Cesium carbonate → 1-(3,5-dichloro-4-pyridinyl)-1H-pyrrole-2-carbaldehyde

HRID 2427086Notes

Reaction equation

HRID 2427086 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:9])[C:7]=1Cl.[C:10](=[O:13])([O-])[O-].[Cs+].[Cs+].C[N:17]1[CH2:21][CH2:20][CH2:19][C:18]1=O>O>[Cl:9][C:6]1[CH:5]=[N:4][CH:3]=[C:2]([Cl:1])[C:7]=1[N:17]1[CH:21]=[CH:20][CH:19]=[C:18]1[CH:10]=[O:13]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 13387N-methyl-2-pyrrolidoneHCID 37865313,4,5-Trichloropyridine

Product 1

HCID 866325531-(3,5-dichloro-4-pyridinyl)-1H-pyrrole-2-carbaldehyde

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2.6 g of 2-pyrrolecabaldehyde, 5.0 g of 3,4,5-trichloropyridine, 10.7 g of cesium carbonate and 30 ml of N-methylpyrrolidone was stirred at 100° C. for 2 hours, and then allowed to cool to room temperature. Water was poured into the reaction mixture, and the mixture was extracted with ethyl acetate two times. The organic layers were combined, washed successively 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 2.14 g of 1-(3,5-dichloro-4-pyridinyl)-1H-pyrrole-2-carbaldehyde of the formula:

Workup

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

Sources & evidence

ORD record
ord-dddc57e0c3aa4c62932c7c58ef723736
Source dataset
uspto-grants-2011_06
Patent number
US07968573B2

Reaction notes

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