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CAS No. : | 14900-39-1 | MDL No. : | MFCD01074578 |
Formula : | C8H9BO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | YJCPVMYUISTDKG-UHFFFAOYSA-N |
M.W : | 147.97 | Pubchem ID : | 5003684 |
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 |
---|---|---|
83% | With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); at 120℃; for 3h; | To the triflate 46 (66.6 mg, 0.107 mmol) in toluene (2.8 ml)/ethanol (1.2 mL) /water (0.8 mL) was added potassium carbonate (37 mg, 0.268 mmol), trans-<strong>[14900-39-1]phenylvinylboronic acid</strong> (24.5 mg, 0.160 mmol) and tetrakis(triphenylphosphine)-palladium (0) (18.5 mg, 0.016 mmol). The mixture in the flask was flushed with argon three times and heated to 120C under argon for 3 hours. The mixture was cooled to room temperature, diluted with EtOAc and washed with 1N HCl, saturated NaHCO3] and brine. The organic phase was dried (MgSO4) and concentrated. The residue was chromatographed on a silica gel column, eluting with EtOAc/Hexane to afford the product 47 (51.4 mg, 83%). 1H NMR (CDCl3): delta 9.0 (d, 1H), 8.4 (d, 1H), 8.1 (s, 1H), 7.7 (d, 4H), 7.2-7.5 (m, 14H), 7.1 (d, 1H), 7.0 (dd, 2H), 6.8 (d, 1H), 4.8 (s, 2H), 4.4 (s, 2H). MS: 577 (M+1), 599 (M+23). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; water; toluene; at 120℃; for 3h;Heating / reflux; | To the triflate 5 (0.045 g, 0.07 mmol) in toluene (0.7 ml)/ethanol (0.3 mL) /water (0.2 mL) were added potassium carbonate (0.037 g, 0.175 mmol), trans-phenylvinylbronic acid (0.016 g, 0.105 mmol) and tetrakis (triphenylphosphine)-palladium (0) (0.012 g, 0.011 mmol). The mixture in the flask was flushed with argon three times. It was heated to 120C under argon for 3 hours. Cooling to room temperature, it was diluted with EtOAc and washed with 1N HCl, saturated NaHCO3 and brine. The organic phase was dried (MgSO4) and concentrated. The residue was chromatographed on a silica gel column, eluting with EtOAc/Hexane to afford the product 146 (0.031g, 75%). MS: 613 (M+Na). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With cesium fluoride;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water; at 75℃; for 7h; | (R, S)-N-trifluoroacetyl-7-methoxy-1-methyl-8-(1-phenyl-vinyl)-2, 3, 4,5-tetrahydro-1H-benzo[d]azepine A solution of (R,S)-N-trifluoroacetyl-8-bromo-7-methoxy-1-methyl-2,3,4,5-tetrahydro-1H- benzo [d] azepine. (8.19 mmol, 3.0 g) in dioxane: water (50 mL: 3 mL) was treated with cesium fluoride (24.6 mmol, 3.73 g) palladium tetrakistriphenylphosphine (0.82 mmol, 0.946 g) and 1-phenylvinyl boronic acid (16.4 mmol, 2.41 g). This was heated for 7 h at 75 C. The crude reaction was absorbed onto silica gel and concentrated. Flash chromatography (10% EtOAc in hexane, silica) resulted in 2. 28 g of yellow oil. MS calculated for C22H22F3NO2+H : 390, observed: 390. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With sodium hydrogencarbonate;bis-triphenylphosphine-palladium(II) chloride; In DMF (N,N-dimethyl-formamide); at 85℃; for 10h; | Step 1 2-Amino-4-styryl-thieno [2,3-d] pyrimidine-6-carboxylic acid ethyl ester To a solution of 2-amino-4-chloro-thieno [2, 3-d] pyrimidine-6-carboxylic acid ethyl ester (0. 