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CAS No. : | 6783-05-7 | MDL No. : | MFCD00963621 |
Formula : | C8H9BO2 | Boiling Point : | - |
Linear Structure Formula : | (HO)2BCHCHC6H5 | InChI Key : | VKIJXFIYBAYHOE-VOTSOKGWSA-N |
M.W : | 147.97 | Pubchem ID : | 5702628 |
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 |
---|---|---|
47% | With sodium carbonate;(1,1'-bis(diphenylphosphine)ferrocene)palladium(0); In DMF (N,N-dimethyl-formamide); water; toluene; at 80℃; for 20h; | A mixture of (E)-2- PHENYLETHENYLBORONIC acid (0.93 g, 6.2 MMOL), 4-CHLORO-5-IODOPYRIMIDINE (1.5 g, 6.2 MMOL), 2M sodium carbonate solution (1.5 mL) and 1,1'- bis (DIPHENYLPHOSPHINO) ferrocene PALLADIUM (II) (0.39 g) in dimethylformamide : toluene 1: 2 (15 mL) was heated at 80C for 20 h. The reaction mixture was partitioned between DICHLOROMETHANE and water. The DICHLOROMETHANE layer was dried, concentrated, and chromatographed on silica gel, eluting with ethyl acetate: hexane 1: 9 to give the title compound (0.61 g, 47%). 1H NMR (400 MHz; DMSO-d6) O 7.22 (d, J=16 Hz, 1H), 7.33-7. 42 (m, 3H), 7.54 (d, J=16 Hz, 1H), 7.63 (d, J=8 Hz, 2H), 8.89 (s, 1H), 9.22 (s, 1H) ; ESIMS : 217 (M+H) + |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water; at 100℃; | To a hot (100 0C) solution of intermediate A.ii (18.5 g, 81.8 mmol), K2CO3 (14.7 g, 106 mmol), trans-2-phenylboronic acid (13.7 g, 90 mmol) in dioxane (320 mL) and water (80 mL) was added Pd(PPh3 )4 (4.77 g, 5 mol%). The resulting mixture was stirred at 1000C over night. After cooling, the reaction mixture was diluted with water (300 mL). The volatiles were removed in vacuo and the residue was taken up in EA (300 mL). The two layers were separated and the aq. layer was extracted one more with EA (300 mL). The combined org. layers were washed with brine, dried over MgSO4, filtered and <n="39"/>concentrated to dryness. The residue was chromatographed (EA-Hept 1 :2) to afford the title compound as a yellow solid (17.79 g, 87% yield).1H NMR (CDCl3) delta: 8.89 (d, J = 4.6 Hz, IH); 8.16 (dd, J = 9.5, 5.5 Hz, IH); 7.83 (dd, J = 2.7, 9.5 Hz, IH); 7.70-7.63 (m, 4H); 7.55-7.34 (m, 5H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | With tetraethylammonium hydroxide;tetrakis(triphenylphosphine) palladium(0); In N,N'-dimethylacetamide (DMA); at 110℃; for 24h; | 1b) 2,8-Bis-((E)-styryl)-dibenzofuran Tetrethylamine hydroxide (13.6 g, 18.4 mmol), tetrakis(triphenylphosphine)palladium(0) (142 mg) and trans-2-phenylvinylboronic acid (2.3 g, 15.3 mmol) are added to a solution of the product from example 1a) (2.00 g, 6.14 mmol) in N,N'-Dimethylacetamide (DMA) (30 ml). The mixture is then stirred at 110° C. for 24 hours. The reaction mixture is cooled to room temperature and poured into H2O. A gray crude product is obtained after filtration and washing with n-hexane. The crude product is purified by silicagel column chromatography with CH2Cl2, which result in a white solid (71percent yield, mp.: 226° C.). 1H-NMR (CDCl3, ppm): 7.26-7.30 (m, 6H), 7.39 (t, 4H), 7.54-7.58 (m, 6H), 7.65 (dd, 2H), 8.12 (d, 2H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With potassium carbonate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In dimethyl sulfoxide; at 95℃; for 16h; | a) (E)-2-Methoxy-4-styrylpyrimidine A solution of <strong>[51421-99-9]4-chloro-2-methoxypyrimidine</strong> (0.36 g, 2.5 mmol), trans-2-phenylvinylboronic acid (0.56 g, 3.8 mmol) and potassium carbonate (0.69 g, 5.0 mmol) in DMSO (8.0 mL) was purged with argon for 5 min. 1,1'-Bis(diphenylphosphino)ferrocenedichloropalladium(II) (0.18 g, 0.25 mmol) was added to the above solution. The reaction mixture was purged with argon for 5 min and then heated at 95 C. for 16 h. The reaction solution was cooled to room temperature, diluted with ethyl acetate, washed with water (2*) and brine, dried over sodium sulfate and concentrated under reduced pressure. The resulting residue was purified by flash column chromatography (silica gel hexanes/ethyl acetate 95:5 to 60:40) to afford the title compound (0.51 g, 96%) as a yellow solid: 1H NMR (500 MHz, CDCl3) delta 8.47 (d, J=5.0 Hz, 1H), 7.92 (d, J=16.0 Hz, 1H), 7.61-7.58 (m, 2H), 7.42-7.35 (m, 3H), 7.01 (d, J=16.0 Hz, 1H), 6.94 (d, J=5.0 Hz, 1H), 4.07 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With sodium hydrogencarbonate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In ethanol; water; toluene; for 3h;Reflux; | Preparation 2: (E)-methyl 4-styryl-1-naphthoate To a solution of <strong>[35615-97-5]methyl 4-bromo-1-naphthoate</strong>, (Preparation 1, 5.4 g, 20.4 mmol) in ethanol (50 mL) and toluene (50 mL) was added Pd(dppf)2Cl2 (760 mg, 1.0 mmol), trans-2-phenylvinylboronic acid (3.3 g, 22.4 mmol) and sodium bicarbonate aqueous solution (40 mL of 2M solution). The mixture was heated to reflux for 3 hours. The mixture was cooled to room temperature and diluted with EtOAc (150 mL) and water (75 mL). The organic phase was separated, washed with brine (50 mL), dried over sodium sulfate, and concentrated. The residue was purified by chromatography on silica gel eluting from 10:90 EtOAc:heptane to 50:50 EtOAc:heptane to afford an oil which solidified upon standing (5.3 g, 90%).1H NMR (CDCl3) delta ppm: 9.02 (1H), 8.30 (1H), 8.22 (1H), 7.91 (1H), 7.77 (1H), 7.67-7.60 (4H), 7.45 (2H), 7.36 (1H), 7.24 (1H), 4.04 (3H). |
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