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CAS No. : | 6783-05-7 | MDL No. : | MFCD00963621 |
Formula : | C8H9BO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | VKIJXFIYBAYHOE-VOTSOKGWSA-N |
M.W : | 147.97 | Pubchem ID : | 5702628 |
Synonyms : |
|
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 45.67 |
TPSA : | 40.46 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.16 cm/s |
Log Po/w (iLOGP) : | 0.0 |
Log Po/w (XLOGP3) : | 1.47 |
Log Po/w (WLOGP) : | 0.6 |
Log Po/w (MLOGP) : | 0.85 |
Log Po/w (SILICOS-IT) : | -0.29 |
Consensus Log Po/w : | 0.53 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.96 |
Solubility : | 1.64 mg/ml ; 0.0111 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.93 |
Solubility : | 1.75 mg/ml ; 0.0119 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -1.36 |
Solubility : | 6.5 mg/ml ; 0.044 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.81 |
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 |
---|---|---|
51% | Stage #1: With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; diisopropopylaminoborane; triethylamine; triphenylphosphine In tetrahydrofuran at 65℃; for 12 h; Inert atmosphere Stage #2: With methanol In tetrahydrofuran at 0℃; Inert atmosphere |
General procedure: Triphenylphosphene (0.131 g, 0.5 mmol, 20 mol percent), p-iodoanisol (0.585 g, 2.5 mmol), and triethylamine (1.78 mL, 12.5 mmol) were added to a 50 mL round-bottomed flask equipped with a sidearm, condenser, and stir bar. This solution was then degassed by alternating vacuum and argon three times. Palladium dichloride (0.023 g, 0.13 mmol, 5 mol percent) was then added under positive argon pressure. After stirring at room temperature for 15 min, diisopropylaminoborane (5 mL, 1 M solution in THF, 5 mmol) was added and the reaction mixture was degassed again by alternating vacuum and argon three times. The reaction solution was then heated to reflux. After 12 h of reflux the reaction was cooled to 0 °C and 6 mL of methanol was added through the condenser slowly (Caution: exothermic reaction with evolution of hydrogen). After 15 min of stirring all the solvent was removed under reduced pressure to yield a black solid. This solid was dissolved with sodium hydroxide (3 M, 8 mL) and subsequently washed with hexanes (3.x.10 mL). The aqueous layer was then cooled to 0 °C (ice bath) and acidified to pH <=1 with concentrated HCl, with the boronic acid usually precipitating out as a white solid. The aqueous fraction was then extracted with diethyl ether (3.x.10 mL). The organic fractions were combined, dried with magnesium sulfate and filtered. The solvent was then removed under reduced pressure yielding a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
333 mg | at 80℃; for 1 h; Inert atmosphere | To catecholborane (1.20 g, 10 mmol) in a flame-dried flask (under vacuum) under a nitrogen atmosphere, was added dropwise phenylethynyl (9 mmol) at 0 °C. After stirred at 70 °C for 4–5 h, the reaction mixture was added dropwise with water (20 mL) at 0 °C, and was stirred at 80 °C for 1 h. The resultant precipitate was filtered, washed with water and recrystallized from hot water to afford white crystals 333 mg, yield, 25percent. Mp: 164–167 °C. Lit. 162–164 °C [6a]. 1H NMR (300 MHz, CDCl3): δ 7.79 (d, J = 18.1 Hz, 1H), 7.67–7.58 (m, 2H), 7.46–7.31 (m, 3H), 6.36 (d, J = 18.1 Hz, 1H), 4.30 (s, 2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With 1H-imidazole; iron(III) chloride; In water; acetonitrile; at 20℃; for 0.5h;Inert atmosphere; | General procedure: To a solution of aryl boronic acid (1 mmol) in MeCN (4 mL) was added, sequentially, asolution of FeCl3 (8 mg, 0.05 mmol, 5 mol%) in H2O (1 mL), imidazole (204 mg, 3 mmol)and pinacol (118 mg, 1 mmol). The resulting cloudy orange mixture was stirred at roomtemperature for 30 min. The reaction was then diluted with H2O (5 mL) and extracted withEt2O (3 x 8 mL). The combined organic extracts were dried (Na2SO4) and concentrated invacuo. The resulting oil was then purified by a filtration through a silica gel plug (eluting withEt2O), affording the title compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
57.5% | With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water;Heating / reflux; | 6-Bromo-4H-pyiotado[3,2-iotab][1 ,4]oxazin-3-one (10.0 g, 44 mmole) and trans-2- phenylvinylboronic acid (9.0 g, 61 mmole) were dissolved in 1 ,4-dioxane (200 ml.) and the solution was degassed with argon. (PhbetaP^Pd (2.5 g, 2.2 mmole) was added, followed by a solution of potassium carbonate (15 g, 109 mmole) in H2O (100 ml_). The reaction was heated at reflux under argon overnight, then was cooled to room temperature and diluted with CHCI3 (400 ml_). The solution was washed sequentially with H2O and brine, dried (Na2SO4), and concentrated in vacuo. The solid residue was recrystallized from hot EtOAc to afford the title compound (6.4 g, 57.5%): MS (ES) m/e 253.0 (M + H)+. |
