反应详情

温度

150 °C

N-(2-adamantyl)-1-(4-chloro-2-methyl-phenyl)-5-tert-butyl-pyrazole-4-carboxamide (Intermediate#114) (647 mg, 1.52 mmol), Molybdenum hexacarbonyl (0.102 mL, 0.76 mmol), 4-Dimethylaminopyridine (371 mg, 3.04 mmol), N-Ethyldiisopropylamine (0.529 mL, 3.04 mmol), trans-Di-mu-acetatobis[2-(di-o-tolylphosphino)benzyl]dipalladium(II) (71.4 mg, 0.08 mmol) and Tri-tert-butylphosphine tetrafluoroborate (88 mg, 0.30 mmol) were suspended in ethanol (6 mL) and dioxane (6.00 mL) and sealed into a microwave tube. The reaction was heated to 150° C. for 1 hour in the microwave reactor and cooled to RT. The reaction mixture was evaporated to dryness and redissolved in EtOAc (100), and washed with water (10 mL), filtered, then washed with 2M HCl (10 mL), and saturated brine (10 mL). The organic layer was dried over MgSO4, filtered and evaporated to afford crude product. The crude product was purified by flash silica chromatography, elution gradient 0 to 25% EtOAc in isohexane. Pure fractions were evaporated to dryness to afford ethyl 4-[4-(2-adamantylcarbamoyl)-5-tert-butyl-pyrazol-1-yl]-3-methyl-benzoate (352 mg, 50.0%) as a colourless oil.

1. temperaturecooled to RT
2. customThe reaction mixture was evaporated to dryness
3. dissolutionredissolved in EtOAc (100)
4. washwashed with water (10 mL)
5. filtrationfiltered
6. washwashed with 2M HCl (10 mL), and saturated brine (10 mL)
7. dry with materialThe organic layer was dried over MgSO4
8. filtrationfiltered
9. customevaporated
10. customto afford crude product
11. customThe crude product was purified by flash silica chromatography, elution gradient 0 to 25% EtOAc in isohexane
12. customPure fractions were evaporated to dryness