193G, 0. 75MMOL.) and alpha-phenyl vinyl boronic acid (0. 17G, 1.5 equiv. ) in DMF at room temperature was added 1 M sodium hydrogen carbonate solution (1.88 ML, 2.5 equiv) followed by bis (triphenylphosphine) palladium (II) chloride (26mg, 0.05 equiv. ). Nitrogen was bubbled through the mixture for 5 minutes before heating to 85C and stirring for 10 hours. The cooled solution was partitioned between ethyl acetate and water, the combined organics washed with water and brine before being loaded directly on to an ISOLUTE SCX II ion exchange column. On elution with 1 M Ammonia in methanol and evaporation in vacuo, pure product was recovered as an orange powder (0. 169G, 70%) 'H NMR (CI3) 6 = 8.03 (1H, s); 8. 03 (1H, d, J = 15HZ) ; 7.59 (2H, m); 7.41- 7.30 (4H, m); 5.19 (2H, broad s) ; 4.31 (2H, q, J = 7. 1 Hz) and 1. 35 (3H, t, J = 7. 1 HZ). LCMS retention time 7.47 mins, [M+H] + = 326.12 (run time 15 minutes) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
17% | With trifluoroacetic acid;Pd(PPh3)4; In 1,2-dimethoxyethane; ethanol; water; toluene; | EXAMPLE 99 N-(1-methoxy-6-{3-[(E)-2-phenylethenyl]phenyl}-6H-benzo[c]chromen-8-yl)methanesulfonamide A solution of Example 82 (0.046 g, 0.1 mmol) in EtOH/DME/toluene (1 mL, 2:1:1) was added to <strong>[14900-39-1]phenylvinylboronic acid</strong> (0.015 g, 0.1 mmol). A solution of Pd(PPh3)4 (0.006 g, 0.005 mmol) in DME (0.5 mL) and aqueous Na2CO3 (20 mg in 0.3 mL H2O, 0.2 mmol) were added. The reaction mixture was heated to 90 C. on a shaker for 15 min then concentrated, diluted with DMSO/MeOH (1:1, 1 mL) and purified by HPLC with 0.1% TFA, water, and CH3CN to provide the titled compound (8 mg, 17%). 1H NMR (500 MHz, CDCL3) delta 8.46 (d, J=8.4 Hz, 1H), 7.50 (m, 4H), 7.36 (dd, J=15.3, 7.8 Hz, 3H), 7.26 (m, 3H), 7.17 (t, J=8.1 Hz, 1H), 7.09 (s, 2H), 6.72 (d, J=9.0 Hz, 1H), 6.65 (m, 2H), 6.24 (s, 1H), 6.01 (s, 1 H), 3.95 (s, 3H), 2.97 (s, 3H); MS (CI, +Q1MS) m/e 483. |
17% | With trifluoroacetic acid;Pd(PPh3)4; In 1,2-dimethoxyethane; ethanol; water; toluene; | EXAMPLE 99 N-(1-methoxy-6-{3-[(E)-2-phenylethenyl]phenyl}-6H-benzo[c]chromen-8-yl)methanesulfonamide A solution of Example 82 (0.046 g, 0.1 mmol) in EtOH/DME/toluene (1 mL, 2:1:1) was added to <strong>[14900-39-1]phenylvinylboronic acid</strong> (0.015 g, 0.1 mmol). A solution of Pd(PPh3)4 (0.006 g, 0.005 mmol) in DME (0.5 mL) and aqueous Na2CO3 (20 mg in 0.3 mL H2O, 0.2 mmol) were added. The reaction mixture was heated to 90 C. on a shaker for 15 min then concentrated, diluted with DMSO/MeOH (1:1, 1 mL) and purified by HPLC with 0.1% TFA, water, and CH3CN to provide the titled compound (8 mg, 17%). 1H NMR (500 MHz, CDCL3) delta 8.46 (d, J=8.4 Hz, 1H), 7.50 (m, 4H), 7.36 (dd, J=15.3, 7.8 Hz, 3H), 7.26 (m, 3H), 7.17 (t, J=8.1 Hz, 1H), 7.09 (s, 2H), 6.72 (d, J=9.0 Hz, 1H), 6.65 (m, 2H), 6.24 (s, 1H), 6.01 (s, 1H), 3.95 (s, 3H), 2.97 (s, 3H); MS (CI, +Q1MS) m/e 483. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
