Sodium Azide → 7-(Azidomethyl)-[1,2,4]triazolo[1,5-a]pyridine
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
Product 1
Reagents, catalysts & solvents 1
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
- customquenched with aqueous Na2S2O3
- extractionThe resulting mixture was extracted with EtOAc
- customdried on Na2SO4
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-727c1410f7244c2f8e28c4d7c307c80b
- Source dataset
- uspto-grants-2015_03
- Patent number
- US08987269B2
Reaction notes
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