Sodium Azide → 7-(Azidomethyl)[1,2,4]triazolo[1,5-a]pyridine

HRID 876826Notes

Reaction equation

HRID 876826 reaction equation
Cl[CH2:2][C:3]1[CH:8]=[CH:7][N:6]2[N:9]=[CH:10][N:11]=[C:5]2[CH:4]=1.[N-:12]=[N+:13]=[N-:14].[Na+]>CN(C=O)C>[N:12]([CH2:2][C:3]1[CH:8]=[CH:7][N:6]2[N:9]=[CH:10][N:11]=[C:5]2[CH:4]=1)=[N+:13]=[N-:14]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 67305720HCID 67305720, compound

Product 1

HCID 866714377-(Azidomethyl)[1,2,4]triazolo[1,5-a]pyridineYield 81.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 7-(chloromethyl)-[1,2,4]triazolo[1,5-a]pyridine (4-3) (400 mg, 2.4 mmol) in dried DMF (5 mL) was added NaN3 (250 mg, 3.6 mmol) under N2. The reaction mixture was stirred at 80° C. for 2 h, then quenched with aqueous Na2S2O3. The resulting mixture was extracted with EtOAc, dried on Na2SO4, and concentrated to afford the title compound (340 mg), which was used in next step without further purification. MS (m/z): 175 (M+1)+.

Workup

  1. customquenched with aqueous Na2S2O3
  2. extractionThe resulting mixture was extracted with EtOAc
  3. customdried on Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-727c1410f7244c2f8e28c4d7c307c80b
Source dataset
uspto-grants-2015_03
Patent number
US08987269B2

Reaction notes

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