43% | With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water; for 17h;Heating / reflux; | D. 6-Styryl-4H-pyrido[3,2-b][1,4]oxazin-3-one. To a solution of <strong>[337463-88-4]6-bromo-4H-pyrido[3,2-b][1,4]oxazin-3-one</strong> (3.2 g, 14 mmol) in 1,4-dioxane (80 mL) was added trans-2-phenylvinylboronic acid (2.1 g, 14 mmol). After the reaction mixture was degassed with nitrogen, tetrakis(triphenylphosphine)palladium(0) (0.129 g, 0.112 mmol) and a solution of K2CO3 (3.7 g, 27 mmol) in H2O (10.7 mL) were added. The reaction was heated at reflux for 17 h, then cooled to RT, and diluted with EtOAc (300 mL). The organic layer was separated, washed with H2O (300 mL), brine (300 mL), dried (Na2SO4), and concentrated. The solid residue was purified on SiO2 (5-10% EtOAc/CHCl3) to provide 1.5 g (43%) of the title compound as a solid. MS (ESI): exact mass calculated for C15H12N2O2, 252.09; m/z found, 253.2 [M+H]+. 1H NMR (400 MHz, CDCl3): 7.53-7.00 (m, 9H), 4.66 (d, J=6.9, 2H). |
38% | With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water;Heating / reflux; | 6-Bromo-4H-pyrido[3,2-b][1 ,4]oxazin-3-one (6.0 g, 26.3 mmole) and trans-2- phenylvinylboronic acid (3.9 g, 26.3 mmole) were dissolved in 1 ,4-dioxane (150 ml_) and the solution was degassed with argon. (Ph3P)4Pd (230 mg, 0.2 mmole) was added, followed by a solution of potassium carbonate (6.9 g, 50 mmole) in H2O (20 ml_). The reaction was heated at reflux under argon overnight, then was cooled to room temperature and diluted with EtOAc (200 ml_). The solution was washed sequentially with H2O and brine, dried (Na2SO4), and concentrated in vacuo. The solid residue was purified by flash chromatography on silica gel (5-10% EtOAc/CHCl3) to afford a solid (2.5 g, 38%): MS |
38% | With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water;Heating / reflux; | d) 6-((£)-Styryl)-4H-pyrido[3,2-b][1 ,4]oxazin-3-one; 6-Bromo-4H-pyrido[3,2-b][1 ,4]oxazin-3-one (6.0 g, 26.3 mmole) and frans-2- phenylvinylboronic acid (3.9 g, 26.3 mmole) were dissolved in 1 ,4-dioxane (150 mL) and the solution was degassed with argon. (Ph3P)4Pd (230 mg, 0.2 mmole) was added, followed by a solution of potassium carbonate (6.9 g, 50 mmole) in H2O (20 mL). The reaction was heated at reflux under argon overnight, then was cooled to room temperature and diluted with EtOAc (200 mL). The solution was washed sequentially with H2O and brine, dried (Na2SO4), and concentrated in vacuo. The solid residue was purified by flash chromatography on silica gel (5-10% EtOAc/CHCl3) to afford a solid (2.5 g, 38%).MS (ES) m/z 253.0 (M + H)+. |
38% | With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water;Heating / reflux; | (d) 6-((£)-Styryl)-4H-pyrido[3,2-£>][1 ,4]oxazin-3-one; 6-Bromo-4H-pyrido[3,2-b][1 ,4]oxazin-3-one (6.0 g, 26.3 mmole) and trans-2- phenylvinylboronic acid (3.9 g, 26.3 mmole) were dissolved in 1 ,4-dioxane (150 mL) and the solution was degassed with argon. (Ph3P)4Pd (230 mg, 0.2 mmole) was added, followed by a solution of potassium carbonate (6.9 g, 50 mmole) in H2O (20 mL). The reaction was heated at reflux under argon overnight, then was cooled to room temperature and diluted with EtOAc (200 mL). The solution was washed sequentially with H2O and brine, dried (Na2SC>4), and concentrated in vacuo. The solid residue was purified by flash chromatography on silica gel (5-10% EtOAc/CHCl3) to afford a solid (2.5 g, 38%): MS (ES) m/z253.0 (M + H)+. |
38% | With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water;Heating / reflux; | 6-Bromo-4H-pyrido[3,2-b][1 ,4]oxazin-3-one (6.0 g, 26.3 mmole) and trans-2- phenylvinylboronic acid (3.9 g, 26.3 mmole) were dissolved in 1 ,4-dioxane (150 ml_) and the solution was degassed with argon. (PhbetaP^Pd (230 mg, 0.2 mmole) was added, followed by a solution of potassium carbonate (6.9 g, 50 mmole) in H2O (20 mL). The reaction was heated at reflux under argon overnight, then was cooled to room temperature and diluted with EtOAc (200 mL). The solution was washed sequentially with H2O and brine, dried (Na2SO4), and concentrated in vacuo. The solid residue was purified by flash chromatography on silica gel (5-10% EtOAc/CHCl3) to afford a solid (2.5 g, 38%).MS (ES) m/z 253.0 (M + H)+. |
38% | 6-Bromo-4/-/-pyrido[3,2-b][1 ,4]oxazin-3-one (6.0 g, 26.3 mmole) and trans-2- phenylvinylboronic acid (3.9 g, 26.3 mmole) were dissolved in 1 ,4-dioxane (150 mL) and the solution was degassed with argon. (PhbetaP^Pd (230 mg, 0.2 mmole) was added, followed by a solution of potassium carbonate (6.9 g, 50 mmole) in H2O (20 mL). The reaction was heated at reflux under argon overnight, then was cooled to room temperature and diluted with EtOAc (200 mL). The solution was washed sequentially with H2O and brine, dried (Na2SO4), and concentrated in vacuo. The solid residue was purified by flash chromatography on silica gel (5-10% EtOAc/CHCl3) to afford a solid (2.5 g, 38%): LCMS(ES) m/z253.0 (M + H)+. | |
