Triethylsilane → 4-(trifluoromethyl)quinoline

HRID 513733Notes

Reaction equation

HRID 513733 reaction equation
C([SiH](CC)CC)C.Cl[C:9]1[CH:18]=[C:17]([C:19]([F:22])([F:21])[F:20])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]=1>CC#N>[F:22][C:19]([F:20])([F:21])[C:17]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]=[CH:9][CH:18]=1

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 27829122-Chloro-4-(trifluoromethyl)quinoline

Product 1

HCID 27778074-(trifluoromethyl)quinolineYield 47%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

Pd (PPh3)2Cl2 (170 mg, 0.24 mmol) and triethylsilane (5.4 ml, 33.9 mmol) were added to a solution of 2-chloro-4-trifluoromethyl-quinoline 466 (5.60 g, 24.2 mmol) in MeCN (3 ml) and the mixture was heated at 70° C. for 18 h. The solvent was removed in vacuo. The crude residue was purified by column chromatography with n-hexane/EtOAc (95:5) to give the title compound (2.2 g, 47%).

Workup

  1. customThe solvent was removed in vacuo
  2. customThe crude residue was purified by column chromatography with n-hexane/EtOAc (95:5)

Sources & evidence

ORD record
ord-06a641d17a804ebc8f87a5b8621af87f
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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