EXAMPLE 102A styrene alpha-boronic acid A solution of (x-bromo styrene (5.5 g, 30 mmol) in diethyl ether (30 mL) at -78 C. was treated with a solution of tert-BuLi (1.7 M solution, 21.2 mL, 36 mmol), stirred at -78 C. for 0.5 hours, treated with triisopropyl borate (8.31 mL, 36 mmol) over 48 minutes, stirred for 1 hour, warmed to room temperature over 18 hours, diluted with diethyl ether (100 mL), treated with 1M HCl (100 mL), stirred at room temperature for 5 hours, concentrated to remove the THF, adjusted pH 14 with 1N NaOH, washed with hexane, adjusted to pH 1 with 1M HCl, and extracted with ethyl acetate. The extract was dried (Na2SO4), filtered and concentrated to provide the title compound. 1H NMR (300 MHz, DMSO-d6) delta 5.75 (d, 1H), 5.83 (d, 1H), 7.2-7.39 (m, 5H, Ar-CH). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; at 80℃; for 18h; | A dioxane (8.0 mL)/water (2.0 mL) solution of 6-bromo-2-(4-methyl-thiazol-2-yl)- thieno[2,3-d]pyrimidin-4-ylamine (252 mg, 0.77 mmol), 1 -<strong>[14900-39-1]phenylvinylboronic acid</strong> (171 mg, 1.20 mmol), Pd(dppf)Cl2 (63 mg, 0.08 mmol), and K2CO3 (213 mg, 1.54 mmol) was heated to 80 0C. After 18 h the mixture was diluted with EtOAc and the solution was washed with water and brine, dried (Na2SO4), concentrated and purified via column chromatography to give 131 mg of the title compound. 1H NMR (Acetone ,400MHz): delta = 7.55 - 7.60 (m, 2 H), 7.50 - 7.55 (m, 3 H), 7.40 (s, 1 H), 7.35 (d, J=LO Hz, 1 H), 7.15 (br. s., 1 H), 5.80 (s, 1 H), 5.70 (s, 1 H), 2.55 ppm (d, J=LO Hz, 3 H); MS m/e 351 (M+H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydrogencarbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; at 100℃; for 3h; | A solution of 1 -tert-butyl-3,5-diiodo-2-methoxybenzene (4.94 g, 11.87 mmol) in dimethoxyethane (50 mL) and water (30 mL) was treated with 1 -<strong>[14900-39-1]phenylvinylboronic acid</strong> (2.283 g, 15.43 mmol), tetrakis(triphenylphosphine)palladium(0) (0.686 g, 0.593 mmol) and sodium bicarbonate (2.492 g, 29.7 mmol) followed by heating at 100 C for 3 hours. 1 N HCl was added and the mixture was extracted with ethyl acetate, then dried (Na2SO4), filtered and concentrated in vacuo to give crude product which was purified by silica gel flash chromatography eluting with 50: 1 hexanes/ethyl acetate to give the title compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium carbonate; In water; toluene; at 100℃; for 12h; | A mixture of 2,4,6-trichloropyrimidin-5-yl)methanol (1.1 g), 1 -<strong>[14900-39-1]phenylvinylboronic acid</strong> (0.8 g), Tetrakis (0.3 g), sodium carbonate (1.64 g) in toluene (14 mL) and water (3 mL) was heated at 100 0C for 12 h. Water was added followed by ethyl acetate, the aqueous layer was extracted with ethyl acetate (x3), and the combined organic layers were dried over anhydrous sodium sulfate and then filtered. The filtrate was concentrated, and the residue was purified Biotage eluting with 10-40% EtOAc/Hexanes to give the title compound as a white solid (325 mg). LC-MS (M+H)+ = 281.02. 1H NMR (500, MHz, chloroform-d) delta ppm 7.5 (5H, m), 6.01 (IH, s), 5.67 (IH, s), 4.62 (2H, s). | |