38% | With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water;Heating / reflux; | d) 6-((E)-Styryl)-4H-pyrido[3,2-b][1,4]oxazin-3-one; 6-Bromo-4H-pyrido[3,2-b][1,4]oxazin-3-one (6.0 g, 26.3 mmole) and trans-2-phenylvinylboronic acid (3.9 g, 26.3 mmole) were dissolved in 1,4-dioxane (150 mL) and the solution was degassed with argon. (Ph3P)4Pd (230 mg, 0.2 mmole) was added, followed by a solution of potassium carbonate (6.9 g, 50 mmole) in H2O (20 mL). The reaction was heated at reflux under argon overnight, then was cooled to room temperature and diluted with EtOAc (200 mL). The solution was washed sequentially with H2O and brine, dried (Na2SO4), and concentrated in vacuo. The solid residue was purified by flash chromatography on silica gel (5-10% EtOAc/CHCl3) to afford a solid (2.5 g, 38%). MS (ES) m/z253.0 (M+H)+.; d) 6-((E)-Styryl)-4H-pyrido[3,2-b][1,4]oxazin-3-one; The bromopyridine (10c) (6.0 g, 26.3 mmole) and trans-2-phenylvinylboronic acid (3.9 g, 26.3 mmole) were dissolved in 1,4-dioxane (150 mL) and the solution was degassed with argon. (Ph3P)4Pd (230 mg, 0.2 mmole) was added, followed by a solution of potassium carbonate (6.9 g, 50 mmole) in H2O (20 mL). The reaction was heated at reflux under argon overnight, then was cooled to room temperature and diluted with EtOAc (200 mL). The solution was washed sequentially with H2O and brine, dried (Na2SO4), and concentrated in vacuo. The solid residue was purified by flash chromatography on silica gel (5-10% EtOAc/CHCl3) to afford a solid (2.5 g, 38%). MS (ES) m/z253.0 (M+H)30 . |
38% | With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water;Heating / reflux; | The bromopyridine (h) (6.0 g, 26.3 mmol) and trans-2-phenylvinylboronic acid (3.9 g, 26.3 mmol) were dissolved in 1,4-dioxane (150 ml) and the solution was degassed with argon. (Ph3P) 4Pd (230 mg, 0.2 mmol) was added, followed by a solution of potassium carbonate (6.9 g, 50 mmol) in water (20 ml). The reaction was heated at reflux under argon overnight, then was cooled to room temperature and diluted with EtOAc (200 ml). The solution was washed sequentially with water and brine, dried (Na2S04), and concentrated in vacuo. The solid residue was purified by flash chromatography on silica gel (5-10% EtOAc/CHC13) to afford a solid (2. 5g, 38%). MS (+ve ion electrospray) m/z 253 (MH+). |
38% | With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water;Heating / reflux; | The bromopyridine (h) (6.0 g, 26.3 mmole) and trans-2-phenylvinylboronic acid (3.9 g, 26.3 mmole) were dissolved in 1,4-dioxane (150 mL) and the solution was degassed with argon. (Ph3P) 4Pd (230 mg, 0.2 mmole) was added, followed by a solution of potassium carbonate (6.9 g, 50 mmole) in [H2O] (20 mL). The reaction was heated at reflux under argon overnight, then was cooled to room temperature and diluted with EtOAc (200 mL). The solution was washed sequentially with [H20] and brine, dried [(NA2SO4),] and concentrated in vacuo. The solid residue was purified by flash chromatography on silica gel (5-10% [ETOAC/CHC13)] to afford a solid (2.5 g, [38%).] MS (ES) [M/Z] 253.0 (M + H) +. |
38% | With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water;Heating / reflux; | Pyridooxazinone (3c) (6.0 g, 26.3 mmol) and trans-2-phenylvinylboronic acid (3.9 g, 26.3 mmol) were dissolved in 1,4-dioxane (150 mL) and the solution was degassed with argon. (Ph3P)4Pd (230 mg, 0.2 mmol) was added, followed by a solution of potassium carbonate (6.9 g, 50 mmol) in H2O (20 mL). The reaction was heated at reflux under argon overnight, then was cooled to room temperature and diluted with EtOAc (200 mL). The solution was washed sequentially with H2O and brine, dried (Na2SO4), and concentrated in vacuo. The solid residue was purified by flash chromatography on silica gel (5-10% EtOAc/CHCl3) to afford a solid (2.5 g, 38%). MS (ES) m/z 253.0 (M + H)+. |
38% | With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water;Heating / reflux; | The bromopyridine (305c) (6.0 g, 26.3 mmole) and trans-2-phenylvinylboronic acid (3.9 g, 26.3 mmole) were dissolved in 1,4-dioxane (150 ml) and the solution was degassed with argon. (Ph3P) 4Pd (230 mg, 0.2 mmole) was added, followed by a solution of potassium carbonate (6.9 g, 50 mmole) in H20 (20 ml). The reaction was heated at reflux under argon overnight, then was cooled to room temperature and diluted with EtOAc (200 ml). The solution was washed sequentially with H20 and brine, dried (Na2S04), and concentrated in vacuo. The solid residue was purified by flash chromatography on silica gel (5-10% EtOAc/CHC13) to afford a solid (2.5 g, 38%). MS (ES) m/z 253.0 (M + H) +. |
38% | With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water;Heating / reflux; | d) 6-((E)-Styryl)-4H-pyrido[3,2-b][1 ,4]oxazin-3-one; 6-Bromo-4H-pyrido[3,2-b][1 ,4]oxazin-3-one (6.0 g, 26.3 mmole) and trans-2- phenylvinylboronic acid (3.9 g, 26.3 mmole) were dissolved in 1 ,4-dioxane (150 mL) and the solution was degassed with argon. (Phi3P)4Pd (230 mg, 0.2 mmole) was added, followed by a solution of potassium carbonate (6.9 g, 50 mmole) in H2O (20 mL). The reaction was heated at reflux under argon overnight, then was cooled to room temperature and diluted with EtOAc (200 mL). The solution was washed sequentially with H2O and brine, dried (Na2SO4), and concentrated in vacuo. The solid residue was purified by flash chromatography on silica gel (5-10% EtOAc/CHCl3) to afford a solid (2.5 g, 38%). MS (ES) m/z 253.0 (M + H)+. |
