반응 #470406

반응 방정식

2-hydroxypyridine

K2CO3

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

oxalyl chloride

→

title product

수율 46.0%

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

수율 46.0%

용매

dichloromethane

dichloromethane

반응 조건

후처리

1. 1
   기타prepared
2. 2
   기타at room temperature
3. 3
   농축concentrated under vacuum
4. 4
   workup.DISSOLUTIONThe residue was dissolved in dichloromethane (10 mL)
5. 5
   기타The resulting reaction mixture
6. 6
   workup.STIRRINGwas stirred at room temperature overnight
7. 7
   여과The reaction mixture was filtered through a short pad of Celite® diatomaceous filter aid
8. 8
   세척the pad was rinsed with dichloromethane
9. 9
   농축The combined filtrate was concentrated
10. 10
    기타the residue was purified by column chromatography on silica gel

실험 절차

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).

출처