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CAS No. : | 762262-09-9 | MDL No. : | MFCD07368877 |
Formula : | C6H8BNO3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | DHQMUJSACXTPEA-UHFFFAOYSA-N |
M.W : | 152.94 | Pubchem ID : | 23546919 |
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: |
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* 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 |
---|---|---|
With sodium carbonate;bis-triphenylphosphine-palladium(II) chloride; In 1,4-dioxane; water; at 100.0℃; for 2.0h;Microwave radiation; | To a solution of <strong>[886371-28-4]3-bromo-6-chloro-imidazo[1,2-a]pyridine</strong> (1 eq, 0.72 mmol, 0.2 g), 2- methoxypyrid-4-yl boronic acid (1.0 eq, 0.72 mmol, 0.11 g), Na2COs (2 eq, 1.44 mmol, 0.152 g) in dioxane (0.6 ml) and water (0.2 ml), under an inert atmosphere of argon is added bis(triphenylphosphine)palladium II chloride (50 mg). The reaction mixture is heated using microwave radiation at 100 C for 2 hours. The mixture is diluted with H2O (50 ml) and extracted with EtOAc. The combined organic portions are washed with brine, dried (MgStheta4) and concentrated in vacuo. The residue is <n="120"/>purified by flash chromatography on silica eluting with 0-25% EtOAc in iso-hexane to afford the title compound; [M+H]+ =260 (262). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | With potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In 1,4-dioxane; water; at 90.0℃; for 4.0h;Inert atmosphere; | A solution of (2-methoxypyridin-4-yl)boronic acid (75 mg, 0.490 mmol), 4- bromo-2-(difluoromethyl)-l-fluorobenzene (121 mg, 0.539 mmol), potassium phosphate tribasic (312 mg, 1.471 mmol) and PdCl2(dppf)-CH2Cl2 adduct (20.02 mg, 0.025 mmol) in 1,4-dioxane (3 mL) and water (0.5 mL) was purged with nitrogen and heated to 90 C for 4 h. The reaction mixture was diluted with ethyl acetate (10 mL). The black suspension was filtered through diatomaceous earth (Celite) and the bed was washed with ethyl acetate (10 mL). The residue was purified via silica gel chromatography (15% pet ether: ethyl acetate) to afford 4-(3-(difluoromethyl)-4- fluorophenyl)-2-methoxypyridine (100 mg, 0.363 mmol, 74% yield) as a brown solid. LCMS (ESI) m/e 254.0 [(M+H)+, calcd for C13H11F3NO 254.1]; LC/MS retention time (Method C): tR = 1.02 min. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | With potassium phosphate; chloro(2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1‘-biphenyl)[2-(2’-amino-1,1‘-biphenyl’)]palladium(II); In 1,4-dioxane; water; at 100℃; for 5h;Inert atmosphere; | A mixture of 2-chloro-6-(trifluoromethyl)benzoicacid (1 g, 4.45 mmol), X-phos Pd G?. (350 mg, 0.45 mmol), 2-methoxypyridine-4-boronicacid (817 mg, 5.34 mmol) and K3PO4 (3.78 g, 17.81 mmol) in 1,4-dioxane (20 mL) and water (2 mL) were stirred at 100 C for 5 hours under an atmosphere of M2.After cooling to 25 C, the reaction mixture was diluted in water (40 mL). The aqueous layer was extracted with EtOAc (40 mL x 2). Tire combined organic layers were dried over anhydrous NaaSfL, filtered and concentrated under reduced pressure. The crude residue was purified by reverse phase chromatography (acetonitrile 27-57/0.225% FA in water) to give 2-(2-methoxypyridin-4-yl)-6- (trifluoromethyl)benzoic acid (900 mg, yield: 68%) as a white solid. TlNMR (400 MHz, CDCft): d = 8.20 (d, J = 5.6 Hz, 1H), 7.80 (d, J = 8.0 Hz, I I I). 7.67-7.63 (m, H I). 7.57 (d, J = 7.6 Hz, 111). 7.03-7.01 (m, IH), 6.86 (s, 1H), 3.95 (s, 3H), 3.42 (br, s, 1H). |
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