3-[3-(6-Isopropylquinolin-8-yl)-phenyl]-2-[4-(methylsulfonyl)-phenyl]-prop-2-enenitrile → 3-[3-(6-Isopropyl-quinolin-8-yl)-phenyl]-2-(4-methanesulfonyl-phenyl)-propionitrile

HRID 896690Notes

Reaction equation

HRID 896690 reaction equation
[CH:1]([C:4]1[CH:5]=[C:6]2[C:11](=[C:12]([C:14]3[CH:15]=[C:16]([CH:20]=[C:21]([C:24]4[CH:29]=[CH:28][C:27]([S:30]([CH3:33])(=[O:32])=[O:31])=[CH:26][CH:25]=4)[C:22]#[N:23])[CH:17]=[CH:18][CH:19]=3)[CH:13]=1)[N:10]=[CH:9][CH:8]=[CH:7]2)([CH3:3])[CH3:2]>C1COCC1.CCO.[Pd]>[CH:1]([C:4]1[CH:5]=[C:6]2[C:11](=[C:12]([C:14]3[CH:15]=[C:16]([CH2:20][CH:21]([C:24]4[CH:25]=[CH:26][C:27]([S:30]([CH3:33])(=[O:32])=[O:31])=[CH:28][CH:29]=4)[C:22]#[N:23])[CH:17]=[CH:18][CH:19]=3)[CH:13]=1)[N:10]=[CH:9][CH:8]=[CH:7]2)([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 696943163-[3-(6-Isopropylquinolin-8-yl)-phenyl]-2-[4-(methylsulfonyl)-phenyl]-prop-2-enenitrile

Product 1

HCID 102045083-[3-(6-Isopropyl-quinolin-8-yl)-phenyl]-2-(4-methanesulfonyl-phenyl)-propionitrile

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

A solution of the nitrile from Step 2 (400 mg, 0.88 mmol) in THF/EtOH (1:1, 10 mL) containing Pd/C (10%, 40 mg) was stirred under H2 (1 atm) for 3 days. Filtration on celite, evaporation, stirring vigorously in ether for 1 h then filtration afforded the 3-[3-(6-Isopropyl-quinolin-8-yl)-phenyl]-2-(4-methanesulfonyl-phenyl)-propionitrile compound as a white powder.

Workup

  1. filtrationFiltration
  2. customon celite, evaporation
  3. stirringstirring vigorously in ether for 1 h
  4. filtrationfiltration

Sources & evidence

ORD record
ord-5816ba1c4f354c48bccf7d2f0a5f48b1
Source dataset
uspto-grants-2005_07
Patent number
US06919353B2

Reaction notes

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