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CAS No. : | 758699-74-0 | MDL No. : | MFCD07367561 |
Formula : | C12H18BNO3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | FVHUFNSLTSKBDN-UHFFFAOYSA-N |
M.W : | 235.09 | Pubchem ID : | 44118676 |
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 |
---|---|---|
63% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,2-dimethoxyethane; water; at 130.0℃; for 1.5h;Microwave irradiation; | A solution of the compound (508 mg, 1.0 mmol) obtained in Example 16-4), <strong>[758699-74-0]4-methoxypyridine-3-boronic acid pinacol ester</strong> (321 mg, 1.5 mmol), tetrakis(triphenylphosphine)palladium(0) (231 mg, 0.2 mmol), and potassium carbonate (276 mg, 2 mmol) in dimethoxyethane (4 mL) and water (1 mL) was stirred at 130C for 1.5 h under microwave irradiation. The reaction mixture was cooled to room temperature, saturated aqueous sodium hydrogencarbonate was added to the reaction mixture, the mixture was extracted with dichloromethane, and the organic layer was washed with saturated sodium chloride solution and dried with anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (Isco Combiflash, 40 g, methanol:ethyl acetate = 0:100 to 20:80, gradient) to obtain the title compound (337 mg, 63%) as a colorless solid. 1H-NMR (400 MHz, CDCl3) delta: 0.05 (3H, s), 0.07 (3H, s), 0.91 (9H, s), 1.20 (3H, s), 1.44-1.60 (2H, m), 1.62-1.69 (2H, m), 2.57 (1H, ddd, J = 15.5, 8.1, 2.2 Hz), 2.71 (1H, ddd, J = 15.5, 7.9, 2.1 Hz), 3.40 (2H, s), 3.51 (1H, d, J = 10.2 Hz), 3.55 (1H, d, J = 10.2 Hz), 3.87 (3H, s), 4.10 (1H, ddd, J = 14.5, 7.9, 2.1 Hz), 4.35 (1H, ddd, J = 14.5, 8.1, 2.2 Hz), 6.90 (1H, dd, J = 11.5, 5.9 Hz), 7.14 (2H, d, J = 8.6 Hz), 7.44 (2H, d, J = 8.6 Hz), 7.52 (1H, d, J = 3.1 Hz), 8.48 (1H, dd, J = 11.5, 5.9 Hz) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); potassium carbonate; In 1,4-dioxane; water; at 110.0℃; | A mixture of 6-bromo-lH-indazole (500 mg, 2.54 mmol), 4-methoxy-3-(4,4,5,5-tetramethyl- l,3,2-dioxaborolan-2-yl)pyridine (895 mg, 3.81 mmol), Pd(dppf)C12 (414 mg, 0.51 mmol) and K2C03 (701 mg, 5.08 mmol) in dioxane (10 mL) and water (0.5 mL) was heated tol lO C and stirred overnight. The filtration removed the solid. After washing with DCM, the combined filtrate was concentrated in vacuo. The residue was purified by ISCO flash chromatography (eluted with 0-100% EtOAc / hexane) to provide 6-(4-methoxypyridin-3-yl)-lH-indazole. |
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