Triethylamine → 5-(5-Bromo-3-pyridyl)-1H-tetrazole
Reaction equation
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([C:8]#[N:9])[CH:7]=1.[N-:10]=[N+:11]=[N-:12].[Na+].C(N(CC)CC)C>C(O)(=O)C>[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([C:8]2[N:10]=[N:11][NH:12][N:9]=2)[CH:7]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 3-bromo-5-cyanopyridine (1 eq), sodium azide (1.2 eq), triethylamine (1.2 eq) and AcOH (1.2 eq) was stirred at 100C for 14 h. The reaction mixture was cooled to rt, diluted with aqueous acetic acid solution and extracted with EtOAc. The organic extracts were washed with brine, dried over MgSO4, filtered and concentrated to afford the title compound.
Workup
- extractionextracted with EtOAc
- washThe organic extracts were washed with brine
- dry with materialdried over MgSO4
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-de2d78c4346d4d4881e3b60265e59a16
- Source dataset
- uspto-grants-2009_01
- Patent number
- US07482456B2
Reaction notes
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