N-bromobutanimide → 3-bromo-5-(2,6-diethyl-phenyl)-1-(4-isopropyl-phenyl)-1H-pyrrolo[2,3-c]pyridine

HRID 472033Notes

Reaction equation

HRID 472033 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][CH3:10])[C:4]=1[C:11]1[CH:12]=[C:13]2[CH:19]=[CH:18][N:17]([C:20]3[CH:25]=[CH:24][C:23]([CH:26]([CH3:28])[CH3:27])=[CH:22][CH:21]=3)[C:14]2=[CH:15][N:16]=1)[CH3:2].C1C(=O)N([Br:36])C(=O)C1>C(Cl)Cl>[Br:36][C:19]1[C:13]2[C:14](=[CH:15][N:16]=[C:11]([C:4]3[C:5]([CH2:9][CH3:10])=[CH:6][CH:7]=[CH:8][C:3]=3[CH2:1][CH3:2])[CH:12]=2)[N:17]([C:20]2[CH:25]=[CH:24][C:23]([CH:26]([CH3:28])[CH3:27])=[CH:22][CH:21]=2)[CH:18]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 582699455-(2,6-diethyl-phenyl)-1-(4-isopropyl-phenyl)-1H-pyrrolo[2,3-c]pyridine

Product 1

HCID 671527283-bromo-5-(2,6-diethyl-phenyl)-1-(4-isopropyl-phenyl)-1H-pyrrolo[2,3-c]pyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-(2,6-diethyl-phenyl)-1-(4-isopropyl-phenyl)-1H-pyrrolo[2,3-c]pyridine (2.36 g, 6.4 mmol) in DCM (50 mL), NBS (1.25 g, 7.0 mmol) is added and the mixture is stirred at room temperature for 1 h. The mixture is concentrated under reduced pressure, and the product is dissolved in a 5:1 EtOAc/Hexane mixture and filtered over a small pad of silica gel. The solvent is removed under reduced pressure to afford 3-bromo-5-(2,6-diethyl-phenyl)-1-(4-isopropyl-phenyl)-1H-pyrrolo[2,3-c]pyridine.

Workup

  1. concentrationThe mixture is concentrated under reduced pressure
  2. dissolutionthe product is dissolved in a 5:1 EtOAc/Hexane mixture
  3. filtrationfiltered over a small pad of silica gel
  4. customThe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-59a134be37324d65bddbcb9542588d3d
Source dataset
uspto-grants-2014_01
Patent number
US08633193B2

Reaction notes

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