反応 #61553

反応方程式

4-Iodo-1H-pyrazole-3,5-dicarboxylic acid diethyl ester

1,10-Phenanthroline

2,2,2-trifluoro-ethanol

HCl

→

4-(2,2,2-Trifluoro-ethoxy)-1H-pyrazole-3,5-dicarboxylic acid diethyl ester

溶媒

ethanol

反応条件

後処理

1. 1
   温度The reaction mixture heated for 4 h to 100° C. under microwave irradiation (100 W, CEM Discover™ apparatus)
2. 2
   その他After 16 h the solvents were removed under reduced pressure
3. 3
   その他The organic phase was separated
4. 4
   抽出the aqueous layer was extracted with DCM (2×50 ml)
5. 5
   乾燥The combined organic layers were dried over MgSO4
6. 6
   ろ過filtered
7. 7
   その他the solvent was removed under reduced pressure
8. 8
   その他The residue was purified by preparative HPLC (
9. 9
   洗浄C18 reverse phase column, elution with a H2O/MeCN gradient with 0.1% TFA)
10. 10
    workup.ADDITIONThe fractions containing the product
11. 11
    その他were evaporated
12. 12
    その他to yield a white solid

実験手順

To a solution of 1 g 4-Iodo-1H-pyrazole-3,5-dicarboxylic acid diethyl ester in 5 ml 2,2,2-trifluoro-ethanol 1.4 g Cs2CO3, 56 mg CuI and 106 mg 1,10-Phenanthroline were added. The reaction mixture heated for 4 h to 100° C. under microwave irradiation (100 W, CEM Discover™ apparatus). Then 10 HCl in ethanol (8M) was added and the solution was stirred at RT. After 16 h the solvents were removed under reduced pressure and the residue taken up in DCM and water. The organic phase was separated and the aqueous layer was extracted with DCM (2×50 ml). The combined organic layers were dried over MgSO4, filtered and the solvent was removed under reduced pressure. The residue was purified by preparative HPLC (C18 reverse phase column, elution with a H2O/MeCN gradient with 0.1% TFA). The fractions containing the product were evaporated and lyophilized to yield a white solid. Yield: 359 mg.

出典