Sodium Azide → 5-Azidomethyl-2-fluoro-4-iodo-pyridine

HRID 561008Notes

Reaction equation

HRID 561008 reaction equation
Br[CH2:2][C:3]1[C:4]([I:10])=[CH:5][C:6]([F:9])=[N:7][CH:8]=1.[N-:11]=[N+:12]=[N-:13].[Na+]>CN(C)C=O.C(Cl)(Cl)Cl>[N:11]([CH2:2][C:3]1[C:4]([I:10])=[CH:5][C:6]([F:9])=[N:7][CH:8]=1)=[N+:12]=[N-:13]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 66674459HCID 66674459, compound

Product 1

HCID 866404905-Azidomethyl-2-fluoro-4-iodo-pyridineYield 82%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Procedure

Combine 5-bromomethyl-2-fluoro-4-iodo-pyridine (0.45 g, 1.4 mmol), sodium azide (370 mg, 5.7 mmol), and 18-crown ether (45 mg, 0.17 mml) in dimethylformamide (10 mL) in a round bottom flask. Stir the mixture for 4 hours at room temperature. Dilute the reaction mixture with chloroform, and wash with water and saturated aqueous sodium chloride. Separate the organic layer from the aqueous layer and dry over MgSO4. After filtration, evaporate the organic solvent in vacuo to give a crude product. Purify the crude with flash column chromatography (eluted with 20% methyl acetate in hexane) to give the title compound (colorless oil, 0.0.32 g, 82%). MS (ES) m/z 279 [M+1]+

Workup

  1. washwash with water and saturated aqueous sodium chloride
  2. customSeparate the organic layer from the aqueous layer
  3. dry with materialdry over MgSO4
  4. filtrationAfter filtration
  5. customevaporate the organic solvent in vacuo
  6. customto give a crude product
  7. customPurify the crude
  8. washwith flash column chromatography (eluted with 20% methyl acetate in hexane)

Sources & evidence

ORD record
ord-92ab2a9985944f2994d071ea3e6e62a5
Source dataset
uspto-grants-2011_11
Patent number
US08063212B2

Reaction notes

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