Triethylamine → 5-(5-Bromo-3-pyridyl)-1H-tetrazole

HRID 1455644Notes

Reaction equation

HRID 1455644 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]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 33557Sodium AzideHCID 7367935-Bromonicotinonitrile

Product 1

HCID 41737615-(5-Bromo-3-pyridyl)-1H-tetrazole

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

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

  1. extractionextracted with EtOAc
  2. washThe organic extracts were washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-de2d78c4346d4d4881e3b60265e59a16
Source dataset
uspto-grants-2009_01
Patent number
US07482456B2

Reaction notes

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