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CAS No. : | 6942-36-5 | MDL No. : | MFCD00010867 |
Formula : | C8H6BrNO4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | VSEYYEKRZNRECT-UHFFFAOYSA-N |
M.W : | 260.04 | Pubchem ID : | 245494 |
Synonyms : |
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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 |
---|---|---|
72% | With dichlorobis(triphenylphosphine)palladium(II); potassium carbonate; In 1,2-dimethoxyethane; water; at 100℃; for 2h;Inert atmosphere; | <strong>[1002309-48-9]1-cyclobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole</strong> (1.5 g, 6.0 mmol) and methyl 2-bromo-5-nitrobenzoate (1.66 g, 6.0 mmol) in DME (30 mL) and water (15 mL) was degassed with nitrogen for 5 minutes. Bis(triphenylphosphine)-palladium(ll) dichloride (127 mg, 0.18 mmol) and potassium carbonate (2.5 g, 18.1 mmol) were added and the reaction heated with stirring at 100 C for 2 hours. The reaction mixture was cooled to room temperature, diluted with water (30 mL) and extracted with EtOAc (50 mL). The organic layer was washed with brine (2 x 30 mL), dried (Na2S04), filtered and concentrated at reduced pressure. The residue was purified by Biotage Isolera chromatography (silica gel; using a gradient of eluents; 0-50% EtOAc in heptane) to give the title compound (1.72 g, 72% yield) as a yellow oil. 1H NMR (500 MHz, DMSO-d6) delta [ppm] 8.43 (d, J = 2.5 Hz, 1 H), 8.33 (dd, J = 8.7, 2.6 Hz, 1 H), 8.20 (s, 1 H), 7.83 (d, J = 8.7 Hz, 1 H), 7.72 (s, 1 H), 4.97 - 4.81 (m, 1 H), 3.85 (s, 3H), 2.45 -2.33 (m, 2H), 1.87 - 1.76 (m, 2H). LCMS (Analytical Method A): R t= 1.19 mins, MS (ESIPos): m/z = 302 (M+H) |
72% | With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate; In 1,2-dimethoxyethane; water; at 100℃; for 2h;Inert atmosphere; | 1-Cyclobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (1.50 g, 6.0 mmol) and methyl 2-bromo-5-nitrobenzoate (1.66 g, 6.0 mmol) in DME (30 mL) and water (15 mL) was degassed with nitrogen for 5 minutes. Pd(PPh3)2Cl2 (127 mg, 0.18 mmol) and K2CO3 (2.5 g, 18.1 mmol) were then added and the reaction was heated to 100 C. for 2 hours. The reaction was then cooled to RT and diluted with water (30 mL) and extracted with EE (50 mL). The organic layer was then washed with brine (2*30 mL), dried (Na2SO4), filtered and concentrated at reduced pressure. The residue was purified by Biotage Isolera chromatography (using a gradient of eluents; 0-50% EE in heptane) to afford the title compound (1.72 g, 72% yield) as a yellow oil. 1H NMR (500 MHz, DMSO-d6) delta 8.43 (d, J=2.5 Hz, 1H), 8.33 (dd, J=8.7, 2.6 Hz, 1H), 8.20 (s, 1H), 7.83 (d, J=8.7 Hz, 1H), 7.72 (s, 1H), 4.97-4.81 (m, 1H), 3.85 (s, 3H), 2.45-2.33 (m, 4H), 1.87-1.76 (m, 2H). LCMS (Analytical Method A): Rt=1.19 min; MS (ESIPos) m/z=302 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | A mixture of <strong>[1151802-22-0]1-<strong>[1151802-22-0]cyclopropyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole</strong></strong> (1 .00 g, 4.27 mmol), methyl 2-bromo-5-nitrobenzoate (1 .01 g, 3.88 mmol), dichlorobis(triphenylphosphine)palladium(ll) (51 mg, 0.07 mmol) and potassium carbonate (1 .77 g, 12.82 mmol) were dissolved in dimethoxyethane (13 mL) and water (6.5 mL) then degassed via bubbling nitrogen gas through the solution for 10 minutes. The mixture was then heated at 100 C for 16 hours. The reaction mixture was then cooled to room temperature, diluted with EtOAc (50 mL) and washed with 2M aq. lithium hydroxide solution (20 mL), 2M aqueous hydrogen chloride solution (30 mL), saturated aqueous sodium chloride solution (20 mL), dried (MgS04), filtered and concentrated at reduced pressure giving the title compound (0.9 g, 77% yield) as a yellow solid. 1H NMR (250 MHz, DMSO-d6) delta [ppm] 13.67 (s, 1 H), 8.38 (d, J = 2.5 Hz, 1 H), 8.30 (dd, J = 8.6, 2.6 Hz, 1 H), 8.20 (s, 1 H), 7.80 (d, J = 8.6 Hz, 1 H), 7.72 (d, J = 0.6 Hz, 1 H), 3.89 - 3.72 (m, 1 H), 1.13 - 0.96 (m, 4H). LCMS (Analytical Method A): Rt = 1.03 mins; MS (ESIPos) m/z = 273.95 (M+H) |
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