Water → 2-(2-bromo-1H-pyrrol-1-yl)-3-chloropyridine

HRID 251968Notes

Reaction equation

HRID 251968 reaction equation
[Cl:1][C:2]1[C:3]([N:8]2[CH:12]=[CH:11][CH:10]=[CH:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1.[Br:13]N1C(=O)CCC1=O.O>CN(C)C=O>[Br:13][C:9]1[N:8]([C:3]2[C:2]([Cl:1])=[CH:7][CH:6]=[CH:5][N:4]=2)[CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 587620843-chloro-2-(1H-pyrrol-1-yl)pyridine

Product 1

HCID 668542432-(2-bromo-1H-pyrrol-1-yl)-3-chloropyridineYield 25.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3.0 g of 3-chloro-2-(1H-pyrrol-1-yl)pyridine in 30 ml of N,N-dimethylformamide was added 3.1 g of N-bromosuccinimide. The resulting mixture was stirred at room temperature for 6 hours. Water was poured into the reaction mixture, and the mixture was extracted with ethyl acetate two times. The organic layers were combined, washed with an aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 1.1 g of 2-(2-bromo-1H-pyrrol-1-yl)-3-chloropyridine of the formula:

Workup

  1. extractionthe mixture was extracted with ethyl acetate two times
  2. washwashed with an aqueous saturated sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0a22250d4e4747ab903b9d4f2e7c378e
Source dataset
uspto-grants-2011_01
Patent number
US07867949B2

Reaction notes

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