2-Fluoropyridine → HCID 10825211, compound

HRID 1647921Notes

Reaction equation

HRID 1647921 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[CH3:8][Sn:9](Cl)([CH3:11])[CH3:10]>C1COCC1>[F:1][C:2]1[C:7]([Sn:9]([CH3:11])([CH3:10])[CH3:8])=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 97462-FluoropyridineHCID 14016Trimethyltin chloride

Product 1

HCID 10825211HCID 10825211, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Metalation of 2-fluoropyridine was performed as described in Estel et al, J Org Chem (1988) 53:2740-2744. The lithium anion was quenched with 1 eq. of trimethyl tin chloride in THF (1 M) at -78° C. and stirred for 30', quenched with 1 M sodium bicarbonate and extracted with ethyl acetate. Upon Na2SO4 drying and evaporation under reduced pressure the resulting oil was used without further purification.

Workup

  1. customquenched with 1 M sodium bicarbonate
  2. extractionextracted with ethyl acetate
  3. customUpon Na2SO4 drying and evaporation under reduced pressure the resulting oil
  4. customwas used without further purification

Sources & evidence

ORD record
ord-a16e909f9b8d4ec598c0ceb9dc49d572
Source dataset
uspto-grants-1995_07
Patent number
US05434257

Reaction notes

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