38% | With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water;Heating / reflux; | d) 6-((£)-Styryl)-4H-pyrido[3,2-/3][1,4]oxazin-3-one; 6-Bromo-4H-pyrido[3,2-b][1,4]oxazin-3-one (6.0 g, 26.3 mmole) and trans-2-phenylvinylboronic acid (3.9 g, 26.3 mmole) were dissolved in 1,4-dioxane (150 mL) andthe solution was degassed with argon. (PhsP^Pd (230 mg, 0.2 mmole) was added,followed by a solution of potassium carbonate (6.9 g, 50 mmole) in h^O (20 mL). Thereaction was heated at reflux under argon overnight, then was cooled to room temperatureand diluted with EtOAc (200 mL). The solution was washed sequentially with h^O andbrine, dried (Na2SO4), and concentrated in vacuo. The solid residue was purified by flashchromatography on silica gel (5-10% EtOAc/CHCIs) to afford a solid (2.5 g, 38%).MS (ES) m/z 253.0 (M + H)+.; d) 6-((E)-Styryl)-4H-pyrido[3,2-£>][1,4]oxazin-3-one; The bromopyridine (1 Oc) (6.0 g, 26.3 mmole) and frans-2-phenylvinylboronic acid(3.9 g, 26.3 mmole) were dissolved in 1,4-dioxane (150 mL) and the solution wasdegassed with argon. (PhsP^Pd (230 mg, 0.2 mmole) was added, followed by a solutionof potassium carbonate (6.9 g, 50 mmole) in h^O (20 ml). The reaction was heated atreflux under argon overnight, then was cooled to room temperature and diluted withEtOAc (200 mL). The solution was washed sequentially with h^O and brine, dried(Na2SC>4), and concentrated in vacuo. The solid residue was purified by flashchromatography on silica gel (5-10% EtOAc/CHCIs) to afford a solid (2.5 g, 38%).MS (ES) m/z 253.0 (M + H)+. |
38% | With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water;Heating / reflux; | (d) 6-((E)-Styryl)-4/-/-pyrido[3,2-b][1,4]oxazin-3-one; 6-Bromo-4/-/-pyrido[3,2-b][1,4]oxazin-3-one (6.0 g, 26.3 mmole) and trans-2-phenylvinylboronic acid (3.9 g, 26.3 mmole) were dissolved in 1,4-dioxane (150 mL) and the solution was degassed with argon. (Phi3P)4Pd (230 mg, 0.2 mmole) was added, followed by a solution of potassium carbonate (6.9 g, 50 mmole) in H2O (20 mL). The reaction was heated at reflux under argon overnight, then was cooled to room temperature and diluted with EtOAc (200 mL). The solution was washed sequentially with H2O and brine, dried (Na2S04), and concentrated in vacuo. The solid residue was purified by flash chromatography on silica gel (5-10% EtOAc/CHCl3) to afford a solid (2.5 g, 38%): LCMS (ES) m/z 253.0 (M + H)+. |
38% | With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water;Heating / reflux; | d) 6-((E)-Styryl)-4H-pyrido[3,2-b][1 ,4]oxazin-3-one 6-Bromo-4H-pyrido[3,2-b][1 ,4]oxazin-3-one (6.0 g, 26.3 mmole) and trans-2- phenylvinylboronic acid (3.9 g, 26.3 mmole) were dissolved in 1 ,4-dioxane (150 ml.) and the solution was degassed with argon. (PhbetaP^Pd (230 mg, 0.2 mmole) was added, followed by a solution of potassium carbonate (6.9 g, 50 mmole) in H2O (20 ml_). The reaction was heated at reflux under argon overnight, then was cooled to room temperature and diluted with EtOAc (200 ml_). The solution was washed sequentially with H2O and brine, dried (Na2SO4), and concentrated in vacuo. The solid residue was purified by flash chromatography on silica gel (5-10% EtOAc/CHCl3) to afford a solid (2.5 g, 38%); MS (ES) m/z253.0 (M + H)+. |
38% | With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water;Heating / reflux;Product distribution / selectivity; | 6-Bromo-4H-pyrido[3,2-b][1 ,4]oxazin-3-one (6.0 g, 26.3 mmole) and trans-2- phenylvinylboronic acid (3.9 g, 26.3 mmole) were dissolved in 1 ,4-dioxane (150 mL) and the solution was degassed with argon. (Ph3P)4Pd (230 mg, 0.2 mmole) was added, followed by a solution of potassium carbonate (6.9 g, 50 mmole) in H2O (20 mL). The reaction was heated at reflux under argon overnight, then was cooled to room temperature and diluted with EtOAc (200 mL). The solution was washed sequentially with H2O and brine, dried (Na2SO4), and concentrated in vacuo. The solid residue was purified by flash chromatography on silica gel (5-10% EtOAc/CHCl3) to afford a solid (2.5 g, 38%): LCMS (ES) m/z253.0 (M + H)+. d. 6-((E)-styryl)-4H-pyrido[3,2-b][1,4]oxazin-3-one The bromopyridine (1 Oc) (6.0 g, 26.3 mmole) and frans-2-phenylvinylboronic acid (3.9 g, 26.3 mmole) were dissolved in 1 ,4-dioxane (150 mL) and the solution was degassed with argon. (Ph3P)4Pd (230 mg, 0.2 mmole) was added, followed by a solution of potassium carbonate (6.9 g, 50 mmole) in H2O (20 mL). The reaction was heated at reflux under argon overnight, then was cooled to room temperature and diluted with EtOAc (200 mL). The solution was washed sequentially with H2O and brine, dried (Na2SO4), and concentrated in vacuo. The solid residue was purified by flash chromatography on silica gel (5-10% EtOAc/CHCl3) to afford a solid (2.5 g, 38%): LCMS (ES) m/z 253.0 (M + H)+. |
