Diisopropylethylamine → 4-(4-Fluorophenyl)-7-[(4-formyl-1H-pyrazol-1-yl)methyl]-2-quinolinecarbonitrile
Reaction equation
Br[CH2:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([C:15]3[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=3)=[CH:8][C:9]([C:13]#[N:14])=[N:10]2)=[CH:5][CH:4]=1.CCN(C(C)C)C(C)C.[NH:31]1[CH:35]=[C:34]([CH:36]=[O:37])[CH:33]=[N:32]1>C(#N)C>[F:21][C:18]1[CH:19]=[CH:20][C:15]([C:7]2[C:6]3[C:11](=[CH:12][C:3]([CH2:2][N:31]4[CH:35]=[C:34]([CH:36]=[O:37])[CH:33]=[N:32]4)=[CH:4][CH:5]=3)[N:10]=[C:9]([C:13]#[N:14])[CH:8]=2)=[CH:16][CH:17]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
7-(Bromomethyl)-4-(4-fluorophenyl)quinoline-2-carbonitrile (2-1, 100.0 mg, 0.293 mmol, 1.0 equiv.), DIEA (0.051 ml, 0.293 mmol, 1.0 equiv.), and 1-H-pyrazole-4-carbaldehyde (33.8 mg, 0.352 mmol, 1.2 equiv.) were added to acetonitrile (1.0 mL) in a microwave reaction vessel and the resulting mixture was irradiated with microwave at 180° C. for 30 minutes. The reaction mixture was cooled and concentrated and the residue was purified by reverse phase HPLC (H2O/CH3CN gradient w/0.1% TFA modifier) to afford 4-(4-fluorophenyl)-7-[(4-formyl-1H-pyrazol-1-yl)methyl]quinoline-2-carbonitrile (3-8, 55.0 mg, 52.7%) as a colorless solid. LRMS m/z (M+H)+ 357.1 found, 357.1 required.
Workup
- customthe resulting mixture was irradiated with microwave at 180° C. for 30 minutes
- temperatureThe reaction mixture was cooled
- concentrationconcentrated
- customthe residue was purified by reverse phase HPLC (H2O/CH3CN gradient w/0.1% TFA modifier)
Sources & evidence
- ORD record
- ord-a46d787f7afd4bcf8064fef62079f549
- Source dataset
- uspto-grants-2016_03
- Patent number
- US09278960B2
Reaction notes
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