Ethyl acetate hexane → 4-Methyl-2-(2-methylprop-1-enyl)-7-(trifluoromethyl)quinoline-3-carboxylic acid ethyl ester
Reaction equation
[CH3:1][C:2]([CH3:6])=[CH:3][Mg]Br.[CH2:7]([O:9][C:10]([C:12]1[C:13](OS(C(F)(F)F)(=O)=O)=[N:14][C:15]2[C:20]([C:21]=1[CH3:22])=[CH:19][CH:18]=[C:17]([C:23]([F:26])([F:25])[F:24])[CH:16]=2)=[O:11])[CH3:8].CCOC(C)=O.CCCCCC>C1COCC1.Cl[Ni]1(Cl)[P](C2C=CC=CC=2)(C2C=CC=CC=2)CCC[P]1(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:7]([O:9][C:10]([C:12]1[C:13]([CH:1]=[C:2]([CH3:6])[CH3:3])=[N:14][C:15]2[C:20]([C:21]=1[CH3:22])=[CH:19][CH:18]=[C:17]([C:23]([F:26])([F:25])[F:24])[CH:16]=2)=[O:11])[CH3:8]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
5.6 ml (2.8 mmol, 2M in THF) (2-methylprop-1-enyl)magnesium bromide was added in drops at 0° C. to a solution of 600 mg (1.4 mmol) 4-methyl-7-(trifluoromethyl)-2-(trifluoromethylsulfonyl-oxy)quinoline-3-carboxylic acid ethyl ester and 75 mg (0.1 mmol) Ni(dppp)Cl2 in THF (10 ml). The mixture was subsequently stirred for 16 h at RT and thereafter quenched at 0° C. with a sat. aq. NH4Cl sol. It was then extracted with EtOAc and the organic phase was washed with water and brine, dried over Na2SO4 and concentrated in a vacuum. After CC (EtOAc/hexane 1:19) of the residue, 200 mg (0.6 mmol, 43%) 4-methyl-2-(2-methylprop-1-enyl)-7-(trifluoromethyl)quinoline-3-carboxylic acid ethyl ester was obtained.
Workup
- customquenched at 0° C. with a sat. aq. NH4Cl sol. It
- extractionwas then extracted with EtOAc
- washthe organic phase was washed with water and brine
- dry with materialdried over Na2SO4
- concentrationconcentrated in a vacuum
Sources & evidence
- ORD record
- ord-559ae8e3fdb34b5b8bf17b53479c3a69
- Source dataset
- uspto-grants-2013_05
- Patent number
- US08445512B2
Reaction notes
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