反应 #87561

反应方程式

potassium iodide

sodium nitrite

1-(4-amino-3-methoxyphenyl)-3-(2-chloro-6-fluorophenyl)-1H-1,2,4-triazol-5(4H)-one

PTSA

→

desired product

收率 54.1%

3-(2-chloro-6-fluorophenyl)-1-(4-iodo-3-methoxyphenyl)-1H-1,2,4-triazol-5(4H)-one

收率 54.1%

溶剂

acetonitrile

反应条件

后处理

1. 1
   workup.STIRRINGfurther stirred for 2 h
2. 2
   其他Excess solvent was removed under vacuum
3. 3
   其他the residue reaction mass
4. 4
   其他was quenched in water
5. 5
   萃取extracted with ethyl acetate
6. 6
   洗涤The organic layer was washed with sodium metabisulphate
7. 7
   浓缩concentrated
8. 8
   其他to obtain a crude product, which
9. 9
   其他was further purified by column chromatography on silica gel eluting with 10% EtOAc

实验过程

To a solution of 1-(4-amino-3-methoxyphenyl)-3-(2-chloro-6-fluorophenyl)-1H-1,2,4-triazol-5(4H)-one (0.280 g, 0.83 mmol) in acetonitrile (5.0 ml) was added PTSA (0.477 g, 2.51 mmol). The reaction mass was stirred at RT for 1 h followed by addition of potassium iodide (0.347 g, 2.0 mmol) and sodium nitrite (0.115 g, 1.67 mmol) at 0-5° C. and further stirred for 2 h. Excess solvent was removed under vacuum and the residue reaction mass was quenched in water and extracted with ethyl acetate. The organic layer was washed with sodium metabisulphate and concentrated to obtain a crude product, which was further purified by column chromatography on silica gel eluting with 10% EtOAc: pet. ether to afford 0.200 g of desired product. 1H NMR (300 MHz, DMSO d6): δ 3.85 (s, 3H), 7.40 (d, J=8.7 Hz, 1H), 7.46-7.74 (m, 4H), 7.83 (d, J=8.1 Hz, 1H), 12.71 (br s, 1H); MS (m/z): 445.84 (M+H)+.

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