Sodium Azide → 4-Azido-5-fluoropyridine-3-carbaldehyde

HRID 626717Notes

Reaction equation

HRID 626717 reaction equation
Cl[C:2]1[C:7]([F:8])=[CH:6][N:5]=[CH:4][C:3]=1[CH:9]=[O:10].[N-:11]=[N+:12]=[N-:13].[Na+]>CN(C=O)C>[N:11]([C:2]1[C:7]([F:8])=[CH:6][N:5]=[CH:4][C:3]=1[CH:9]=[O:10])=[N+:12]=[N-:13]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 717423064-Chloro-5-fluoropyridine-3-carbaldehyde

Product 1

HCID 866970534-Azido-5-fluoropyridine-3-carbaldehydeYield 84%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-chloro-5-fluoro-pyridine-3-carbaldehyde (4.15 g, 26.0 mmol) and sodium azide (1.86 g, 28.6 mmol) in DMF (15 mL) was stirred at room temperature for 18 hours. The reaction mixture was quenched with brine (200 mL) and extracted with ethyl acetate (3×75 mL). The combined organic extracts were dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel flash chromatography (0-50% ethyl acetate in cyclohexane) to afford the title compound as an off-white solid (3.61 g, 84% yield). 1H NMR (300 MHz, CDCl3): δ 10.32 (s, 1H), 8.79 (s, 1H), 8.58 (d, J=3.0 Hz, 1H).

Workup

  1. customThe reaction mixture was quenched with brine (200 mL)
  2. extractionextracted with ethyl acetate (3×75 mL)
  3. dry with materialThe combined organic extracts were dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel flash chromatography (0-50% ethyl acetate in cyclohexane)

Sources & evidence

ORD record
ord-e55fdf518d124993aabeb96dfa3d26cc
Source dataset
uspto-grants-2016_04
Patent number
US09309240B2

Reaction notes

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