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Following the procedure of Example 3 the following halo substituted nitrobenzene compounds:2-bromo-3-chloro-1-nitrobenzene2-bromo-3-iodo-1-nitrobenzene3-bromo-2-iodo-1-nitrobenzene3-chloro-2-fluoro-1-nitrobenzene3-chloro-2-iodo-1-nitrobenzene...
With tetrakis(triphenylphosphine) palladium(0); caesium carbonate; In ethanol; water; toluene; at 120℃; for 5.0h;
1) Preparation of compound 1-1 After introducing compoundA(36.0g, 152.3mmol), 2-(4,4,5,5-tetramethyl-1,3,2-dioxaboran-2-yl)aniline (40g, 182.7mmol), tetrakis(triphenylphosphine)palladium (5.28g, 4.6mmol), cesium carbonate (124.0g, 380.6mmol), toluene (760mL), EtOH (190mL), and distilled water (190mL) into a reaction vessel, the mixture was stirred at 120°C for 5 hours. After completion of the reaction, the mixture was washed with distilled water and extracted with ethyl acetate. The obtained organic layer was dried with magnesium sulfate and the solvent was removed therefrom by a rotary evaporator. The products were purified by column chromatography to obtain compound1-1(19.3g, yield: 50.4percent).
With tetrakis(triphenylphosphine) palladium(0); caesium carbonate; In ethanol; o-xylene; for 12.0h;Reflux;
2-bromo- 1 -chloro-3-nitrobenzene (74g, 31 5mmol), (1 -fluoro-2-naphthalenyl)boronic acid (50g, 263mmo1), tetrakis(triphenylphosphine)palladium (0) (Pd(PPh3)4) (15g, l3mmol), 2M cesium carbonate (257g, 789mmo1), o-xylene (l600mL), and ethanol (400mL) were poured into a flask, and dissolved, and then refluxed for 12 hours. After completion of the reaction, an organic layer was extracted with ethyl acetate. The organic extract was dried on magnesium sulfate, and purified by column chromatography to obtain compound 5-1 (36g, yield: 47percent).
With tetrakis(triphenylphosphine) palladium(0); caesium carbonate; In ethanol; toluene; for 12.0h;Reflux;
2-bromo- 1 -chloro-3-nitrobenzene (56g, 234mmo1), 2-chlorophenylboronic acid (74g, 476mmol), tetrakis(triphenylphosphine)palladium (0) (Pd(PPh3)4) (13g, 1 1.9mmol), 2M cesium carbonate (194g, 596mmoL), toluene (l200mL), and ethanol (300mL) were poured into a flask, and dissolved, and then refluxed for 12 hours. After completion of the reaction, an organic layer was extracted with ethyl acetate. The organic extract was dried on magnesium sulfate, and purified by column chromatography to obtain compound 1-1 (51g, yield: 80percent).
To a solution of <strong>[19128-48-4]2-bromo-1-chloro-3-nitro-benzene</strong> (4.50 g, 19.0 mmol) in THF (90 ml)20 was added vinyl magnesium bromide (9.99 g, 76.1 mmol) dropwise at -78C and thereaction mixture was stirred at the same temperature for 2h. Progress of the reaction wasmonitored by TLC and LCMS. The reaction was repeated at 4.5 g scale and the crudemixture of 2 reactions was clubbed. After completion, the reaction mixture was quenchedwith saturated NH4CI (500 ml), diluted with H20 (500 ml) and extracted with EtOAc (100025 ml). The organic layer was separated, dried over anhydrous Na2S04 and concentratedunder vacuum. The crude obtained was purified by column chromatography (silica, 100-200 mesh, 2% EtOAc in hexanes) to afford 7-bromo-6-chloro-1 H-indole Xl-7 (3.05 g) as ayellow solid.Yield: 33%30 Basic LCMS Method 2 (ES-): 228.00 (M-H)-, 96 % purity1H NMR (400 MHz, DMSO-d6) o 6.59 (d, J=1.96 Hz, 1 H) 7.18 (d, J=8.31 Hz, 1 H) 7.41-7.45 (m, 1 H) 7.57 (d, J=8.31 Hz, 1 H) 11.48 (brs, 1 H)
Step-1: Synthesis of 7-bromo-6-chloro-1H-indole XI-3a To a solution of <strong>[19128-48-4]2-bromo-1-chloro-3-nitro-benzene</strong> (4.50 g, 19.0 mmol) in THF (90 mL) was added vinyl magnesium bromide (9.99 g, 76.1 mmol) dropwise at -78C and the reaction mixture was stirred at the same temperature for 2h. Progress of the reaction was monitored by TLC and LCMS.
