2-Fluoropyridine → HCID 10825211, compound

HRID 612794Notes

Reaction equation

HRID 612794 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, Marsais and Queguiner, J. Org. Chem. 53, 2740-2744, 1988. The lithium anion was quenched with 1 eq. of trimethyl tin chloride in THF (1M) at -78° C. and stirred for 30', quenched with 1M 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 1M 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-b85ef96c3a2645b8a31fc38a3993dde9
Source dataset
uspto-grants-1999_12
Patent number
US06005096

Reaction notes

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