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CAS No. : | 4433-63-0 | MDL No. : | MFCD01074536 |
Formula : | C2H7BO2 | Boiling Point : | - |
Linear Structure Formula : | CH3CH2B(OH)2 | InChI Key : | PAVZHTXVORCEHP-UHFFFAOYSA-N |
M.W : | 73.89 | Pubchem ID : | 521157 |
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: |
* 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 |
---|---|---|
2 g | With potassium phosphate; palladium diacetate; tricyclohexylphosphine; In water; toluene;Reflux; Inert atmosphere; | To a mixture of 4-bromo-3-methoxy-benzaldeyde (5.0 g, 23.38 mmol), ethylboronic acid (5.2 g, 71 mmol) and potassium phosphate (17.3 g, 81.83 mmol) in toluene (100 mL) was added water (10 mL), tricyclohexylphosphine (0.65 g, 2.33 mmol) and palladium (II) acetate (260 mg, 1.16 mmol). The reaction mixture was heated at reflux under argon atmosphere overnight. The reaction was cooled, and then diluted with ethyl acetate. The organic layer was washed with water and brine, and then dried over anhydrous sodium sulfate and then concentrated in vacuo. The residue was purified by column chromatography to give 4-ethyl-3-methoxy-benzaldehyde (2 g). |
2 g | With potassium phosphate; palladium diacetate; tricyclohexylphosphine; In water; toluene;Inert atmosphere; Reflux; | Step 1: Preparation of 4-ethyl-3-methoxy-benzaldehyde To a mixture of 4-bromo-3-methoxy-benzalcleyde (5.0 g, 23.38 mmol), ethylboronic acid (5.2 g.71 mmol) and potassium phosphate (17.3 g, 81.83 mmol) in toluene ( 100 ml.) was added water ( 10 mL), tricyclohexylphosphinc (0.65 g, 2.33 mmol) and palladium (II) acetate (260 mg, 1.16 mmol). The reaction mixture was heated at reflux under argon atmosphere overnight. The reaction was cooled, and then diluted with ethyl acetate. The organic layer was washed with water and brine, and then dried over anhydrous sodium sulfate and then concentrated in vacuo. The residue was purified by column chromatography to give 4-ethyl-3-methoxy-benzaldehydc (2 g). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
39% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,4-dioxane; at 140℃; for 16h; | Pyridyl amine 9: Step 1: A mixture of <strong>[136888-21-6]2-chloro-5-fluoro-3-nitropyridine</strong> (2 g, 11.33 mmol) and ethylboronic acid (1.674 g, 22.66 mmol) in Dioxane (Volume: 28.3 ml) was treated with potassium carbonate (6.26 g, 45.3 mmol) and Pd(Ph3P)4 (0.393 g, 0.340 mmol). The mixture was heated at 140 C for 16 h, cooled to rt, and then, filtered through celite with ethyl acetate. The concentrated filtrate was purified by chromatography (hexanes to 10:90 EA/Hex) to afford the product in 39% yield (750 mg, 4.41 mmol). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
48% | With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate; In 1,4-dioxane; water; at 100℃; for 6h;Inert atmosphere; | A mixture of <strong>[99365-48-7]4-bromoindolin-2-one</strong> (500 mg, 2.36 mmol), ethylboronic acid (523 mg, 7.07 mmol), Pd(dppf)Cl2 (345 mg, 0.472 mmol) and Na2C03 (750mg, 7.07 mmol) in dioxane (10 mL) and water (2 mL) was degassed and purged with N2 for 3 times. And the resulting reaction mixture was stirred at 100 C for 6 hours under N2 atmosphere. A black suspension was formed. LCMS showed the purity of the desired product is 43% (Rt = 0.603 min; MS Calcd: 161.1; MS Found: 161.9 [M+H]+). The reaction mixture was filtered through a pad of celite and the solid was washed with EtOAc (100 mL). The aqueous layer was extracted with EtOAc (30 mL x2). The filtrate was washed with water (40 mL x2), brine (40 mL), dried over anhydrous Na2S04, filtered and concentrated under reduced pressure. The residue was purified by Combi Flash (20% to 50% EtOAc in PE) to give 4-ethylindolin-2-one (220 mg, yield: 48%) as a yellow solid. NMR (400 MHz, CDCb) d 1.22 (3H, t , J= 7.6 Hz), 2.59 (2H, q, J= 7.6 Hz), 3.47 (2H, s), 6.73 (1H, d , J= 7.8 Hz), 6.88 (1H, d, J= 7.8 Hz), 7.13-7.19 (1H, m), 8.31 (1H, brs). |