38% | With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water;Heating / reflux; | 6-Bromo-4H-pyrido[3,2-b][1 ,4]oxazin-3-one (6.0 g, 26.3 mmole) and trans-2- phenylvinylboronic acid (3.9 g, 26.3 mmole) were dissolved in 1 ,4-dioxane (150 mL) and the solution was degassed with argon. (Ph3P)4Pd (230 mg, 0.2 mmole) was added, followed by a solution of potassium carbonate (6.9 g, 50 mmole) in H2O (20 mL). The reaction was heated at reflux under argon overnight, then was cooled to room temperature and diluted with EtOAc (200 mL). The solution was washed sequentially with water and brine, dried (Na2SO4), and concentrated in vacuo. The solid residue was purified by flash chromatography (silica, 5-10% ethyl acetate in chloroform) to afford the title compound as an off-white solid (2.5 g, 38%): LCMS (ES) m/z 253.0 (M + H)+ |
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 |
---|---|---|
A suspension of 2-chloro-6-methyl-isonicotinic acid (171.6 mg, 1 MMOL), (E) -2- PHENYL-ETHENEBORONIC acid (180.0 mg, 1.2 MMOL), K2CO3 (414 mg), Pd (dppf) C12- CH2CI2 (27 mg) in CH3CN-H20 (3: 1,10 mL) is stirred under argon at 90C for 15 h. The solution is cooled to r. t. and aq. hydrochloric acid (2 M, 1.5 mL) is added to adjust the pH at 3. The mixture is evaporated to dryness and purified by reversed phase MPLC to provide the title compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | In dichloromethane; | Example 4 Preparation of D-homophenylalanine. To a stirred solution of glyoxylic acid monohydrate (291 mg, 3.163 mmol) in dichloromethane (14 mL) was added (S)-(-)-2-phenylglycinol (434 mg, 3.163 mmol) in one portion. After 5 min (E)-2-phenylethenyl boronic acid (469 mg, 3.169 mmol) was added. and the reaction mixture was stirred vigorously at room temperature for 12 hours. The precipitate was isolated by filtration, washed with cold dichloromethane (15 mL) and acetone (10 mL) and dried under vacuum to give the expected adduct (733 mg, 78% yield, >99% de). 1H-NMR (360 MHz, d6-DMSO) delta 7.2-7.5 (m, 10H), 6.54 (d, J=15.2 Hz, 1H), 6.20 (dd, J=15.2 Hz, 7.3 Hz, 1H), 3.84 (m, 1H), 3.64 (d, J=7.3 Hz, 1H), 3.45 (d, J=7.1 Hz, 2H). 13-NMR (90 MHz, d6-DMSO) delta 172.83, 139.79, 136.23, 131.07, 128.62, 128.34, 127.68, 127.51, 126.95, 126.38, 126.25, 65.97, 63.02, 60.96. HRMS-CI(M++1) calcd 298.1365, obsd 298.1449. Anal. Calcd for C18H19NO3: C, 72.71; H, 6.44; N, 4.71. Found: C, 72.27; H, 6.41 N, 4.69. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With potassium carbonate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In dimethyl sulfoxide; at 90℃; for 1h; | c) (£)-2-Methoxy-4-styrylpyridine; Chemical Formula: C 14H13NOExact Mass: 21 1.10 Molecular Weight: 21 1.26 [00182] <strong>[100367-39-3]4-Bromo-2-methoxypyridine</strong> (1 85 g, 9.84 mmol), (£)-phenylvinylboronic acid (4.3 g, 30 mmol), K2CO3 (4.0 g, 30 mmol) and [1, 1 '-Bis- (diphosphenylphosphino)ferrocene]dichloropalladium(II) (PdCl2dppf) (400 mg, 0.5 mmol) were stirred in DMSO (15 mL) under vacuum for 30 min. The flask was flushed <n="108"/>with nitrogen and the mixture was heated at 90 0C for 30 min. Upon cooling, the mixture was diluted with methylene chloride and washed with 5% lithium chloride solution (5chi), dried, concentrated, and the residue was purified by column chromatography (silica gel, hexanes/ethyl acetate, 97 3 to 75:25) to provide the title compound (1 93 g, 93%) as an orange oil: 1H NMR (300 MHz, CDCl3) delta 8.12 (d, J= 5.2 Hz, IH), 7.51 (m, 2H), 7.40-7.22 (m, 4H), 7.02-6.94 (m, 2H), 6.78 (s, IH), 3.95 (s, 3H). |
93% | With potassium carbonate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In dimethyl sulfoxide; at 90℃; for 0.5h; | <strong>[100367-39-3]4-Bromo-2-methoxypyridine</strong> (1.85 g, 9.84 mmol), (E)-phenylvinylboronic acid (4.3 g, 30 mmol), K2CO3 (4.0 g, 30 mmol) and PdCl2(dppf) (400 mg, 0.5 mmol) were stirred in DMSO (15 mL) under vacuum for 30 min. The flask was flushed with nitrogen and the mixture was heated to 90 0C for 30 min. Upon cooling, the mixture was diluted with methylene chloride and washed with 5% lithium chloride solution (5chi), dried, concentrated, and the residue was purified by flash column chromatography (silica gel, hexanes/ethyl acetate, 97:3 to 75:25) to provide the title compound (1.93 g, 93%) as an orange oil: 1H NMR (300 MHz, CDCl3) delta 8.12 (d, J= 5.2 Hz, IH), 7.51 (m, 2H), 7.40- 7.22 (m, 4H), 7.02-6.94 (m, 2H), 6.78 (s, IH), 3.95 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
