2-Cyclopropyl-4-(4-fluorophenyl)-3-quinolinecarboxaldehyde

Under the protection of nitrogen, in a 500ml round bottom flask, add 10g (0.0185mol) compound III, 100ml DMF, 5.65g (0.0194mol) compound V, 3.53g (0.0333mol) sodium carbonate, start stirring, slowly warm up to 80C , incubate at 80C -85C for 1h, then cool to room temperature, Add 200ml of water and 200ml of toluene, stir for 30 minutes, separate layers, The lower aqueous layer was extracted with 200ml of toluene, and the upper toluene layer was combined, Wash with 50ml water once, the toluene layer is desolvated to dryness under reduced pressure, add 50ml methanol, Stir and heat to complete dissolution, lower the temperature and crystallize, suction filter, filter solid and dry, get7.65g (0.0148mol)(4R, 6S)-(E)-6-[2-cyclopropyl-4- (4-fluorophenyl)-quinolin-3-yl]-vinyl]-2, 2-dimethyl-1, 3-dioxane-4-acetic acid tert-butyl ester, product purity 99.0%, The pure yield was 79.2%.Under the protection of nitrogen, in a 500ml round-bottom flask, add 200ml toluene, 10.4g (0.082mol) oxalyl chloride, start stirring, and lower the temperature to about -60C , Add 18.6g (0.238mol) DMSO dropwise, the control temperature should not exceed -15C , after dripping, keep warm at -15C for 30 minutes, 20g (0.068mol) of compound IV in toluene (50ml) was added dropwise, Control the temperature not to exceed -15C , keep warm at -15C for 3 hours after dropping, Slowly add 20.7g (0.205mol) of triethylamine, control the temperature not to exceed 10C , After dripping, keep warm at 5C for 30 minutes, add 100ml of water, stir and separate, The lower water layer was extracted with 100ml toluene, and the upper toluene layer was combined.Wash it once with 50ml of water, the toluene layer is desolvated to dryness, add 40ml of n-heptane, Heat to complete dissolution, lower the temperature and crystallize, suction filtration, filter solid drying17.9 g (0.061 mol) of compound V was obtained with a product purity of 99.2% and a pure yield of 89.0%.Example 19: Preparation of General procedure: A mixture of acetophenone 2a (18.88 mmol), Quinoline aldehyde 1 (17.16 mmol) andKOH (25.74 mmol) was refluxed in methanol (75 mL) for 4 hrs. Completion of the reactionwas evidenced by TLC analysis. After completion of the reaction, the reaction mixturewas cooled to 0 C. The resulting solid filtered and the solid recrystallized frommethanol. Obtained as an off - white solid (5.745 g) in 85% yield.General procedure: A mixture of acetophenone 2a (18.88 mmol), Quinoline aldehyde 1 (17.16 mmol) andKOH (25.74 mmol) was refluxed in methanol (75 mL) for 4 hrs. Completion of the reactionwas evidenced by TLC analysis. After completion of the reaction, the reaction mixturewas cooled to 0 C. The resulting solid filtered and the solid recrystallized frommethanol. Obtained as an off - white solid (5.745 g) in 85% yield.General procedure: A mixture of acetophenone 2a (18.88 mmol), Quinoline aldehyde 1 (17.16 mmol) andKOH (25.74 mmol) was refluxed in methanol (75 mL) for 4 hrs. Completion of the reactionwas evidenced by TLC analysis. After completion of the reaction, the reaction mixturewas cooled to 0 C. The resulting solid filtered and the solid recrystallized frommethanol. Obtained as an off - white solid (5.745 g) in 85% yield.General procedure: A mixture of acetophenone 2a (18.88 mmol), Quinoline aldehyde 1 (17.16 mmol) andKOH (25.74 mmol) was refluxed in methanol (75 mL) for 4 hrs. Completion of the reactionwas evidenced by TLC analysis. After completion of the reaction, the reaction mixturewas cooled to 0 C. The resulting solid filtered and the solid recrystallized frommethanol. Obtained as an off - white solid (5.745 g) in 85% yield.

Molecular Weight:291.3
XLogP3:4
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:3
Exact Mass:291.105942232
Monoisotopic Mass:291.105942232
Topological Polar Surface Area:30
Heavy Atom Count:22
Complexity:402
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes