反应详情

温度

120 °C

A mixture of N-{4-[2-chloro-6-(4-trifluoromethyl-phenyl)-pyrimidin-4-yloxy]-benzothiazol-2-yl}-acetamide (300 mg, 0.645 mmol, Example 7(d)), tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate (216 mg, 0.70 mmol, Aldrich), Pd(OAc)2 (7.2 mg, 0.03 mmol, Aldrich), PPh3 (17 mg, 0.065 mmol) and 2N aqueous Na2CO3 (0.65 mL) in 1,2-dimethoxyethane (3.0 mL) was heated at 120° C. in a microwave synthesizer for 25 min. The reaction mixture was cooled to room temperature, diluted with saturated aqueous solution of NaHCO3 (10 mL) and extracted with EtOAc (2×50) mL. The combined EtOAc extracts were dried over Na2SO4, filtered, and concentrated in vacuo. The yellow solid residue was dissolved in DCM (4 mL) and treated with trifluoroacetic acid (1 mL). The mixture was stirred at room temperature for 1.5 h and the volatiles were evaporated in vacuo. The residue was partitioned between 1N HCl (5 mL) and Et2O (5 mL). The aqueous layer was separated, basified with 2N NaOH, and extracted with EtOAc (3×15 mL). The combined EtOAc extracts were dried over Na2SO4, filtered, and concentrated in vacuo. Purification of the residue by silica gel column chromatography (gradient 1-25% (2N NH3 in MeOH)/EtOAc) afforded the title compound as an off-white solid. MS (ESI, pos. ion.) m/z: 512 (M+1).

1. temperatureThe reaction mixture was cooled to room temperature
2. extractionextracted with EtOAc (2×50) mL
3. dry with materialThe combined EtOAc extracts were dried over Na2SO4
4. filtrationfiltered
5. concentrationconcentrated in vacuo
6. dissolutionThe yellow solid residue was dissolved in DCM (4 mL)
7. additiontreated with trifluoroacetic acid (1 mL)
8. customthe volatiles were evaporated in vacuo
9. customThe residue was partitioned between 1N HCl (5 mL) and Et2O (5 mL)
10. customThe aqueous layer was separated
11. extractionextracted with EtOAc (3×15 mL)
12. dry with materialThe combined EtOAc extracts were dried over Na2SO4
13. filtrationfiltered
14. concentrationconcentrated in vacuo
15. customPurification of the residue by silica gel column chromatography (gradient 1-25% (2N NH3 in MeOH)/EtOAc)