2-Aminopyridine → HCID 18008032, compound

HRID 988221Notes

Reaction equation

HRID 988221 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.Br[CH:9]([CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:10](OCC)=[O:11].[Na].[F:23][C:24]1[CH:31]=[CH:30][C:27]([CH2:28]Br)=[CH:26][CH:25]=1>CCOCC.C(O)C>[CH2:15]([C:9]1([CH2:28][C:27]2[CH:30]=[CH:31][C:24]([F:23])=[CH:25][CH:26]=2)[N:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]2=[N:1][C:10]1=[O:11])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

7

Reactant 4

HCID 104392-AminopyridineHCID 680214-Fluorobenzyl bromideHCID 4737529Ethyl 2-bromo-3-phenylpropanoateHCID 5360545Sodium

Product 1

HCID 18008032HCID 18008032, compoundYield 1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

630 mg (6.7 mmol) of 2-aminopyridine and 1.72 g (6.7 mmol) of ethyl 2-bromo-3-phenylpropionate were refluxed under heating in 50 ml of ether for 12 hours. The reaction mixture was allowed to cool to room temperature and ether was removed by decantation. The residue was added with and dissolved in 30 ml of absolute ethanol, which was added to a solution of 150 mg (6.5 mmol) of sodium in 10 ml of absolute ethanol and stirred at room temperature for one hour. Then, 0.8 ml (6.5 mmol) of 4-fluorobenzylbromide was added and stirred for overnight. The reaction mixture was added to ice water and extracted with methylene chloride. Then, the solvent was removed under reduced pressure and the residue was purified with silica gel column chromatography, thus obtaining 22 mg (yield: 1%) of the titled compound.

Workup

  1. customether was removed by decantation
  2. additionThe residue was added with and
  3. dissolutiondissolved in 30 ml of absolute ethanol
  4. stirringstirred for overnight
  5. extractionextracted with methylene chloride
  6. customThen, the solvent was removed under reduced pressure
  7. customthe residue was purified with silica gel column chromatography

Sources & evidence

ORD record
ord-341b7fbd82a845f494565c5adfd8bd14
Source dataset
uspto-grants-2003_10
Patent number
US06635652B1

Reaction notes

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