反応 #87561

反応方程式

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

収率 54.1%

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

収率 54.1%

溶媒

acetonitrile

反応条件

後処理

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

実験手順

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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