With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In water; toluene; at 100℃; for 12h; | Intermediate AN(1)2,4-dichloro-6-(l-phenylvinyl)pyrimidin-5-yl)methanolA mixture of 2,4,6-trichloropyrimidin-5-yl)methanol (1.1 g), 1 -<strong>[14900-39-1]phenylvinylboronic acid</strong> (0.8 g), Tetrakis (0.3 g), sodium carbonate (1.64 g) in toluene (14 mL) and water (3 mL) was heated at 100 C for 12 h. Water was added followed by ethyl acetate, the aqueous layer was extracted with ethyl acetate (x3), and the combined organic layers were dried over anhydrous sodium sulfate and then filtered. The filtrate was concentrated, and the residue was purified Biotage eluting with 10-40% EtOAc/Hexanes to give the title compound as a white solid (325 mg). LC-MS (M+H)+ = 281.02. XH NMR (500 MHz, chloroform-i/) delta ppm 7.5 (5H, m), 6.01 (1H, s), 5.67 (1H, s), 4.62 (2H, s). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63.9% | With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In toluene; at 90℃; for 16h;Inert atmosphere; | 30A. (S)-2-(1-(4-(1-phenylvinyl)phenyl)pyrrolidin-2-yl)acetonitrile To a solution of 1-<strong>[14900-39-1]phenylvinylboronic acid</strong> (120 mg, 0.811 mmol) and 20B (165 mg, 0.624 mmol) in toluene (0.9 mL) was added Na2CO3 (0.936 mL, 1.872 mmol), and Pd(Ph3P)4 (36.0 mg, 0.031 mmol). The reaction vessel was purged with argon, and the mixture was heated to 90 C. for 16 h. The reaction mixture was cooled to rt and was diluted with EtOAc. The organic layer was washed with water, then brine. The combined organic layers were dried and evaporated. Purification via silica gel chromatography gave 30A (clear oil, 115 mg, 0.399 mmol, 63.9% yield). LC-MS Anal. Calc'd for C20H20N2: 288.16. found [M+H] 289.0. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
26% | With sodium tetrachloroaurate(III) dihyrate; potassium carbonate; In ethanol; at 50℃; for 24h; | Representative experimental procedure: A mixture of AuCl (11.6 mg, 0.050 mmol), phenylboronic acid (1a, 121.9 mg, 1.00 mmol), K2CO3 (152.0 mg, 1.10 mmol) in EtOH (8.0 mL) was heated at 50 C under open air for 24 h. The reaction mixture was filtered through a plug of Florisil washing with hexane-AcOEt (3:1). The filtrate was concentrated under reduced pressure, and the resulting residue was subjected to preparative thin-layer chromatography (hexane:AcOEt = 20:1) to afford biphenyl (2a, 58.6 mg, 76%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With tris-(dibenzylideneacetone)dipalladium(0); copper(I) thiophene-2-carboxylate; trifuran-2-yl-phosphane; In tetrahydrofuran; at 55℃; for 0.5h;Inert atmosphere; | General procedure: All of the reactions started with 0.084 mmol (20.0 mg) of thiomethylbodipy 1 or, 0.068 mmol (20.0 mg) of diethyl thiomethylbodipy, as limiting reagent and the other components of the reaction were added in the amounts stated in the TP. An oven-dry Schlenk tube, equipped with a stir bar, was charged with the boronic acid (3 equiv), thiomethylbodipy 1 (1 equiv) and dry THF (2 mL) under N2. The stirred solution was sparged with N2 for 10 min, whereupon CuTC (3 equiv), Pd2(dba)3 (2.5 mol %), and TFP (7.5 mol %) were added under N2. The reaction mixture was immersed into a pre-heated oil bath at 55 C. After TLC showed that the reaction went to completion, the reaction mixture was allowed to reach room temperature and was adsorbed on SiO2-gel.CommentAfter flash-chromatography (SiO2-gel, EtOAc/hexanes gradient) purification, meso substituted BODIPYs were obtained as highly-colored crystalline solids or oils. For purposes of characterization, the solid products were crystallized from CH2Cl2/petroleum ether. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78.2% | With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate; In ethanol; water; toluene; for 15h;Inert atmosphere; Reflux; | Under an argon atmosphere, to a solution of 3-bromo-5-[4-(tert-butyldimethylsilyloxy)phenyl]pyrazin-2-amine (5) (1.00 g, 2.63 mmol) in toluene (30 mL) and ethanol (1.2 mL) were successively added 1-<strong>[14900-39-1]phenylvinylboronic acid</strong> (6c) (467 mg, 3.16 mmol), dichlorobis(triphenylphosphine)palladium (II) (110 mg, 157 mumol) and 1 M Na2CO3 aqueous solution (2.70 mL, 2.70 mmol) at room temperature, and the mixture was heated to reflux for 15 hours. After cooling to room temperature, to the mixture was added water and the metal catalyst was removed by filtration. The product was extracted with ethyl acetate (200 mL*3). The combined organic extract was washed successively with water (300 mL) and brine (300 mL), followed by drying over anhydrous sodium sulfate. After filtration and concentration under reduced pressure, the residue was purified by column chromatography (silica gel 100 g, n-hexane/ethyl acetate=3/1) to give Compound 7c (830 mg, 2.06 mmol, 78.2%) as a brown oily substance. Rf=0.33 (n-hexane/diethyl ether=2/3); 1H NMR (400 MHz, DMSO-d6) delta 0.15 (s, 6H), 0.91 (s, 9H), 5.50 (s, 1H), 5.93 (s, 2H), 5.97 (s, 1H), 6.80-6.87 (AA'BB', 2H), 7.26-7.36 (m, 5H), 7.71-7.77 (AA'BB', 2H), 8.45 (s, 1H); 13C NMR (75.5 MHz, DMSO-d6) delta -4.6 (2C), 17.9, 25.5 (3C), 117.9, 120.0 (2C), 126.3 (2C), 126.5 (2C), 128.0, 128.4 (2C), 130.5, 137.7, 138.2, 139.0, 139.2, 144.4, 151.8, 154.9; IR (KBr, cm-1) 517, 552, 608, 629, 677, 692, 708, 779, 806, 843, 910, 1009, 1026, 1063, 1105, 1148, 1169, 1202, 1263, 1323, 1362, 1389, 1423, 1449, 1510, 1605, 2857, 2886, 2928, 2953, 3034, 3055, 3175, 3298, 3387, 3481. |
With sodium carbonate;dichlorobis(triphenylphosphine)palladium[II]; In ethanol; water; toluene; | 2-3) TMD-347 (4c) 5-[4-(tert-Butyldimethylsilyloxy)phenyl]-3-(1-phenylvinyl)pyrazin-2-amine (7c) Under an argon atmosphere, to a solution of 3-bromo-5-[4-(tert-butyldimethylsilyloxy)phenyl]pyrazin-2-amine (5) (1.00 g, 2.63 mmol) in toluene (30 mL) and ethanol (1.2 mL) were successively added 1-<strong>[14900-39-1]phenylvinylboronic acid</strong> (6c) (467 mg, 3.16 mmol), dichlorobis(triphenylphosphine)palladium (II) (110 mg, 157 mumol) and 1 M Na2CO3 aqueous solution (2.70 mL, 2.70 mmol) at room temperature, and the mixture was heated to reflux for 15 hours. After cooling to room temperature, to the mixture was added water and the metal catalyst was removed by filtration. The product was extracted with ethyl acetate (200 mL*3). The combined organic