反応 #470406

反応方程式

2-hydroxypyridine

K2CO3

4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-1-naphthalenecarboxylic acid

oxalyl chloride

→

title product

収率 46.0%

2-pyridinyl 4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-1-naphthalenecarboxylate

収率 46.0%

溶媒

dichloromethane

dichloromethane

反応条件

後処理

1. 1
   その他prepared
2. 2
   その他at room temperature
3. 3
   濃縮concentrated under vacuum
4. 4
   workup.DISSOLUTIONThe residue was dissolved in dichloromethane (10 mL)
5. 5
   その他The resulting reaction mixture
6. 6
   workup.STIRRINGwas stirred at room temperature overnight
7. 7
   ろ過The reaction mixture was filtered through a short pad of Celite® diatomaceous filter aid
8. 8
   洗浄the pad was rinsed with dichloromethane
9. 9
   濃縮The combined filtrate was concentrated
10. 10
    その他the residue was purified by column chromatography on silica gel

実験手順

To a stirred suspension of 4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-1-naphthalenecarboxylic acid (prepared according to the procedure described in WO 2007/079162, 1.50 g, 3.30 mmol) in dichloromethane (15 mL) at room temperature was added oxalyl chloride (0.58 mL, 6.60 mmol) followed by one drop of N,N-dimethylformamide. The reaction mixture was stirred at room temperature for 2 h and then concentrated under vacuum. The residue was dissolved in dichloromethane (10 mL) and added to a stirred suspension of 2-hydroxypyridine (0.38 g, 3.96 mmol) and K2CO3 (1.37 g, 9.90 mmol) in dichloromethane (15 mL) at room temperature. The resulting reaction mixture was stirred at room temperature overnight. The reaction mixture was filtered through a short pad of Celite® diatomaceous filter aid, and the pad was rinsed with dichloromethane. The combined filtrate was concentrated and the residue was purified by column chromatography on silica gel using hexane/EtOAc as eluent to provide the title product as a yellow solid (0.80 g, 46% yield).

出典