17% | With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; N,N-dimethyl-formamide; for 10h;Heating / reflux; | In a reaction container, 1.17 g (0.005 mol) of the compound (L-1), 0.76 g (0.00625 mol) of trans-2-phenylvinylboric acid, 1.06g (0.01 mol) of sodium carbonate and 0.35 g (0.0003 mol) of tetrakis (triphenylphosphine)palladium (0) were weighed and placed, and a dimethylformamide/ethanol solution mixture (35 mL/5 mL) was added. The reaction mixture was refluxed for 10 hours under nitrogen airflow. The reaction mixture was poured in water (100 mL) and extraction was performed with an ethyl acetate/hexane (1/1) solution (100 mL). Thereafter, the organic layer was washed with water (100 mL), a 5% aqueous sodium hydrogen carbonate solution (100 mL) and a saturated salt solution (100 mL). After the organic layer was dried over sodium sulfate, purification was performed by silica gel column chromatography (toluene/chloroform). The solvent was distilled off to obtain 0.28 g (0.00083 mol) of the compound (L-4) in a yield of 17%. LC-MS (positive) m/z:258 ([M+H]+) 1 H NMR (300MHz, CDC 13) delta 7. 1 5 (s, 1H) , delta 7.19 (s, 1H) , delta 7.31 (d, J = 7.5 Hz, 1 H) , delta 7.39 (m, 3H), delta 7.49 (m, 2H) , delta 7.56 (d, J=7. 5Hz, 2H) , delta 7.75 (d, J = 8. 4 Hz, 1H) , delta 7.93 (dd, J=2.3, 8.3 Hz, 1H) , delta 8.03 (d, J=8. 4 H z, 2H) , delta 8.79 (s, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
57% | With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; N,N-dimethyl-formamide; for 10h;Heating / reflux; | In a reaction container, 1.17g (0.005 mol) of the compound (L-2), 0.76 (0.00625 mol) of trans-2-phenylvinylboric acid, 1.06 g (0.01 mol) of sodium carbonate and 0.35 g (0.0003 mol) of tetrakis (triphenylphosphine)palladium (0) were weighed and placed and a dimethylformamide/ethanol solution mixture (35 mL/5 mL) was added. The reaction mixture was refluxed for 10 hours under nitrogen airflow. The reaction mixture was poured in water (100 mL) and extraction was performed with an ethyl acetate/hexane (1/1) solution (100 mL). The organic layer was washed with water (100 mL), a 5% aqueous sodium hydrogen carbonate solution (100 mL) and a saturated salt solution (100 mL). After the organic layer was dried over sodium sulfate, purification was performed by silica gel column chromatography (toluene/chloroform). The solvent was distilled off to obtain 0.73 g (0.00284 mol) of the compound (L-6) in a yield of 57%. LC-MS (positive) m/z:258 ([M+H]+) 1 H NMR (3 0 0MHz, CDC 13) delta 7. 1 7 7 (s, 1H) , delta 7. 1 8 2 (s, 1H) , delta 7. 2 7 (m, 2 H) , delta 7. 3 8 (d d, J=7. 2, 7. 9 H z, 2 H) , delta 7. 5 5 (d, J=7. 7 Hz, 2H) , delta 7. 6 3 (d, J=8. 3 H z, 2H) , delta 7. 7 6 (m, 2H) , delta 8. 0 2 (d, J=8. 3Hz, 2H) , delta 8. 70 (d, J=4. 8Hz, 1H). |
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 |
---|---|---|
With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In water; at 90℃; for 5h; | Production Example 10; To a mixture of <strong>[58481-11-1]methyl 2-chloroisonicotinate</strong>, Pd(PPh3)4, and [(E)-2-phenylvinyl]boric acid in dioxane was added a 2 M aqueous Na2CO3 solution, followed by stirring at 90°C for 5 hours. To the reaction mixture was added water, and the aqueous layer was extracted with EtOAc. The organic layer was dried over MgSO4, and the filtrate was then concentrated under reduced pressure. The residue was purified by medium-pressure preparative liquid chromatography (silica gel, YAMAZEN YFLC WPrep2XY, hexane:EtOAc) to obtain methyl 2-[(E)-2-phenylvinyl]isonicotinate as a pale yellow solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With caesium carbonate; triphenylphosphine;palladium diacetate; In N,N-dimethyl-formamide; at 70℃; for 5.0h; | (E)-Dimethyl 3-styrylpyridine-2,4-dicarboxylate Z4'A stirred suspension of 3-bromopyridine 11 (500 mg, 1.82 mmol, 1 eq.), (E)-styryl boronic acid (300 mg, 2.01 mmol, 1.1 eq.), Cs2CO3 (650 mg, 2.01 mmol, 1.1 eq.), Pd(OAc)2 (40 mg,0.182 mmol, 0.1 eq.) and PPh3 (100 mg, 0.365 mmol, 0.2 eq.) in anhydrous DMF (10 mL) was heated to 70 0C for 5 h in an oil bath. The reaction mixture was diluted with EtOAc (50 mL) and washed with water (50 mL). The organic layer was dried (Na2SO4) and concentrated in vacuo.The residue was purified by automated flash column chromatography (Biotage KP-SIL SNAP 25 g cartridge, eluting with EpsilontOAc/hexane) to afford Z4' (322 mg, 60%) as an off-white solid.1U NMR deltaH (400 MHz; CDCl3) 3.86 (s, 3H, OCH3), 3.89 (s, 3Eta, OCH3), 6.59 (d, J=16.5 Hz, IH, CH=CH), 7.23-7.30 (t, J=8.0 Hz, IH, ArHpara), 7.34 (t, J=8.0 Hz, 2H, ArHmeta), 7.46 (d, J=7.0 Hz, 2H, ArHortho), 7.64 (d, J=16.5 Hz, IH, CH=CH), 7.71 (d, J=5.0 Hz, IH, pyHmeta), 8.65 (d, J=5.0 Hz, IH, pyHortho); 13C NMR deltac (100 MHz; CDCl3) 52.8 (CH3), 52.8 (CH3), 123.5 (CH=CH), 124.6 (ArCH), 126.7 (ArCH), 128.4 (ArCH), 128.7 (ArCH), 133.0 (ArQ, 135.1 (CH=CH), 136.5 (ArQ, 139.0 (ArQ, 147.9 (ArCH), 149.8 (ArQ, 166.5 (CO), 166.7 (CO); IR vmax (filmycrn 1 2953, 1735, 1447, 1434, 1313, 1269, 1197, 1166, 1143, 1130; HRMS (EpsilonSI+) for C17H15NNaO4 requires 320.0893, found (M+Na*) 320.0893; |
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). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
