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Example 34 In a similar manner to the preparation of the compound of Example 33-1, 6-bromo-3-methylquinoline (1.04 g, 75%) was obtained from <strong>[29124-57-0]2-amino-5-bromobenzaldehyde</strong> (1.25 g). 1H NMR (CDCl3, 300 MHz) delta 8.77 (d, 1H, J=2.0 Hz), 7.93 (d, 1H, J=9.0 Hz), 7.91 (d, 1H, J=2.2 Hz), 7.83 (d, 1H, J=2.0 Hz), 7.71 (dd, 1H, J=2.2, 9.0 Hz), 2.53 (s, 3H).
(34-1) In a similar manner to the preparation of the compound of Example 33-1, 6-bromo-3-methylquinoline (1.04 g, 75 %) was obtained from 2-amino-5-bromobenzaldehyde (1.25 g).
Stir,200 mL of ethanol and 19.9 g of the compound of Formula II were added to the reaction flask.The temperature was raised to 55 C, 17.38 g of pyridine was added dropwise, the temperature was controlled at 55 C, and the mixture was stirred for 0.5 h.Add 8.7 g of propionaldehyde, reflux the reaction, monitor the reaction completely, concentrate,Add water to the concentrate, stir, pass through the liquid, crystallize, filter, and filter cake with water.Drying gave 19.23 g of an off white solid in a yield of 87.0%.
With palladium diacetate; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In 1,4-dioxane; at 80℃;
220 mL of dioxane was added to the reaction flask, and 22.1 g of the compound of the formula III and 21.72 g of the formula were added with stirring.Compound shown in IV, 1.5575g BINAP, 0.4928g Pd(AcO)2 and 48.9g Cs2CO3, heated to 75 C, reaction, monitoringAfter the reaction was completed, the dioxane was distilled off under reduced pressure, water (100 mL) was added, and the filtrate was extracted three times with ethyl acetate.The organic phase is washed with aqueous sodium hydrogencarbonate solution and aqueous sodium chloride solution, dried over anhydrous sodium sulfate and concentrated, ethyl acetate:The ether was recrystallized 1:6.5 to give 24.71 g of a solid, yield 76.7 %
3-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinoline[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
79.2%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,2-dimethoxyethane; at 80℃; for 2.0h;Inert atmosphere;
6-Bromo-3-methylquinoline 28a (250 mg, 1.13 mmol, prepared according to the method disclosed in the patent application "WO2006132739A2"), bis(pinacolato)diboron (429 mg, 1.69 mmol), [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium (165 mg, 0.225 mmol) and potassium acetate (331 mg, 3.38 mmol) were dissolved successively in 20 mL of dimethyl ether under an argon atmosphere. The reaction solution was heated to 80C, and stirred for 2 hours. The reaction was stopped, and the reaction solution was cooled to room temperature and filtrated. The filtrate was concentrated under reduced pressure, and the residue was purified by CombiFlash rapid preparation instrument with elution system B to obtain the title product 28b (240 mg), yield: 79.2%. MS m/z (ESI): 270.1 [M+1].
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