2-Fluoropyridine → 1-(pyridin-2-yl)-1H-pyrrole-2-carbaldehyde

HRID 2427097Notes

Reaction equation

HRID 2427097 reaction equation
[NH:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]=[O:7].F[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CN1CCCC1=O>O>[N:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[N:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]=[O:7]

Participants

6

Reactant 4

HCID 97462-FluoropyridineHCID 10796Cesium carbonateHCID 13387N-methyl-2-pyrrolidoneHCID 13854Pyrrole-2-carboxaldehyde

Product 1

HCID 31574901-(pyridin-2-yl)-1H-pyrrole-2-carbaldehydeYield 43.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 10 g of 2-pyrrolecarbaldehyde, 10 g of 2-fluoropyridine, 24 g of cesium carbonate and 100 ml of N-methylpyrrolidone was stirred at 120° C. for 1 day. The reaction mixture was allowed to cool to room temperature. Water was poured into the 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 magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel chromatography to obtain 7.7 g of 1-(2-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 with water
  4. dry with materialan aqueous saturated sodium chloride solution, dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0d8f03100c2141fabc89f5bc1599e3c5
Source dataset
uspto-grants-2011_06
Patent number
US07968573B2

Reaction notes

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