反应详情

To a solution of 4-(trifluoromethyl)benzoic acid (115 mg, 605 μmol, CAS RN 328-90-5) in CH2Cl2 (2 mL) were added N-methyl-4-o-tolylpyridin-3-amine (0.1 g, 504 μmol, example 1, intermediate a), 2-bromo-1-ethylpyridinium tetrafluoroborate (166 mg, 605 μmol, CAS RN 878-23-9) and DIPEA (130 mg, 176 μL, 1.01 mmol). The reaction mixture was stirred at room temperature for 66 h. The red solution was poured on 10% aqueous citric acid and dichloromethane and the layers were separated. The aqueous layer was extracted twice with dichloromethane. The combined organic layers were washed with 10% aqueous citric acid solution and brine, dried over MgSO4, filtered, treated with silica gel and evaporated. The compound was purified by silica gel chromatography on a 20 g column using a MPLC system eluting with EtOAc (isocratic). The compound-containing fractions were evaporated and the residue was dissolved in dichloromethane and the solution washed twice with 2M aqueous Na2CO3 solution, twice with 1M aqueous HCl and once with brine, dried over MgSO4, filtered and evaporated. Brown solid (16%). MS (ESI): m/z=371.14 [M+H]+.

1. customthe layers were separated
2. extractionThe aqueous layer was extracted twice with dichloromethane
3. washThe combined organic layers were washed with 10% aqueous citric acid solution and brine
4. dry with materialdried over MgSO4
5. filtrationfiltered
6. additiontreated with silica gel
7. customevaporated
8. customThe compound was purified by silica gel chromatography on a 20 g column
9. washeluting with EtOAc (isocratic)
10. customThe compound-containing fractions were evaporated
11. dissolutionthe residue was dissolved in dichloromethane
12. washthe solution washed twice with 2M aqueous Na2CO3 solution, twice with 1M aqueous HCl and once with brine
13. dry with materialdried over MgSO4
14. filtrationfiltered
15. customevaporated