반응 #1614475

반응 방정식

Triethylaluminum

5-bromo-1H-pyrazolo[3,4-c]pyridine

NH4Cl

→

5-Ethyl-1H-pyrazolo[3,4-c]pyridine

용매

THF

반응 조건

후처리

1. 1
   온도The mixture was cooled to RT
2. 2
   여과The resulting suspension was filtered
3. 3
   세척the solid was washed with water
4. 4
   추출were extracted with EtOAc (3×)
5. 5
   세척The combined organic extracts were washed with brine
6. 6
   기타dried (Phase separator)
7. 7
   농축concentrated under reduced pressure
8. 8
   기타The residual oil was purified by flash column chromatography on silica gel (EtOAc/c-hexane 50:50
9. 9
   기타0.71 min.

실험 절차

Triethylaluminum (21.7 mL, 40.4 mmol, 25 wt % solution in toluene) was added to a vigorously stirred solution of 5-bromo-1H-pyrazolo[3,4-c]pyridine [929617-35-6] (4.00 g, 20.2 mmol) and Pd(PPh3)4 (1.17 g, 1.01 mmol) in THF (100 mL) under argon. The reaction mixture was stirred at 65° C. for 60 h. The mixture was cooled to RT and poured into sat. aq. NH4Cl. The resulting suspension was filtered, the solid was washed with water and discarded. The filtrate and combined washings were extracted with EtOAc (3×). The combined organic extracts were washed with brine, then dried (Phase separator) and concentrated under reduced pressure. The residual oil was purified by flash column chromatography on silica gel (EtOAc/c-hexane 50:50, then 75:25, then 100:0). TLC, Rf (c-hexane/EtOAc 1:3)=0.22; MS (LC-MS): 148 [M+H]+, tR (HPLC conditions k): 0.71 min.

출처