with DCM and washed with saturated NaHCO3. The organic fraction was dried, filtered, and concentrated to give the crude product 3-bromo-4-chloro-5-phenyl-1H-pyrrolo[2,3-b]pyridine (1.1 g, 89.7% yield).

Workup

  1. washwashed with saturated NaHCO3
  2. customThe organic fraction was dried
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-2e21514fcfb644c3a86a999ced72cf53
Source dataset
uspto-grants-2014_09
Patent number
US08841304B2

Reaction notes

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