Potassium Iodide → 2-Iodo-5-(4-methoxyphenyl)-[1,2,4]triazolo[1,5-a]pyridine

HRID 336400Notes

Reaction equation

HRID 336400 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:14]3[N:15]=[C:16](N)[N:17]=[C:13]3[CH:12]=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.[I-:30].[K+].N([O-])=O.[Na+]>C(#N)C.O.C(OCC)(=O)C>[I:30][C:16]1[N:17]=[C:13]2[CH:12]=[CH:11][CH:10]=[C:9]([C:6]3[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)[N:14]2[N:15]=1

Participants

8

Reactant 4

HCID 4875Potassium IodideHCID 6101p-Toluenesulfonic acidHCID 23668193Sodium NitriteHCID 591864185-(4-Methoxyphenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine

Product 1

HCID 591862192-Iodo-5-(4-methoxyphenyl)-[1,2,4]triazolo[1,5-a]pyridineYield 78.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-(4-methoxyphenyl)[1,2,4]triazolo[1,5-a]pyridin-2-amine (825 mg, 3.43 mmol) and p-toluene sulphonic acid (1.77 g, 10.3 mmol) in acetonitrile (40 mL) was added a solution of potassium iodide (1.42 g, 8.55 mmol) and sodium nitrite (474 mg, 6.87 mmol) in water (2 mL) at 24° C. After 18 h, ethyl acetate was added to the reaction mixture. The resulting solution was washed with water (2×) and saturated aqueous sodium chloride solution. The organic was dried over magnesium sulfate, filtered, and concentrated. Purification using ISCO CombiFlash (2→5% methanol in dichloromethane) afforded 2-iodo-5-(4-methoxyphenyl)-[1,2,4]triazolo[1,5-a]pyridine (950 mg, 71%). 1H NMR (400 MHz, CDCl3), δ: 7.90 (d, 2H), 7.64 (m, 1H), 7.57 (t, 1H), 7.05 (t, 3H); ES-MS m/z 351.9.

Workup

  1. washThe resulting solution was washed with water (2×) and saturated aqueous sodium chloride solution
  2. dry with materialThe organic was dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification

Sources & evidence

ORD record
ord-9ccf36d6593f4f4592d80f57ec50e2ed
Source dataset
uspto-grants-2014_11
Patent number
US08889673B2

Reaction notes

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