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CAS No. : | 159896-15-8 | MDL No. : | MFCD01075704 |
Formula : | C9H9BO4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | IEMLKNHGGSYOMP-ZZXKWVIFSA-N |
M.W : | 191.98 | Pubchem ID : | 5288001 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302 | 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 |
---|---|---|
With sodium hydrogencarbonate In methanol; water; N,N-dimethyl-formamide at 70℃; | 55 Example 55; (S)-2-[4'-(2-Carboxy-vinyl)-biphenyl-3-ylcarbamoyl]-pyrrolidine-l-carboxylic acid benzyl ester (Compound 6055)Using General Procedure J from 40.5 mg of 4-(2-Carboxy-vinyl)-phenylboronic acid. Yield 10.3 mg. MS: 446.1 (M+H+); H^NMR (DMSOd6): <5(ppm) 10.15 (s, IH), 7.99 (m, IH), 7.80 (m, 2H), 7.64-7.55 (m, 4H), 7.37-7.3 (m, 5H), 7.23 (m, IH), 7.07 (m, 2H), 6.59 (d, 2H5 J = 14.4 Hz), 5.1-4.9 (m, 2H), 4.39 (m, IH), 3.5 (m, 2H), 2.22 (m, IH), 1.92 (m, 3H). General Procedure J; A solution of (S)-2-(3-Bromo-phenylcarbamoyl)-pyrrolidine-l-carboxylic acid benzyl ester (100 mg, 0.25 mmol), aryl boronic acid (1 eq) described in the following Examples, Pd[P(Ph)3]4 (5 mol %, 14 mg) in methanol (2 mL), NaHCO3 (sat. aq., 300 uL) and DMF (400 uL) was degassed and heated to 70 0C overnight in a sealed vial. The reaction was cooled, filtered and the solvents removed. The resulting mixture was redissolved in 5 mL of 90% DMF, 10% water with .1 % TFA and purified by reverse phase HPLC to give the products. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With piperidine In pyridine malonic acid was added to soln. p-formylbenzeneboronic acid in pyridine at 25°C, piperidine was added and refluxed under N2 for 13 h; solvent was removed in vacuo, residue was taken up in water and acidified with concd. HCl, ppt. was collected, washed with water and dried in vacuo; elem. anal.; | |
80.73% | With pyridine In toluene for 2h; Reflux; | (E)-3-(4-Boronophenyl)acrylic acid (7) A mixture of (4-acetylphenyl)boronic acid(0.10 g, 0.67 mmol), malonate (0.21 g, 0.20 mmol) andpyridine (0.053 g, 0.67 mmol) in dry toluene (10 mL) was stirred at reflux for 2 h. After the reaction wascomplete as indicated by TLC, the mixture was cooled to room temperature and poured into water.The pH of the mixture was adjust to 5 by adding 10% aqueous hydrochloric acid solution and then itwas filtered to give intermediate 7 as a white solid (0.16 g, yield 80.73%). |
With piperidine In pyridine for 24h; Reflux; | Cinnamic Acid Derivatives 1; General Procedure General procedure: To a stirred solution of aldehyde (4.5 mmol) in pyridine (25 mL) wasadded malonic acid (10 mmol) and piperidine (4 mL). The resultingmixture was refluxed for 24 h. After cooling, the reaction mixture wasneutralized with aq 1 M HCl. White crystals formed were filtered andwashed with cold H2O. If necessary, carboxylic acids 1 can be ratherrecrystallized from aq EtOH or purified by column chromatographyon silica gel. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,2-dimethoxyethane; water at 85 - 100℃; Inert atmosphere; Sealed tube; | 5.3.1. General method for the preparation of compounds 9a-9i,9k-9q and 9s-9u General procedure: Step 1: Suzuki coupling. To a sealable vial containing 7(1.0 equiv) was added the corresponding boronic acid (1.1-1.5 equiv), Na2CO3 (5 equiv) and Pd(PPh3)4 (0.03-0.1 equiv). The mixture was diluted with either a mixture of DME/water (1:0.5-1.0), or a mixture of 1,4-dioxane/water (1:0.5-1.0) to a concentration of 0.015-0.074 M. The vial was flushed with N2, sealed, andheated to 85-100 °C. After 1.5-24 h of heating, the mixture was cooled to rt. The mixture was diluted with either satd NH4Cl, 1 N HCl, or water and extracted with CH2Cl2 or EtOAc. The combined organic layers were dried with sodium sulfate. The drying agent was removed by filtration and the filtrate was concentrated underreduced pressure. The residue was either used directly in the nextstep, or was purified by flash chromatography to afford theexpected cross-coupling product which was used in the next step. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: sodium carbonate; tetrakis(triphenylphosphine) palladium(0) / toluene; ethanol; water / 2 h / 80 °C / Inert atmosphere 2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine / dichloromethane / 4 h / 50 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In diethyl ether at 20℃; for 12h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate In 1,4-dioxane; water for 2h; Reflux; Inert atmosphere; | 4-(4-((4-Fluorophenyl)amino)pyrido[3,2-d]pyrimidin-6-yl)benzoic acid (5) General procedure: Amixture of 4 (0.21 g, 0.76 mmol), 4-phenylboronic acid (0.19 g, 1.5 mmol), bis(triphenylphosphine)palladium(II) chloride (0.028 g, 0.05 mmol) and potassium carbonate (0.32 g, 2.28 mmol) in 1,4-dioxaneand water (20 mL, V/V = 4:1) was refluxed for 2 h under aN2 atmosphere. After the reaction completionwas indicated by TLC, the mixture was cooled to room temperature and then poured to cooled water(20 mL). The pH of the mixture was adjusted to 5 using 10% aqueous hydrochloric acid solutionand then it was filtered and the solid was washed with dichloromethane and then dried to obtainintermediate 5 (0.26 g, yield 94.20%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: bis-triphenylphosphine-palladium(II) chloride; potassium carbonate / water; 1,4-dioxane / 2 h / Reflux; Inert atmosphere 2: sulfuric acid / 4 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: bis-triphenylphosphine-palladium(II) chloride; potassium carbonate / water; 1,4-dioxane / 2 h / Reflux; Inert atmosphere 2.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; dmap; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 0.5 h / 20 °C 2.2: 2 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: bis-triphenylphosphine-palladium(II) chloride; potassium carbonate / water; 1,4-dioxane / 2 h / Reflux; Inert atmosphere 2: sulfuric acid / 4 h / Reflux 3: sodium hydroxide; hydroxylamine / water; methanol / 0 - 20 °C / pH 11 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
22% | With tetrakis(triphenylphosphine) palladium(0) In water at 20 - 100℃; for 13h; Inert atmosphere; |
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