Pyridine → tert-Butyl 5-bromo-1H-benzo[d][1,2,3]triazole-1-carboxylate

HRID 2307810Notes

Reaction equation

HRID 2307810 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]2[NH:6][N:7]=[N:8][C:4]=2[CH:3]=1.[C:11](Cl)(Cl)=[O:12].[CH3:15][C:16]([OH:19])([CH3:18])[CH3:17].N1C=CC=CC=1>C1COCC1.C1(C)C=CC=CC=1>[C:16]([O:19][C:11]([N:6]1[C:5]2[CH:9]=[CH:10][C:2]([Br:1])=[CH:3][C:4]=2[N:8]=[N:7]1)=[O:12])([CH3:18])([CH3:17])[CH3:15]

Participants

7

Reactant 4

HCID 1049PyridineHCID 6371PhosgeneHCID 6386tert-ButanolHCID 178419334HCID 178419334, compound

Product 1

HCID 69909976tert-Butyl 5-bromo-1H-benzo[d][1,2,3]triazole-1-carboxylateYield 76%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of Example 248B (770 mg; 5 mmol) in THF (5 mL) was added to a solution of 20% phosgene in toluene (10 mL) at −20° C., stirred for 1 hr. at −20° C. then 2 hrs. at r.t., evaporated and dissolved in THF (4 mL). This solution was added to a solution of tBuOH (1 mL), and pyridine (426 mg; 5.4 mmol) in THF (3 mL) at −20° C. then stirred overnight at r.t. The solids were removed by filtration and rinsed with EtOAc. The filtrate was rinsed with water and brine, dried (MgSO4), concentrated, and isolated by flash chromatography (1:1 Et2O:hexane) to provide the desired product (970 mg; 76%).

Workup

  1. customat −20° C.
  2. custom2 hrs
  3. customat r.t., evaporated
  4. dissolutiondissolved in THF (4 mL)
  5. stirringthen stirred overnight at r.t
  6. customThe solids were removed by filtration
  7. washrinsed with EtOAc
  8. washThe filtrate was rinsed with water and brine
  9. dry with materialdried (MgSO4)
  10. concentrationconcentrated
  11. customisolated by flash chromatography (1:1 Et2O:hexane)

Sources & evidence

ORD record
ord-1116250cfa20490fb817717ddb7ba6b0
Source dataset
uspto-grants-2004_12
Patent number
US06831175B2

Reaction notes

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