Potassium Hydroxide → HCID 67959999, compound

HRID 1529298Notes

Reaction equation

HRID 1529298 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][CH:13]=[CH:12]2.[OH-].[K+].C1C(=O)N([Br:27])C(=O)C1>CN(C=O)C.O>[Br:27][C:12]1[C:11]2[C:15](=[CH:16][CH:17]=[C:9]([C:3]3[C:2]([F:1])=[CH:7][CH:6]=[CH:5][C:4]=3[F:8])[CH:10]=2)[NH:14][CH:13]=1

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 67184N-bromobutanimideHCID 67958183HCID 67958183, compound

Product 1

HCID 67959999HCID 67959999, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 5-(2,6-difluorophenyl)-1H-indole (2.0 g, 8.7 mmol) in DMF (20 mL) was added KOH (0.98 g, 17.5 mmol) and NBS (1.55 g, 8.7 mmol) at RT and stirred for 1 h. The resulting mixture was diluted with water, extracted with DCM (20 mL), dried over Na2SO4, filtered, concentrated to give crude 3-bromo-5-(2,6-difluorophenyl)-1H-indole.

Workup

  1. extractionextracted with DCM (20 mL)
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-21855a12ff714daaa63edd0e26bd992c
Source dataset
uspto-grants-2015_07
Patent number
US09090593B2

Reaction notes

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