Reacción #2000282

Ecuación de reacción

potassium iodide

sodium nitrite

8-(4-methoxyphenyl)-[1,2,4]-triazolo[1,5-a]pyridin-2-amine

p-toluenesulfonic acid

→

product

Rendimiento 65.4%

2-iodo-8-(4-methoxyphenyl)-[1,2,4]triazolo[1,5-a]pyridine

Rendimiento 65.4%

Disolventes

ethyl acetate

water

acetonitrile

Condiciones de reacción

Tratamiento posterior

1. 1
   Lavadothe resulting solution was washed sequentially with water (2×120 mL) and saturated aqueous sodium chloride solution (120 mL)
2. 2
   SecadoThe collected organic was dried over magnesium sulfate
3. 3
   Filtraciónfiltered
4. 4
   Concentraciónconcentrated in vacuo
5. 5
   OtroPurification by flash column chromatography (20→30% ethyl acetate in heptane)

Procedimiento

A solution of potassium iodide (5.4 g, 32 mmol, 3.9 equiv) and sodium nitrite (1.73 g, 25.1 mmol, 3.00 equiv) in water (10 mL) was added over 5 min to a solution of 8-(4-methoxyphenyl)-[1,2,4]-triazolo[1,5-a]pyridin-2-amine (2.01 g, 8.36 mmol, 1 equiv) and p-toluenesulfonic acid (7.3 g, 38 mmol, 4.6 equiv) in acetonitrile at 24° C. After 19 h, the reaction mixture was diluted with ethyl acetate (250 mL), and the resulting solution was washed sequentially with water (2×120 mL) and saturated aqueous sodium chloride solution (120 mL). The collected organic was dried over magnesium sulfate, filtered, and concentrated in vacuo. Purification by flash column chromatography (20→30% ethyl acetate in heptane) provided product as a light yellow solid (1.92 g, 65% yield). 1H NMR (400 MHz, CDCl3), δ: 8.46 (dd, J=6.8, 1.0 Hz, 1 H), 7.96 (m, 2 H), 7.59 (dd, J=7.4, 1.1 Hz, 1 H), 7.01-7.06 (m, 3 H), 3.86 (s, 3 H).

Fuente