extract was washed successively with water (300 mL) and brine (300 mL), followed by drying over anhydrous sodium sulfate. After filtration and concentration under reduced pressure, the residue was purified by column chromatography (silica gel 100 g, n-hexane/ethyl acetate=3/1) to give Compound 7c (830 mg, 2.06 mmol, 78.2%) as a brown oily substance. Rf=0.33 (n-hexane/diethyl ether=2/3); 1H NMR (400 MHz, DMSO-d6) delta 0.15 (s, 6H), 0.91 (s, 9H), 5.50 (s, 1H), 5.93 (s, 2H), 5.97 (s, 1H), 6.80-6.87 (AA'BB', 2H), 7.26-7.36 (m, 5H), 7.71-7.77 (AA'BB', 2H), 8.45 (s, 1H); 13C NMR (75.5 MHz, DMSO-d6) delta -4.6 (2C), 17.9, 25.5 (3C), 117.9, 120.0 (2C), 126.3 (2C), 126.5 (2C), 128.0, 128.4 (2C), 130.5, 137.7, 138.2, 139.0, 139.2, 144.4, 151.8, 154.9; IR (KBr, cm-1) 517, 552, 608, 629, 677, 692, 708, 779, 806, 843, 910, 1009, 1026, 1063, 1105, 1148, 1169, 1202, 1263, 1323, 1362, 1389, 1423, 1449, 1510, 1605, 2857, 2886, 2928, 2953, 3034, 3055, 3175, 3298, 3387, 3481. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
66.8% | With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In ethanol; water; benzene; at 80℃; for 120h;Inert atmosphere; | General procedure: N, N'-bis (2,6-diisopropylphenyl) -1,7-dibromoperylene-3,4,9,10-tetracarboxydiimide(1.0 g, 1.15 mmol) dried ethanol (5.79 ml),Benzene (33.12 ml),After dissolving in water (8.13 ml) co-solvent1-phenyl vinyl boronic acid (0.68 g, 4.6 mmol),Pd (PPh3) 4 (66.57 mg, 5.0 mol%),Na2CO3 (1.2 g, 11.5 mmol) was added sequentially under nitrogen gas. After reacting at 80 C. for 120 hours, water was added to quench and extracted several times with CH 2 Cl 2.The extracted organic layer was dried several times over MgSO4, and then evaporated under reduced pressure to remove the solvent.The obtained crude solid was purified by column chromatography on silica gel with 100% CH2Cl2.The product was obtained by receiving a second band containing a yellow compound.The resulting compound was diphenylcoronene tetracarboxydiimide (Cd1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
55% | With potassium phosphate;dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II); In tetrahydrofuran; water; at 50℃; for 4h;Inert atmosphere; sealed tube; | In a 5 mL microwave tube was added Example 18P (120 mg, 0.158 mmol), 1- <strong>[14900-39-1]phenylvinylboronic acid</strong> (40 mg, 0.237 mmol), l,l'-bis(di-?eri-butylphosphino)ferrocene palladium dichloride (5.13 mg, 7.88 muiotaetaomicron) and potassium phosphate (66.9 mg, 0.315 mmol) in tetrahydrofuran (1.5 mL) and water (0.5 mL). The mixture was sparged with nitrogen for 5 minutes; the vessel was sealed and heated at 50 C for 4 hours. The mixture was cooled and partitioned with ethyl acetate and water. The organic layer was washed with brine, dried with sodium sulfate, filtered and concentrated. The residue was purified by chromatography on a 12 g silica cartridge eluting with 1-3% methanol in dichloromethane to give the title compound (49 mg, 55%). .H NMR (400 MHz, DMSO-i¾) delta ppm 0.51 - 0.59 (m, 1 H) 0.78 - 0.87 (m, 7 H) 0.96 - 1.02 (m, 2 H) 1.23 - 1.32 (m, 1 H) 1.34 - 1.45 (m, 1 H) 1.56 - 1.68 (m, 1 H) 