Réaction #470406

Équation de réaction

2-hydroxypyridine

K2CO3

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

oxalyl chloride

→

title product

Rendement 46.0%

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

Rendement 46.0%

Solvants

dichloromethane

dichloromethane

Conditions de réaction

Traitement

1. 1
   Autreprepared
2. 2
   Autreat room temperature
3. 3
   Concentrationconcentrated under vacuum
4. 4
   workup.DISSOLUTIONThe residue was dissolved in dichloromethane (10 mL)
5. 5
   AutreThe resulting reaction mixture
6. 6
   workup.STIRRINGwas stirred at room temperature overnight
7. 7
   FiltrationThe reaction mixture was filtered through a short pad of Celite® diatomaceous filter aid
8. 8
   Lavagethe pad was rinsed with dichloromethane
9. 9
   ConcentrationThe combined filtrate was concentrated
10. 10
    Autrethe residue was purified by column chromatography on silica gel

Mode opératoire

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).

Source