Sodium Hydroxide → 5-Chloro-8-iodo[1,2,4]triazolo[1,5-a]pyridine

HRID 1011244Notes

Reaction equation

HRID 1011244 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH:8]/[CH:9]=[N:10]/O)[C:5]([I:12])=[CH:4][CH:3]=1.[OH-].[Na+]>O>[Cl:1][C:2]1[N:7]2[N:10]=[CH:9][N:8]=[C:6]2[C:5]([I:12])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178526380HCID 178526380, compound

Product 1

HCID 576643495-Chloro-8-iodo[1,2,4]triazolo[1,5-a]pyridineYield 100.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

(E)-N-(6-chloro-3-iodopyridin-2-yl)-N′-hydroxyformimidamide (6.0 g, 0.02 mol) is treated with polyphosphoric acid (40 g) at 80° C. for 4 h with stirring. The reaction mixture is diluted with cold water (100 mL), and then neutralized with 10 N aq. sodium hydroxide solution to pH 8. The aqueous solution is extracted with dichloromethane (100 mL×3). The combined organic extracts are washed with saturated aq. sodium bicarbonate solution (50 mL), brine (30 mL×3), dried over sodium sulfate, filtered, and filtrate concentrated to afford 5-Chloro-8-iodo-[1,2,4]triazolo[1,5-a]pyridine (5.6 g, 94%) as an off-white solid. LCMS Purity: 95% by UV 254 nm detection; LCMS-ESI (m/z): calcd for C6H3ClIN3, 278.9; [M+H]+ found, 279.9. 1H NMR (300 MHz, DMSO-d6) δ 8.63 (s, 1H), 8.15 (d, J=7.8 Hz, 1H), 7.29 (d, J=7.8 Hz, 1H).

Workup

  1. extractionThe aqueous solution is extracted with dichloromethane (100 mL×3)
  2. washThe combined organic extracts are washed with saturated aq. sodium bicarbonate solution (50 mL), brine (30 mL×3)
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationfiltrate concentrated

Sources & evidence

ORD record
ord-61106e04004a46a3ba4155a2f7128455
Source dataset
uspto-grants-2011_07
Patent number
US07977352B2

Reaction notes

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