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CAS No. : | 854778-31-7 | MDL No. : | MFCD08056358 |
Formula : | C7H8BFO3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | LUJMSRVFSBMEOY-UHFFFAOYSA-N |
M.W : | 169.95 | Pubchem ID : | 44558185 |
Synonyms : |
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | 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 |
---|---|---|
35% | To a solution of 7B (2.7 g, 13.1 mmol) in THF (25 mL) at -78 C. was added n-BuLi (1.6 M in hexanes, 11.0 mL, 17.7 mmol). The mixture was stirred at -78 C. for 40 min before trimethyl borate (2.7 mL, 24.3 mmol) was added. The reaction was left stirring from -78 C. to rt over 18 h. It was quenched with 1.0 N HCl (40 mL), extracted with EtOAc, washed with brine and dried over Na2SO4. After evaporation of the solvent, the crude solid product was triturated with EtOAc/hexanes (1:4). After filtration, 7C (0.75 g, 35% yield) was collected as a white solid. 1H NMR (400 MHz, Methanol-d4) delta ppm 3.86 (s, 3H) 7.03-7.45 (m, 3H). | |
35% | To a solution of 69A (2.7 g, 13.1 mmol) in THF (25 mL) at -78 C. was added n-BuLi (1.6 M in hexanes, 11.0 mL, 17.7 mmol). The mixture was stirred at -78 C. for 40 min before trimethyl borate (2.7 mL, 24.3 mmol) was added. The reaction was left stirring from -78 C. to rt over 18 h. It was quenched with 1.0 N HCl (40 mL), extracted with EtOAc, washed with brine and dried over Na2SO4. After evaporation of the solvent, the crude solid product was triturated with EtOAc/hexanes (1:4). After filtration, 69B (0.75 g, 35% yield) was collected as a white solid. 1H NMR (400 MHz, Methanol-d4) delta ppm 3.86 (s, 3 H) 7.03-7.45 (m, 3 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With tripotassium phosphate tribasic; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II) dichloromethane adduct; In N,N-dimethyl-formamide; at 60℃; for 3h;Inert atmosphere; | A mixture of <strong>[6627-22-1]methyl 6-chloropyrimidine-4-carboxylate</strong> (250 mg, 1.45 mmol), (4-fluoro-3-10 methoxyphenyl)boronic acid (492 mg, 2.90 mmol), dichloro[1,1'- bis(diphenylphosphino)ferrocene]palladium dichloromethane adduct (106 mg, 0.145 mmol) and potassium phosphate (923 mg, 4.35 mmol) in DMF (12.5 mL) was purged with argon and heated in a sealed tube at 60 C for 3 h. After this time, the reaction mixture was concentrated under reduced pressure. The residue obtained was partitioned between EtOAc (50 mL) and water (50 mL), and the layers were separated. The aqueous layer was extracted with EtOAc (2 x 100 mL), and the combined organic layers were washed with water (100 mL) and brine (100 mL), dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue obtained was purified twice by FCC (Silica, 0-5% 5 MeOH in DCM) to give the title compound. m/z (ES+) (M+H)+ 263.1.1H NMR (300 MHz, DMSO- d6) δ 9.41 (d, J = 1.5 Hz, 1H), 8.59 (d, J = 1.2 Hz, 1H), 8.03 (dd, J = 8.4, 2.1 Hz, 1H), 7.96 - 7.91 (m, 1H), 7.42 (dd, J = 11.1, 8.4 Hz, 1H), 3.98 (s, 3H), 3.96 (s, 3H). | |
With tripotassium phosphate tribasic; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II) dichloromethane adduct; In N,N-dimethyl-formamide; at 60℃; for 3h;Inert atmosphere; | A mixture of <strong>[6627-22-1]methyl 6-chloropyrimidine-4-carboxylate</strong> (250 mg, 1.45 mmol), (4-fluoro-3-10 methoxyphenyl)boronic acid (492 mg, 2.90 mmol), dichloro[1,1'- bis(diphenylphosphino)ferrocene]palladium dichloromethane adduct (106 mg, 0.145 mmol) and potassium phosphate (923 mg, 4.35 mmol) in DMF (12.5 mL) was purged with argon and heated in a sealed tube at 60 C for 3 h. After this time, the reaction mixture was concentrated under reduced pressure. The residue obtained was partitioned between EtOAc (50 mL) and water (50 mL), and the layers were separated. The aqueous layer was extracted with EtOAc (2 x 100 mL), and the combined organic layers were washed with water (100 mL) and brine (100 mL), dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue obtained was purified twice by FCC (Silica, 0-5% 5 MeOH in DCM) to give the title compound. m/z (ES+) (M+H)+ 263.1.1H NMR (300 MHz, DMSO- d6) δ 9.41 (d, J = 1.5 Hz, 1H), 8.59 (d, J = 1.2 Hz, 1H), 8.03 (dd, J = 8.4, 2.1 Hz, 1H), 7.96 - 7.91 (m, 1H), 7.42 (dd, J = 11.1, 8.4 Hz, 1H), 3.98 (s, 3H), 3.96 (s, 3H). |
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