Reaction equation
[CH:1]1([C:4]2[C:13]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([N:21]4[CH:25]=[CH:24][CH:23]=[N:22]4)=[CH:17][CH:16]=3)=[C:12]([CH3:26])[C:11]3[C:10]([OH:27])=[CH:9][CH:8]=[C:7]([F:28])[C:6]=3[N:5]=2)[CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O.Br[CH2:41][C:42]([O:44][CH3:45])=[O:43]>O>[CH3:45][O:44][C:42](=[O:43])[CH2:41][O:27][C:10]1[CH:9]=[CH:8][C:7]([F:28])=[C:6]2[C:11]=1[C:12]([CH3:26])=[C:13]([CH2:14][C:15]1[CH:20]=[CH:19][C:18]([N:21]3[CH:25]=[CH:24][CH:23]=[N:22]3)=[CH:17][CH:16]=1)[C:4]([CH:1]1[CH2:2][CH2:3]1)=[N:5]2Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of 2-cyclopropyl-8-fluoro-4-methyl-3-(4-pyrazol-1-ylbenzyl)quinolin-5-ol (0.040 g), potassium carbonate (0.044 g) and N,N-dimethylformamide (0.21 mL) was treated with methyl bromoacetate (0.011 mL), and the resulting mixture was stirred at room temperature for 1 hour. The mixture was diluted with water (30 mL), extracted with ethyl acetate (3×10 mL), and the combined extracts were dried over magnesium sulfate. The solvent was removed under reduced pressure and the residue purified by column chromatography on silica gel, eluting with a mixture of cyclohexane and ethyl acetate (1:0 to 3:2 by volume) to afford the title compound as a yellow oil (0.034 g).
Workup
- extractionextracted with ethyl acetate (3×10 mL)
- dry with materialthe combined extracts were dried over magnesium sulfate
- customThe solvent was removed under reduced pressure
- customthe residue purified by column chromatography on silica gel
- washeluting with a mixture of cyclohexane and ethyl acetate (1:0 to 3:2 by volume)
Sources & evidence
- ORD record
- ord-2eb42a8e56ba461197f836ac43f0c4f5
- Source dataset
- uspto-grants-2013_03
- Patent number
- US08394830B2
Linked notes
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