Iodobenzene diacetate → 5-Bromo-3-methyl-[1,2,3]triazolo[1,5-a]pyridine

HRID 879576Notes

Reaction equation

HRID 879576 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4](/[C:8](=[N:10]\[NH2:11])/[CH3:9])[CH:3]=1.C(OI(C1C=CC=CC=1)OC(=O)C)(=O)C>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][N:5]2[N:11]=[N:10][C:8]([CH3:9])=[C:4]2[CH:3]=1

Participants

4

Reactant 2

HCID 76724Iodobenzene diacetateHCID 898605244-Bromo-2-[(1Z)-1-hydrazinylideneethyl]pyridine

Product 1

HCID 826605365-Bromo-3-methyl-[1,2,3]triazolo[1,5-a]pyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirring solution of (Z)-4-bromo-2-(1-hydrazonoethyl)pyridine (2.53 g, 11.8 mmol) in DCM (40 mL) was added (diacetoxyiodo)benzene (3.8 g, 11.8 mmol) in small portions over several minutes and stirred at room temperature for 45 minutes. The reaction was quenched with saturated 1:1 Na2S2O3/NaHCO3 solution (40 mL) and stirred until gas evolution ceased. The aqueous layer was extracted with DCM, dried over MgSO4, and purified by column chromatography (gradient 0 to 45% EtOAc in hexanes) to afford the product. 1H NMR (400 MHz, CDCl3) δ 8.50 (d, J=6.9 Hz, 2H), 7.79 (s, 2H), 6.97 (d, J=6.5 Hz, 2H), 2.57 (s, 7H).

Workup

  1. customThe reaction was quenched with saturated 1:1 Na2S2O3/NaHCO3 solution (40 mL)
  2. stirringstirred until gas evolution
  3. extractionThe aqueous layer was extracted with DCM
  4. dry with materialdried over MgSO4
  5. custompurified by column chromatography (gradient 0 to 45% EtOAc in hexanes)
  6. customto afford the product

Sources & evidence

ORD record
ord-8369f3ad1bf2457dbd5f44644071ba52
Source dataset
uspto-grants-2015_03
Patent number
US08987250B2

Reaction notes

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