反応 #40699

反応方程式

5-(trifloromethyl)-2(1H)-pyridone

4-iodoanisole

K2CO3

DMF

→

1-(4-methoxyphenyl)-5-(trifloromethyl)-2-pyridone

収率 39.2%

溶媒

ammonia

反応条件

後処理

1. 1
   抽出extracted with ethyl acetate
2. 2
   抽出The organic extract
3. 3
   洗浄was washed with saturated sodium chloride
4. 4
   乾燥dried over magnesium sulfate
5. 5
   その他evaporated
6. 6
   その他Column chromatography purification (30% ethyl acetate-hexane)

実験手順

A mixture of 5-(trifloromethyl)-2(1H)-pyridone (815.5 mg, 5 mmol), 4-iodoanisole (2.34 g, 10 mmol), CuI (952 mg, 5 mmol), K2CO3 (691 mg, 5 mmol) and DMF (5 ml) was heated at 135° C. overnight. The reaction mixture was diluted with 10% ammonia (15 ml) and extracted with ethyl acetate. The organic extract was washed with saturated sodium chloride, dried over magnesium sulfate and evaporated. Column chromatography purification (30% ethyl acetate-hexane) afforded 526 mg (39.2%) of 1-(4-methoxyphenyl)-5-(trifloromethyl)-2-pyridone. This compound (268.2 mg, 1 mmol) was treated with 1M BBr3 solution in dichloromethane (DCM, 2 ml) in DCM (5 ml) for 2 hours at 0° C. Reaction mixture was diluted with DCM and washed 3 times with water. Organic phase was dried over sodium sulfate and evaporated. The residue was separated by column chromatography (20% ethyl acetate-DCM) to afford the title compound as a off-white solid, 226 mg (89%). The 1H NMR spectra was consistent with the structure of Compound 10.

出典