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; at 65℃;
SM-15 (1 equiv), 2-Bromo-1-chloro-3-nitrobenzene (1 equiv), Pd(PPh3)4 (0.03 equiv), K2CO3 (3 equiv), THF (8 mL / SM-15 1 mmol), Water (4ml / 0.5 mmol) was added and the reaction proceeds at 65 C. After completion of the reaction, the mixture was extracted with CH2Cl2 and water, and then the organic layer was dried over MgSO4 and concentrated. After completion of the reaction, the mixture was extracted with CH 2 Cl 2 and water, and then the organic layer was dried over MgSO 4 and concentrated. (Yield 83%)
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; at 65℃;
SM-8 (1 equiv), 2-Bromo-1-chloro-3-nitrobenzene (1 equiv), Pd(PPh3)4 (0.03 equiv), K2CO3 (3 equiv), THF (8 mL / SM-8 1 mmol) , Water (4ml / 0.5 mmol) was added and the reaction proceeds at 65 C. After completion of the reaction, the mixture was extracted with CH2Cl2 and water, and then the organic layer was dried over MgSO4 and concentrated. Thereafter, the concentrate was separated by a silica gel column and recrystallized to obtain SM-9. (Yield 72%).
With tetrakis-(triphenylphosphine)-palladium; potassium carbonate In ethanol; water monomer; toluene at 60 - 70℃; Inert atmosphere;
1. Synthesis of Compound A
110 mmol of compound 2-bromo-3-chloronitrobenzene, 250 mmol of potassium carbonate, 500 g of toluene, and 100 g of purified water were added to the reaction flask, stirred, and 0.1 mmol of tetrakis (triphenylphosphine) palladium was added under nitrogen protection.After adding above-mentioned materials, be warming up to 6070 , add dropwise the solution that 100mmol 4-dibenzothiazole boronic acid and 100g ethanol are made into, after TLC tracking detects that there is no 2-bromo-3-chloronitrobenzene remaining, let stand The lower reaction water phase was separated, the water separation was completed, and the remaining organic phase was washed with purified water until neutral, then a desiccant was added, and the mixture was passed through a silica gel column at atmospheric pressure.After passing through the column, use 200 g of toluene each time to wash the silica gel column 3 times.After rinsing, the eluent and the column liquid were combined and desolventized under negative pressure to obtain 78 mmol of compound C with a yield of 78%.
With tetrakis-(triphenylphosphine)-palladium; potassium carbonate In tetrahydrofuran; water monomer at 65℃; for 12h;
2 Synthesis Example 2: Synthesis of Compound A5
Add 100mmol of 2-bromo-3-chloro-nitrobenzene, 100mmol of1-Dibenzothiophene boronic acid, 40 g potassium carbonate (300 mmol), 800 ml THF and 200 ml water, and 1 mol% Pd(PPh3)4 is added. React at 65°C for 12h. After the completion of the reaction, the reaction was stopped, and the reactant was cooled to room temperature, water was added, filtered, and washed with water. The obtained solid was recrystallized and purified with toluene to obtain a yellow powder M1. Wherein, the amount of Pd(PPh3)4 added is 1 mol% of 2-bromo-3-chloro-nitrobenzene.
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