18% | With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,4-dioxane; water; at 90℃; for 18h;Inert atmosphere; | (E)-tert-butyl 4-styrylbenzoate. To a solution of (E)-styrylboronic acid (289 mg, 1.95 mmol) in mixed solution of dioxane and water (4: 1, 15 mL) were added tert-butyl 4- bromobenzoate (500 mg, 1.95 mmol), tetrakis(triphenylphosphine)palladium (225 mg, 0.2 mmol) and sodium carbonate (622 mg, 5.9 mmol). The mixture was stirred at 90°C under nitrogen atmosphere for 18 hours. Once start material has been consumed, the mixture was concentrated to give a residue and the residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate = 25: 1) to give (E)-tert-butyl 4-styrylbenzoate (0.1 g, 18percent>). The product was used for the next step directly without further purification. |
18% | With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,4-dioxane; water; at 90℃; for 18h;Inert atmosphere; | To a solution of (E)-styrylboronic acid (289 mg, 1.95 mmol) in mixed solution of dioxane and water (4:1, 15 mL) were added tert-butyl 4-bromobenzoate (500 mg, 1.95 mmol), tetrakis(triphenylphosphine)palladium (225 mg, 0.2 mmol) and sodium carbonate (622 mg, 5.9 mmol). The mixture was stirred at 90° C. under nitrogen atmosphere for 18 hours. Once start material has been consumed, the mixture was concentrated to give a residue and the residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=25:1) to give (E)-tert-butyl 4-styrylbenzoate (0.1 g, 18percent). The product was used for the next step directly without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,4-dioxane; for 24h;Inert atmosphere; Reflux; | To a reaction vessel (lO0mL) in a nitrogen environment containing 3 (5g, I 5.7mmol) were added trans-phenylvinylboronic acid 4 (2.7g, 1 8mmol), tetrakis triphenylphosphine (907mg, 0.8mmol), sodium carbonate (4.2g, 39mmol) in 1 ,4-dioxane(1 OOmL). The mixture was stirred at refiux for 24 hours until consumption of starting material followed by TLC. The product was cooled to room temperature; it was filtered on celite. The solution was dried on MgSO4, filtered and evaporated. The residue was purified by chromatography (c-hexane:ethyl acetate99: 1, then 98:2) to afford 5-bromo-2-chloro-3- ((E)-styryl)pyridine 5 (yield: 93%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; caesium carbonate; In 1,4-dioxane; water; at 80℃; for 3h;Inert atmosphere; | Step 2 1,4-Dioxane (2 mL) and water (one drop) were added to <strong>[39824-26-5]((3aR,4R,6R,6aR)-6-(6-chloro-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol</strong> (150 mg, 0.459 mmol) obtained in Step 1, (E)-styrylboronic acid (136 mg, 0.918 mmol), 1,1'-bis(diphenylphosphino)ferrocene-palladium(II) dichloride-dichloromethane complex (37.5 mg, 0.031 mmol), and cesium carbonate (449 mg, 1.38 mmol), and the mixture was stirred at 80 C. for 3 hours under a nitrogen atmosphere. After the reaction solution was cooled to room temperature, saturated brine was added thereto, and the mixture was extracted with ethyl acetate and dried over sodium sulfate. The residue obtained by evaporating the solvent under reduced pressure was purified by column chromatography (heptane/ethyl acetate) to obtain ((3aR,4R,6R,6aR)-2,2-dimethyl-6-(6-((E)-styryl)-9H-purin-9-yl)tetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol (90.1 mg, yield: 50%). ESI-MS (m/z): 395 (M+1) |
50% | With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; caesium carbonate; In 1,4-dioxane; water; at 80℃; for 3h;Inert atmosphere; | Step 2 1,4-Dioxane (2 mL) and water (one drop) were added to <strong>[39824-26-5]((3aR,4R,6R,6aR)-6-(6-chloro-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol</strong> (150 mg, 0.459 mmol) obtained in Step 1, (E)-styrylboronic acid (136 mg, 0.918 mmol), 1,1'-bis(diphenylphosphino)ferrocene-palladium(II) dichloride-dichloromethane complex (37.5 mg, 0.031 mmol), and cesium carbonate (449 mg, 1.38 mmol), and the mixture was stirred at 80 C. for 3 hours under a nitrogen atmosphere. After the reaction solution was cooled to room temperature, saturated brine was added thereto, and the mixture was extracted with ethyl acetate and dried over sodium sulfate. The residue obtained by evaporating the solvent under reduced pressure was purified by column chromatography (heptane/ethyl acetate) to obtain ((3aR,4R,6R,6aR)-2,2-dimethyl-6-(6-((E)-styryl)-9H-purin-9-yl)tetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol (90.1 mg, yield: 50%). ESI-MS (m/z): 395 (M+1) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In ethanol; water; toluene; for 20h;Reflux; Inert atmosphere; | In a reaction vessel, <strong>[55583-59-0]4,6-dichloropyrimidine-2,5-diamine</strong> (500 mg, 2.79 mmol), trans-2-phenylvinylboronic acid (0.945 g, 6.42 mmol), sodium carbonate (1.48 g, Ethanol (7 mL) and distilled water (7 mL) were added to a solution of 14.0 mmol) and tetrakis (triphenyl phosphine) palladium (0) (322 mg, 0.279 mmol) in toluene (28 mL) at room temperature, and argon was added. After stirring under heating and reflux conditions for 20 hours under an atmosphere, the reaction solution was cooled to room temperature. Distilled water (8 mL) was added and stirred, and the separated aqueous layer was extracted three times with ethyl acetate (12 mL). After that, the whole organic layer is combined, saturated aqueous sodium chloride solution (12 mL) is added thereto, the mixture is stirred and washed, anhydrous sodium sulfate is added to the separated organic layer for dehydration, and the filtrate after filtration is depressurized. Concentrated. The concentrate thus obtained is purified by flash column chromatography (silica gel, n-hexane / ethyl acetate),4,6-Di ((E) -styryl) pyrimidine-2,5-diamine(0.72 g, 82% yield). |
