Sodium Azide → 5-Azido-1,6-naphthyridine

HRID 1772017Notes

Reaction equation

HRID 1772017 reaction equation
Cl[C:2]1[N:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.[N-:12]=[N+:13]=[N-:14].[Na+]>CN(C=O)C>[N:12]([C:2]1[N:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2)=[N+:13]=[N-:14]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 122042345-Chloro-1,6-naphthyridine

Product 1

HCID 866678085-Azido-1,6-naphthyridineYield 96%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 5-chloro-1,6-naphthyridine (500 mg, 3.04 mmol) in DMF (5 mL) was stirred at room temperature. Sodium azide (592 mg, 9.12 mmol) was added to the mixture, and the mixture was stirred at 80° C. for 4 h. The mixture was cooled to room temperature and filtered through Celite to remove a white solid. The filtrate was diluted with EtOAc (25 mL) and washed with brine (5×5 mL). The combined organic layers were dried with Na2SO4, filtered, and the solvent was removed under reduced pressure to yield 5-azido-1,6-naphthyridine as a yellow solid, which was used in the next step without further purification (500 mg, yield 96%). ESI MS: m/z 172 [M+H]+.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. filtrationfiltered through Celite
  3. customto remove a white solid
  4. additionThe filtrate was diluted with EtOAc (25 mL)
  5. washwashed with brine (5×5 mL)
  6. dry with materialThe combined organic layers were dried with Na2SO4
  7. filtrationfiltered
  8. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-3ee252c0aa3f4f65bec25f4db2fe0225
Source dataset
uspto-grants-2016_02
Patent number
US09249162B2

Reaction notes

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