Reaction #470406
ord-c35ce055db994dbca3abd04216ff14cc
Reaction equation
Reactants
Reagents
Solvents
Conditions
Workup
- 1Otherprepared
- 2Otherat room temperature
- 3Concentrationconcentrated under vacuum
- 4workup.DISSOLUTIONThe residue was dissolved in dichloromethane (10 mL)
- 5OtherThe resulting reaction mixture
- 6workup.STIRRINGwas stirred at room temperature overnight
- 7FiltrationThe reaction mixture was filtered through a short pad of Celite® diatomaceous filter aid
- 8Washthe pad was rinsed with dichloromethane
- 9ConcentrationThe combined filtrate was concentrated
- 10Otherthe residue was purified by column chromatography on silica gel
Procedure
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).