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With sodium hydroxide; hydroxylamine-O-sulfonic acid; In water; acetonitrile; for 1h;Sonication;
General procedure: Reactions facilitated by sonication were performed on a 1.0 mmol scale. Arylboronic acid 3 (1.0 equiv) and MeCN (5.0 mL) were added to a 25 mL microwave vial equipped with a stir bar, followed by HSA (1.5 equiv) and aq 1 M NaOH (5 equiv). The mixture was capped and set to stir for 5 min, then placed in an ultrasonic cleaner for 30 min (35 kHz, 90 W), at which time the vial was removed and a small aliquot was taken for reaction monitoring via HPLC analysis. The mixture was then placed back in the sonication bath for 30 min. This process was repeated until the reaction had gone to completion, or the reaction failed to progress, as monitored by HPLC. The reaction mixture was diluted with H2O (30 mL) and extracted with EtOAc (2 × 30mL). The combined organic extracts were dried (Na2SO4) and concentrated in vacuo. The residue was purified by flash chromatography (EtOAc/hexanes) to afford the desired amine product 2.
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate; In tetrahydrofuran; water; at 100℃; for 24h;Inert atmosphere; Schlenk technique;
Under an argon atmosphere, in a Schlenk flask,Followed by loading 3mmol of <strong>[10485-09-3]2-bromoindene</strong> (Shanghai Bi Pharmaceutical Technology Co., Ltd.)1.5 mmol of 2,6-dimethoxyphenylboronic acid (Shanghai Biomedicine Technology Co., Ltd.), 3 mmol% of palladium acetate, 6 mmol% of S-Phos and 3 mmol of potassium phosphate,A mixture of 20 mL of tetrahydrofuran and 10 mL of water was added to dissolve the reaction. The reaction was carried out at 100 C for 24 hours,After cooling, the reaction mixture was extracted with ethyl acetate, the organic phase was dried over anhydrous sodium sulfate, the organic solvent was removed to dryness,Column chromatography on petroleum ether (Rf = 0.8) gave 2- (2,6-dimethoxyphenyl) indene,Yield 79%
6-chloro-2-(2,6-dimethoxyphenyl)pyridin-3-amine[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
Ca. 100%
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,2-dimethoxyethane; water; at 90℃; for 3h;Inert atmosphere;
<strong>[1050501-88-6]2-bromo-6-chloropyridin-3-amine</strong> (4.52 g, 21.79 mmol), (2,6-dimethoxyphenyl)boronic acid (4.76 g, 26.1 mmol), Na2CO3 (4.62 g, 43.6 mmol), 1,2-dimethoxyethane (80 mL), and water (40 mL) were added to a 500 mL two-necked round-bottom flask equipped with a magnetic stir bar. The reaction mixture was degassed with N2 for 15 minutes. After this time. Pd(PPh3)4 (1.26 g, 1.09 mmol) was added and the reaction flask was placed into an oil bath and gradually heated to 90 C. for 3 hours. The reaction mixture was then cooled to room temperature (22 C.) and then diluted with ethyl acetate (EtOAc). The resulting mixture was then washed with brine and the separated organic layer were dried over Na2SO4, filtered and concentrated in vacuo. The crude product was triturated with CH2Cl2 to yield the title compound as pale pink solid (4.0 g). The remaining filtrate was purified via flash chromatography on a 200 g column (50-75% EtOAc/Heptanes) to provide 6-chloro-2-(2,6-dimethoxyphenyl)pyridin-3-amine as a white solid (2.5 g) (overall yield 100% yield).
A mixture of <strong>[16932-45-9]2-bromo-1,3-dimethoxybenzene</strong> 0.018mol was dissolved in 100ml, dry THF, was added 500ml three dried flask, N2Under the protection of -78 reaction 30min, was slowly added dropwise n-butyl lithium 0.027mol, after the completion of the dropping kept -78 reaction 3h, then slowly dropped triisopropyl borate 0.02mol, after the completion of the dropping reaction was held at - 78 reaction 2h, gradually warming to room temperature, the reaction overnight. after the reaction monitored by TLC, the reaction solution was slowly quenched with water, extracted and evaporated to dryness to give (2,6-dimethoxyphenyl) boronic acid (formula III'-1 shown) 0.0144mol, 80% yield.
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