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CAS No. : | 171364-83-3 | MDL No. : | MFCD02179437 |
Formula : | C12H16BNO4 | Boiling Point : | - |
Linear Structure Formula : | (O2NC6H4)BO2C2(CH3)4 | InChI Key : | LUWACRUAJXZANC-UHFFFAOYSA-N |
M.W : | 249.07 | Pubchem ID : | 2773555 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-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 |
---|---|---|
455 mg | With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate; In water; dimethyl sulfoxide; | The titled compound was prepared by the reaction of <strong>[13534-90-2]3,4-dibromopyridine</strong> (1.01 g, 4.26 mmol) with 4-nitrophenylboronic acid pinacol ester (1.06 g, 4.26 mmol) using cesium carbonate (2.07 g, 6.39 mmol) and [l, -bis(diphenylphosphino)ferrocene]dichloropalladium (II) (155 mg, 0.21 mmol) in a mixture of DMSO and water (20 mL, 3: 1) as per the procedure described in Step 1 of Intermediate 1 to yield 455 mg of the product; 1H NMR (300 MHz, CDC13) delta 7.33 (d, 7 = 4.8 Hz, 1H), 7.63 (d, 7 = 8.7 Hz, 2H), 8.35 (d, 7 = 8.7 Hz, 2H), 8.64 (d, 7 = 5.1 Hz, 1H), 8.89 (s, 1H) ; ESI-MS (m/z) 281 (M+2H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
9.3 g | Example 1 Compound 3 (36.0 g, 0.19 mol) was dissolved in 190 mL of methylene chloride under a nitrogen atmosphere,Diisopropylethylamine (27.0 g, 0.21 mol) was added and the temperature was lowered to -60 C. Trifluoromethanesulfonic anhydride (59.2 g,0.21 mol) was added and reacted at this temperature. After the reaction, water was added, the temperature was raised to room temperature, the mixture was extracted with ethyl acetate, and saturated sodium bicarbonateAfter washing and drying of the organic phase, the solvent was distilled off under reduced pressure to give 44.5 g of compound 3 as a light yellow solid.Example 2 A mixture of compound 3 (39.0 g, 0.12 p-nitrophenyl boronate mol) under nitrogen was added 130 mL of tetrahydrofuranAfter dissolution, (31.4 g, 0.13 mol), palladium tetrakistriphenylphosphine (6.9 g, 6.0 mmol), potassium carbonate(33.1 g, 0.13 mol) and heated to reflux temperature and reacted at this temperature for 8 hours, after which time the system was lowered to roomThe reaction solution was filtered through celite and the filtrate was evaporated under reduced pressure to a partial solvent, the crystals precipitated at low temperature, filtered to give a mixture of compounds 5,6The compound was 37.5 g as a light brown solid.Example 3 In an autoclave, 110 mL of methanol was added to a mixture of compounds 5 and 6 (19.0 g, 0.065 mol), 30 mL of acetic acid was added, 1.5 g of palladium hydroxide was added,After the introduction of hydrogen, after 12 at atmospheric pressure for 24 hours, after the reaction,The solid was filtered off and most of the methanol in the filtrate was evaporated under reduced pressure. 130 mL of 1 mL sodium hydroxide solution was added and the mixture was stirred for 20 minutes.The mixture was extracted twice with ethyl acetate (2 * 100 mL), the organic phase was washed once with saturated citric acid (100 mL) and the organic phase was washed with anhydrous sodium sulfateDrying, the organic phase pressure steaming to give a pale yellow solid 9.3g. |
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