Water → HCID 86632551, compound

HRID 251970Notes

Reaction equation

HRID 251970 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[N:3][C:2]=1[N:7]1[CH:11]=[CH:10][CH:9]=[C:8]1[CH:12]=[O:13].[Br:14]N1C(=O)CCC1=O.O>CN(C)C=O>[Br:14][C:11]1[N:7]([C:2]2[N:3]=[CH:4][CH:5]=[CH:6][N:1]=2)[C:8]([CH:12]=[O:13])=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 37988701-pyrimidin-2-yl-1H-pyrrole-2-carbaldehyde

Product 1

HCID 86632551HCID 86632551, compoundYield 59.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 0.5 g of 1-(2-pyrimidinyl)-1H-pyrrole-2-carbaldehyde in 10 ml of N,N-dimethylformamide was added 0.6 g of N-bromosuccinimide. The resulting mixture was stirred at room temperature for 1 hour. Water was poured into the reaction mixture, and the mixture was extracted with ethyl acetate two times. The organic layers were combined, washed successively with water and an aqueous saturated sodium chloride solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel chromatography to obtain 0.43 g of 5-bromo-1-(2-pyrimidinyl)-1H-pyrrole-2-carbaldehyde of the formula:

Workup

  1. extractionthe mixture was extracted with ethyl acetate two times
  2. washwashed successively with water
  3. dry with materialan aqueous saturated sodium chloride solution, dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-70de0a73613a4a5ca2826aca67b732e3
Source dataset
uspto-grants-2011_01
Patent number
US07867949B2

Reaction notes

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