2-Fluoropyridine → HCID 10825211, compound

HRID 1167393Notes

Reaction equation

HRID 1167393 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 (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-1f06c4f98c6d44648b9af40949130aea
Source dataset
uspto-grants-2003_09
Patent number
US06617437B1

Reaction notes

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