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CAS No. : | 843662-48-6 | MDL No. : | N/A |
Formula : | C9H9BO4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | QCHIEOGZUMAQKI-SNAWJCMRSA-N |
M.W : | 191.98 | Pubchem ID : | 5844876 |
Synonyms : |
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P301+P312-P302+P352-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-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 |
---|---|---|
With potassium carbonate In 1,2-dimethoxyethane; ethanol; water at 87℃; for 8h; | B289.1 B289. 1: 5-Chloro-2-(3-(2-carboxyetheneyl)phenyl)-N-(2-aminoethyl)-8-methyl-8H- imidazo[4, 5-DLTHIAZOLOR5, 4-BLPYRIDINE A solution of B99.3 (0.5 g, 1.65 mmol), (E)-3- (3-BORONOPHENYL) acrylic acid (0.473 g, 2.475 mmol), PD (PH3P) 4 (0. 095 g, 0.0825 mmol), and 2M aq. K2C03 (1.65 mL) in DME (10 ML) and ETOH (4 mL) was heated to 87°C for 8 h. Upon cooling, the product was filtered and washed with ETOH, then the product was recrystallized from THF to afford B289. 1 (0.275 g) as a light yellow solid. HPLC retention time 3.30 min. Column : Chromolith SpeedROD 4. 6X50 mm (4 min grad. 0% B-100% B) Solvent A: 10% MeOH-90% H20 0.2% phosphoric acid Solvent B: 90% MeOH-10% H20-0.2% phosphoric acid. MS (ES): M/Z 371.06, 373.06 [M+H] |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
39% | With sodium carbonate In 1,2-dimethoxyethane; water for 3h; Heating / reflux; | 59.1 To a round-bottomed flask were added 4- [ (4-BROMOPHENYL) (3,3, 5,5- tetramethylcyclohexylidene) methyl] phenol (14 (85% pure-contains 15% 3, 3,5, 5- TETRAMETHYLCYCLOHEXANONE) (0.117 g, 0.25 mmoL), 3-(2-carboxyvinyl) benzeneboronic acid (0.117 g, 0.61 mmoL), tetrakis (TRIPHENYLPHOSPHINE) PALLADIUM (0) (0.026 g, 0.022 mmoL), 2 M NA2CO3 (3 mL), and ethylene glycol dimethyl ether (8 mL). The stirred reaction mixture was heated at reflux under a nitrogen atmosphere for 3 h. The oil bath was removed and the reaction mixture was allowed to cool at RT. The reaction mixture was transferred to a separatory funnel and partitioned between H2O and EtOAc. The organic phase was separated, dried (MGS04), filtered, and the filtrate was CONCENTRATED IN VACUO to give an oil. The crude product was purified by reverse phase preparative HPLC on a C-18 column with a CH3CN : H20 gradient (75: 25 to 100: 0) and 0.05% TFA as a modifier to give 0.046 g (39%) of compound 164 as an off-white SOLID. H NMR (400 MHz, DMSO-D6) : 8 0.89 (s, 12 H), 1.26 (s, 2 H), 1.93 (s, 4 H), 6.63 (d, J = 16. 2 HZ, 1 H), 6.67 (d, J = 8. 4 HZ, 2 H), 6.95 (d, J = 8. 5 Hz, 2 H), 7.20 (d, J = 8. 2 HZ, 2 H), 7.46 (t, J = 7. 7 HZ, 1 H), 7.65 (m, 5 H), 7.95 (s, 1 H), 9.27 (s, 1 H), 12. 39 (br s, 1 H). Anal. CALCD for C32H3403. 0.25 H20 : C, 81.58 ; H, 7.38. Found: C, 81.62 ; H, 7.33. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
tris-(dibenzylideneacetone)dipalladium(0); | Example 174 (2E)-3-[3-(2-[4-(2,3-dihydro-1-benzofuran-5-yl)-4-oxobutanoyl]amino}-6-phenylpyridin-4-yl)phenyl]acrylic acid Using N-(4-chloro-6-phenylpyridin-2-yl)-4-(2,3-dihydro-1-benzofuran-5-yl)-4-oxobutanamide obtained in Example 114-(1) (20.3 mg), tris(dibenzylideneacetone)dipalladium (1.1 mg), biphenyl-2-yl(dicyclohexyl)phosphine (1.8 mg), 1N aqueous potassium carbonate solution (0.1 mL) and (2E)-3-[3-(dihydroxyboryl)phenyl]acrylic acid (24.0 mg) as starting materials and in the same manner as in Example 119, (2E)-3-[3-(2-[4-(2,3-dihydro-1-benzofuran-5-yl)-4-oxobutanoyl]amino}-6-phenylpyridin-4-yl)phenyl]acrylic acid (4.4 mg) was obtained. HPLC (220 nm) purity 96% (retention time 1.91 min) MS (ESI+, m/e) 519 (M+H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
