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CAS No. : | 171364-82-2 | MDL No. : | MFCD03093897 |
Formula : | C13H16BNO2 | Boiling Point : | - |
Linear Structure Formula : | NCC6H4B(OC(CH3)2C(CH3)2O) | InChI Key : | HOPDTPGXBZCBNP-UHFFFAOYSA-N |
M.W : | 229.08 | Pubchem ID : | 2734625 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H332-H335 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95.3% | With tris-(dibenzylideneacetone)dipalladium(0); tri(m-tolyl)phosphine; In tetrahydrofuran; at 60℃;Inert atmosphere; | Under the protection of argon, 117.9 g (0.5 mol) of 1,4-dibromobenzene and 91.6 g of 4-cyanobenzoic acid pinacol ester were sequentially added.(0.4 mol), potassium phosphate trihydrate 213.1 g (0.8 mol), tris(m-tolyl)phosphine 0.3 g (1 mmol), tetrahydrofuran 500 mL,Adding tris(dibenzylideneacetone)dipalladium (Pd2(dba) 3183.1 mg (0.2 mmol), controlling the reaction temperature at 60 C, HPLC detectionAfter completion, 700 mL of water was added to the reaction solution, and the mixture was extracted three times with 300 mL of dichloromethane, and the organic phases were combined and dried over anhydrous magnesium sulfate.Filtration and recovery of solvent under reduced pressure gave a pale yellow solid, 98.3 g after drying, purity 99.1% (HPLC), yield 95.3%, |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
350 mg | With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate; In 1,4-dioxane; water; at 100℃; for 18h; | To a solution of <strong>[630125-49-4]1-bromo-3-nitro-5-(trifluoromethyl)benzene</strong> (250 mg, 0.92 mmol) in 1,4- dioxane (10 mL) and water (1.0 mL) were added 4-(4,4,5 ,5-tetramethyl- 1,3 ,2-dioxaborolan- 2-yl)benzonitrile (215 mg, 0.94 mmol), [1,1?- bis(diphenylphosphino)ferrocene]dichloropalladium(II) complex with dichloromethane (39 mg, 0.05 mmol) and potassium carbonate (269 mg, 1.95 mmol) and the mixture was heated at100 C for 18 h. The mixture was cooled to RT and diluted with ethyl acetate. The solution was filtered through celite. The filtrate was washed with water followed by brine, dried over anhydrous sodium sulfate, filtered and concentrated. The residue obtained was purified by silica gel column chromatography to yield 350 mg of the desired compound. ?H NMR (400 MHz, DMSO-d6) oe 8.03 (dd, J, = 1.6 Hz, J2 = 3.6 Hz, 2H), 8.14 (dd, J, = 2.0 Hz, J2 = 6.4Hz, 2H), 8.60 (s, 2H), 8.81 (t, J 1.6 Hz, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
0.3 g | With tetrakis(triphenylphosphine) palladium(0); tricaprylylmethylammonium chloride; sodium carbonate; In tetrahydrofuran; water; for 30h;Inert atmosphere; Reflux; | Under argon atmosphere,In a reaction vessel, 2.0 g of a compound represented by formula (I-2-1),1.3 g of a compound represented by the formula (I-2-2)2.9 g of a compound represented by formula (I-2-3),1.3 g sodium carbonate, 12 mL water,30 mL of tetrahydrofuran,Aliquot 336 (manufactured by Aldrich) 0.3 g,0.1 g of tetrakis (triphenylphosphine) palladium (0) was added, and the mixture was heated to reflux for 30 hours.It was diluted with dichloromethane and separated.After washing the organic layer twice with water,Purification was performed by column chromatography (silica gel, chloroform). Preparative thin layer chromatography (silica gel, 2 mm thick,Hexane / ethyl acetate (3: 1),Purification is carried out by column chromatography (silica gel, toluene) and recrystallization (toluene / ethanol).0.3 g of a compound represented by the formula (I-2) was obtained. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
152 mg | With bis(di-tert-?butyl(4-?dimethylaminophenyl)?phosphine)?dichloropalladium(II); potassium carbonate; In methanol; toluene; at 65℃; for 2.0h;Cooling with ice; | 2-Bromo-5-fluoroisonicotinic acid methyl ester crude product obtained in the previous step (234 mg),4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) benzonitrile(229 mg),Bis (di-tert-butyl (4-dimethylaminophenyl) phosphine) dichloropalladium (II) (14 mg) and potassium carbonate (415 mg) were mixed in toluene (3 mL) and methanol (2 mL).The reaction mixture was stirred at 65 C. for 2 hours.Under ice-cooling, 1N hydrochloric acid was added to the reaction mixture,The pH was adjusted to 7. Ethyl acetate was added to the reaction mixture, and the mixture was washed successively with water and saturated aqueous sodium chloride solution.The organic layer was dried with sodium sulfate.Sodium sulfate was removed by filtration, and the filtrate was concentrated under reduced pressure.The obtained residue was purified by silica gel column chromatography (hexane: ethyl acetate = 10: 1 to 5: 1). The eluate was concentrated, and hexane was added to the obtained residue. The precipitated solid was collected by filtration to give the title compound (152 mg). |
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