Triethylsilane → 4-(Trifluoromethyl)quinoline
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]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
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
- customThe solvent was removed in vacuo
- 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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