12% | With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In N,N-dimethyl-formamide at 100℃; for 0.166667h; Microwave irradiation; | |
12% | With sodium carbonate In N,N-dimethyl-formamide at 100℃; for 0.166667h; Sealed tube; Microwave irradiation; | 3 Example 3; Preparation of compound 36; (E)-3-[3-[6-(4-Methyl-[1,4]diazepan-1-yl)-pyridin-2-yl]-phenyl]-acrylic acid 2,6-Dichloropyridine (200 mg, 1.35 mmol) was dissolved in 5 mL DMF. N-methylhomopiperazine (500 μL, 4.02 mmol) was added and the resulting mixture was heated at 105° C. for 16 hours. The reaction mixture was concentrated, loaded onto a flash column and eluted with a methanol/dichloromethane gradient. Intermediate D was isolated by evaporation of the solvent and used directly (160 mg, 53%). 3-(E-2-carboxyvinyl)benzeneboronic acid (50 mg, 0.26 mmol) and bistriphenylphosphinepalladium(II)chloride (10 mg, 0.01 mmol) were combined in a microwave reaction tube. Intermediate D prepared above (55 mg, 0.24 mmol) was added as a solution 3 mL DMF, and 1 mL of 2M Na2CO3 was then added. The tube was sealed and the reaction mixture was heated in a microwave reactor for 10 minutes at 100° C. The reaction mixture was then filtered through a plug of celite and purified directly by preparative HPLC. The product was further purified by preparative TLC to provide the title compound as a white solid (10 mg, 12%); MS analysis electrospray, 338 (M+H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In N,N-dimethyl-formamide at 100 - 150℃; Microwave irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: 3-[(E)-2-carboxyvinyl]benzeneboronic acid; 1-(6-chloropyrazin-2-yl)perhydro-1,4-diazepine With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In N,N-dimethyl-formamide at 100 - 150℃; Microwave irradiation; Stage #2: trifluoroacetic acid In water; acetonitrile |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In N,N-dimethyl-formamide at 100 - 150℃; Microwave irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In N,N-dimethyl-formamide at 100 - 150℃; Microwave irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In N,N-dimethyl-formamide at 100 - 150℃; Microwave irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: 3-[(E)-2-carboxyvinyl]benzeneboronic acid; N(1)-(6-chloropyrazin-2-yl)propane-1,3-diamine With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In N,N-dimethyl-formamide at 100 - 150℃; Microwave irradiation; Stage #2: trifluoroacetic acid In water; acetonitrile |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In N,N-dimethyl-formamide at 100 - 150℃; Microwave irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In N,N-dimethyl-formamide at 100 - 150℃; Microwave irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In N,N-dimethyl-formamide at 100 - 150℃; Microwave irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In N,N-dimethyl-formamide at 100 - 150℃; Microwave irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In N,N-dimethyl-formamide at 100 - 150℃; Microwave irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In N,N-dimethyl-formamide at 100 - 150℃; Microwave irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In N,N-dimethyl-formamide at 100 - 150℃; Microwave irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