2.37 - 2.43 (m, 1 H) 3.14 (s, 3 H) 3.60 - 3.69 (m, 1 H) 3.70 - 3.80 (m, 1 H) 5.53 (s, 1 H) 5.61 (s, 1 H) 7.05 (s, 1 H) 7.19 (s, 1 H) 7.29 - 7.45 (m, 8 H) 7.88 (s, 1 H) 7.92 (d, J=8.46 Hz, 2 H) 12.44 (s, 1 H); MS (ESI+) m/z 566 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With tris-(dibenzylideneacetone)dipalladium(0); 1,6-bis(diphenylphosphino)hexane; silver carbonate; In tetrahydrofuran; at 40℃; for 24h;Sealed tube; Inert atmosphere; | General procedure: Preparation of catalyst solution. In a glovebox, to a 20 mL vial charged with dpph (136.4 mg, 0.30 mmol) and Pd2dba3 (68.7 mg, 0.075 mmol) was added THF (7.5 mL). The solution was stirred at 23 C for 30 min. The freshly prepared catalyst solution was used in the following reactions: in a glovebox, to a 7 mL vial with stir bar, charged with MIDA boronate 2 (26.2 mg, 0.1 mmol) was added Ag2CO3 (110.0 mg, 0.4 mmol). Boronic acid (0.15 mmol) was added, followed by THF (0.50 mL). An aliquot of the prepared catalyst solution (0.50 mL) was added in one portion. The vial was sealed with a septum cap and removed from the glovebox. The solution was stirred at 40 C for 24 h. The reaction mixture was filtered through a pad of Celite, concentrated in vacuo, and analyzed by 1H NMR. Select samples were dry loaded onto Celite from an acetone solution, and purified via flash chromatography on silica (Et2O/MeCN 100:0/80:20) to afford the MIDA boronate 8. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
370 mg | With bis-triphenylphosphine-palladium(II) chloride; water; sodium carbonate; In ethanol; acetonitrile; at 130℃; for 0.75h;Microwave irradiation; | Example 116: 4,5-Dihydroxy-2-(l-phenylvinyl)isophthalonitrile The title compound was prepared from 4-bromo-3,5-dicyano- 1 ,2-phenylene diacetate (500 mg) and l-<strong>[14900-39-1]phenylvinylboronic acid</strong> (321 mg) instead of 3,4,5-trifluorophenylboronic acid as described in Example 7. Reaction conditions: 45 min at 130 C. Yield 370 mg NMR (400 MHz, DMSO-d6) ppm 7.32-7.40 (m, 4 H) 7.24-7.28 (m, 2 H) 6.17 (s, 1 H) 5.44 (s, 1 H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
49% | With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In toluene; at 90℃; for 4h;Inert atmosphere; | General procedure: mixture of 1-phenylvinylboronic acid (1 g, 6.75 mmol, 1.25 eq.), <strong>[15540-81-5]4-bromo-2,5-dimethylnitrobenzene</strong> (1.24 g, 5.4 mmol, 1 eq.) and tetrakis(triphenylposphine)palladium (0.32 g, 0.28 mmol, 0.05 eq.) in toluene (10 mL) and 2M sodium carbonate (8 mL) was stirred under argon at 90C for 4 hours. After completion, the mixture was filtered, diluted with water and extracted with ethyl acetate. The combined organic phases were washed with brine solution, dried over anhydrous sodium sulfate and the solvent was removed under reduced pressure. Purification by column chromatography (ethyl acetate/c-hexane) afforded the title compound (917 mg, 49% yield). |
Tags: 14900-39-1 synthesis path| 14900-39-1 SDS| 14900-39-1 COA| 14900-39-1 purity| 14900-39-1 application| 14900-39-1 NMR| 14900-39-1 COA| 14900-39-1 structure
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