반응 #44002

반응 방정식

Compound 52

6-phenyl-1,4,6,7-tetrahydro-pyrazolo[4,3-c]pyridine-5-carboxylic acid tert-butyl ester

4-chlorophenylsulfonyl chloride

→

1,5-bis-(4-chloro-benzenesulfonyl)-6-phenyl-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridine

용매

Ethyl acetate

ethyl acetate

반응 조건

후처리

1. 1
   기타HCl (g) was bubbled into the solution for 5 minutes
2. 2
   기타Solvent was removed under reduced pressure
3. 3
   workup.DISSOLUTIONthe residue was re-dissolved in pyridine (15 ml)
4. 4
   workup.STIRRINGupon stirring overnight
5. 5
   세척the solution was washed with sat. NaHCO3 (2×25 ml), 10% HCl solution (2×25 ml) and brine (10 ml)
6. 6
   건조Sample dried over (MgSO4), and solvent
7. 7
   기타was removed under reduced pressure
8. 8
   기타The crude product was purified via flash chromatography
9. 9
   세척eluted with EtOAc/hexane (15:85)
10. 10
    기타to give a white solid
11. 11
    workup.ADDITIONas the mixture of two regioisomers

실험 절차

Compound 52 from the previous step (1.1 g, 3.67 mmol) was dissolved in ethyl acetate (15 ml). HCl (g) was bubbled into the solution for 5 minutes. Solvent was removed under reduced pressure and the residue was re-dissolved in pyridine (15 ml). 4-chlorophenylsulfonyl chloride (1.55 g, 2.2 eq.) was added to the solution at zero degrees. The mixture was stirred at zero degrees and slowly raised to room temperature upon stirring overnight. Ethyl acetate (100 ml) was added to the reaction mixture, and the solution was washed with sat. NaHCO3 (2×25 ml), 10% HCl solution (2×25 ml) and brine (10 ml). Sample dried over (MgSO4), and solvent was removed under reduced pressure. The crude product was purified via flash chromatography, eluted with EtOAc/hexane (15:85) to give a white solid as the mixture of two regioisomers. LCMS 569.9 (M+23)

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