12% | With sodium carbonate In N,N-dimethyl-formamide at 100℃; for 0.166667h; Sealed tube; Microwave irradiation; | 1 Example 1; Preparation of compound 1; (E)-3-{3-[6-(4-Amino-cyclohexylamino)-pyrazin-2-yl]-phenyl}-acrylic acid 2,6-Dichloropyrazine (100 mg, 0.67 mmol) was dissolved in 1 mL dichloromethane. Trans-1,4-cyclohexanediamine (137 mg, 1.2 mmol) was added and the resulting mixture was agitated for 72 hours. The reaction mixture was directly loaded onto a flash column and eluted with an ammonium hydroxide/methanol/dichloromethane gradient. The intermediate A (17 mg, 11%) was isolated by evaporation of the solvent and used directly. 3-(E-2-carboxyvinyl)benzeneboronic acid (25 mg, 0.13 mmol) and bistriphenylphosphinepalladium(II)chloride (10 mg, 0.01 mmol) were combined in a microwave reaction tube. Intermediate A prepared above (17 mg, 0.07 mmol) was added as a solution in 3 mL DMF, and 1 mL of 2M Na2CO3 was then added. The tube was sealed and the reaction mixture was heated in a microwave reactor for 10 minutes at 100° C. The reaction mixture was then filtered through a plug of celite and purified directly by preparative HPLC. The title compound was collected as a white solid (3 mg, 12%) following evaporation of the solvent; MS analysis electrospray, 339 (M+H). |
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In N,N-dimethyl-formamide at 100 - 150℃; Microwave irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In N,N-dimethyl-formamide at 100 - 150℃; Microwave irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
35% | With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In N,N-dimethyl-formamide at 100 - 150℃; Microwave irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In N,N-dimethyl-formamide at 100 - 150℃; Microwave irradiation; | ||
With sodium carbonate In N,N-dimethyl-formamide at 100℃; for 0.166667h; Sealed tube; Microwave irradiation; | 2 Example 2; Preparation of compound 2 (E)-3-{3-[6-(4-Amino-cyclohexylamino)-pyrazin-2-yl]-phenyl}-acrylic acid 2,6-Dichloropyrazine (100 mg, 0.67 mmol) was dissolved in 2 mL DMF. Cis-(4-Amino-cyclohexyl)-carbamic acid tent-butyl ester (257 mg, 1.2 mmol) was added and the resulting mixture was heated at 45° C. with agitation for 24 hours. The reaction mixture was concentrated and purified by preparative TLC using a methanol/dichloromethane eluant. Intermediate B (90 mg, 41%) was isolated by evaporation of the solvent and was used directly. 3-(E-2-carboxyvinyl)benzeneboronic acid (55 mg, 0.28 mmol) and bistriphenylphosphinepalladium(II)chloride (15 mg, 0.015 mmol) were combined in a microwave reaction tube. Intermediate B prepared above (90 mg, 0.27 mmol) was added as a solution in 3 mL DMF, and 1 mL of 2M Na2CO3 was then added. The tube was sealed and the reaction mixture was heated in a microwave reactor for 10 minutes at 100° C. The reaction mixture was then filtered through a plug of celite and purified directly using preparative TLC with a methanol/ammonium hydroxide/dichloromethane eluant. The intermediate was isolated by evaporation of the solvent and taken up in 5 mL of a 20% TFA/dichloromethane solution. After stirring at room temperature overnight, the mixture was concentrated and purified by preparative HPLC. The title compound was collected as a yellow solid (85 mg, 91%) following evaporation of the solvent; MS analysis electrospray, 339 (M+H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In N,N-dimethyl-formamide at 100 - 150℃; Microwave irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In N,N-dimethyl-formamide at 100 - 150℃; Microwave irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate In ethanol; toluene at 80℃; for 4h; Inert atmosphere of nitrogen; | 3-1.A Under nitrogen atmosphere, (R)-2-bromo-N-(2-hydroxy-3-(2-methyl-1-naphthalen-2-yl)propan-2-ylamino)propyl)-N-methylbenzenesulfonamide (Exp. 2-1, 25.4 mg) was dissolved in toluene (2 mL), potassium carbonate (WAKO, 22.8 mg), 3-(2-carboxyvinyl)benzeneboronic acid (ba13, LANC, 15.8 mg), bis1,1'-bis(diphenylphosphinoferrocene)palladium(II) dichloride-dichloromethane complex (Ald, 9 mg) and ethanol (1 mL) were added thereto followed by stirring at 80° C. for four hours. The reaction solution was charged in a diatomaceous earth column, and then eluted with chloroform and ethyl acetate. The solvent was distilled off under reduced pressure. The residue was used for the next Step B. without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
32% | With sodium carbonate In N,N-dimethyl-formamide at 100℃; for 0.166667h; Sealed tube; Microwave irradiation; | 4 Example 4; Preparation of compound 25; (E)-3-{3-[6-(4-Amino-piperidin-1-yl)-pyrazin-2-yl]-phenyl}-acrylic acid 2,6-Dichloropyrazine (100 mg, 0.67 mmol) was dissolved in 1 mL dichloromethane. Piperidin-4-yl-carbamic acid tent-butyl ester (240 mg, 1.2 mmol) was added and the resulting mixture was agitated at room temperature for 72 hours. The reaction mixture was loaded directly onto a flash column and eluted with an ethyl acetate/hexane gradient. Intermediate E (108 mg, 52% yield) was isolated by evaporation of the solvents. [3-(E-3-methoxy-3-oxo-1-propen-1-yl)phenyl]boronic acid (80 mg, 0.41 mmol) and bistriphenylphosphinepalladium(II)chloride (20 mg, 0.02 mmol) were combined in a microwave reaction tube. Intermediate E prepared above (104 mg, 0.33 mmol) was added as a solution in 3 mL DMF, and 1 mL of 2M Na2CO3 was then added. The tube was sealed and the reaction mixture was heated in a microwave reactor for 10 minutes at 100° C. The reaction mixture was then filtered through a plug of celite, and the solvents were concentrated to provide 45 mg (32% yield) of intermediate F which was used directly. Intermediate F (40 mg, 0.09 mmol) was dissolved in methanol and treated with 1 mL of 4N HCl in dioxane. After stirring the mixture for 16 hours at room temperature, the solvents were evaporated to provide the esterified product G which was subsequently taken up in 2 mL acetonitrile, and treated with 1 mL of 1N NaOH. The resulting mixture was stirred at room temperature for 4 hours then concentrated. The residue was purified by preparative HPLC, then further purified by preparative TLC. The title compound (13 mg, 43%-2 steps) was isolated following evaporation of the solvent; MS analysis electrospray, 325 (M+H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With tris-(dibenzylideneacetone)dipalladium(0); sodium carbonate; XPhos In water; acetonitrile at 90℃; for 1.5h; Inert atmosphere; | A stirred suspension of 5-bromo-1H-pyrrolo[2,3-b]pyridine (150 mg, 0.76 mmoles), 2-(Dicyclohexylphosphino)-2',4',6'-tri-i-propyl-1,1'-biphenyl (109 mg, 0.23 mmoles), Tris(dibenzylideneacetone)dipalladium (0) (70 mg, 0.08 mmoles), Sodium carbonate (121 mg, 1.14 mmoles), and 3-(2-carboxyvinyl)benzeneboronic acid (219 mg, 1.14 mmoles) in acetonitrile (4 mL) and water (1 mL). This was placed under an atmosphere of nitrogen and warmed to 90 °C for about 90 min. Aqueous workup was performed using methylene chloride. The organic phases were combined, washed with brine,dried over sodium sulfate, and concentrated in vacuo. Reverse-phase chromatography (water, acetonitrile, formic acid additive) was used for purification, and it was characterized by HPLC (UV, 254 nm) and proton NMR). |
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