Tags: 6783-05-7 synthesis path| 6783-05-7 SDS| 6783-05-7 COA| 6783-05-7 purity| 6783-05-7 application| 6783-05-7 NMR| 6783-05-7 COA| 6783-05-7 structure
[ 172975-69-8 ]
3,5-Dimethylphenylboronic acid
Similarity: 0.74
[ 154230-29-2 ]
(E)-(4-Chlorostyryl)boronic acid
Similarity: 0.73
[ 172975-69-8 ]
3,5-Dimethylphenylboronic acid
Similarity: 0.74
[ 154230-29-2 ]
(E)-(4-Chlorostyryl)boronic acid
Similarity: 0.73
[ 154230-29-2 ]
(E)-(4-Chlorostyryl)boronic acid
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[ 83947-56-2 ]
E-Phenylethenylboronic acid, pinacol ester
Similarity: 0.60
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P310 | Immediately call a POISON CENTER or doctor/physician. |
P311 | Call a POISON CENTER or doctor/physician. |
P312 | Call a POISON CENTER or doctor/physician if you feel unwell. |
P313 | Get medical advice/attention. |
P314 | Get medical advice/attention if you feel unwell. |
P315 | Get immediate medical advice/attention. |
P320 | |
P302 + P352 | IF ON SKIN: wash with plenty of soap and water. |
P321 | |
P322 | |
P330 | Rinse mouth. |
P331 | Do NOT induce vomiting. |
P332 | IF SKIN irritation occurs: |
P333 | If skin irritation or rash occurs: |
P334 | Immerse in cool water/wrap n wet bandages. |
P335 | Brush off loose particles from skin. |
P336 | Thaw frosted parts with lukewarm water. Do not rub affected area. |
P337 | If eye irritation persists: |
P338 | Remove contact lenses, if present and easy to do. Continue rinsing. |
P340 | Remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P341 | If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P342 | If experiencing respiratory symptoms: |
P350 | Gently wash with plenty of soap and water. |
P351 | Rinse cautiously with water for several minutes. |
P352 | Wash with plenty of soap and water. |
P353 | Rinse skin with water/shower. |
P360 | Rinse immediately contaminated clothing and skin with plenty of water before removing clothes. |
P361 | Remove/Take off immediately all contaminated clothing. |
P362 | Take off contaminated clothing and wash before reuse. |
P363 | Wash contaminated clothing before reuse. |
P370 | In case of fire: |
P371 | In case of major fire and large quantities: |
P372 | Explosion risk in case of fire. |
P373 | DO NOT fight fire when fire reaches explosives. |
P374 | Fight fire with normal precautions from a reasonable distance. |
P376 | Stop leak if safe to do so. Oxidising gases (section 2.4) 1 |
P377 | Leaking gas fire: Do not extinguish, unless leak can be stopped safely. |
P378 | |
P380 | Evacuate area. |
P381 | Eliminate all ignition sources if safe to do so. |
P390 | Absorb spillage to prevent material damage. |
P391 | Collect spillage. Hazardous to the aquatic environment |
P301 + P310 | IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. |
P301 + P312 | IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. |
P301 + P330 + P331 | IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. |
P302 + P334 | IF ON SKIN: Immerse in cool water/wrap in wet bandages. |
P302 + P350 | IF ON SKIN: Gently wash with plenty of soap and water. |
P303 + P361 + P353 | IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower. |
P304 + P312 | IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell. |
P304 + P340 | IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing. |
P304 + P341 | IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P305 + P351 + P338 | IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. |
P306 + P360 | IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes. |
P307 + P311 | IF exposed: call a POISON CENTER or doctor/physician. |
P308 + P313 | IF exposed or concerned: Get medical advice/attention. |
P309 + P311 | IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician. |
P332 + P313 | IF SKIN irritation occurs: Get medical advice/attention. |
P333 + P313 | IF SKIN irritation or rash occurs: Get medical advice/attention. |
P335 + P334 | Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages. |
P337 + P313 | IF eye irritation persists: Get medical advice/attention. |
P342 + P311 | IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician. |
P370 + P376 | In case of fire: Stop leak if safe to Do so. |
P370 + P378 | In case of fire: |
P370 + P380 | In case of fire: Evacuate area. |
P370 + P380 + P375 | In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion. |
P371 + P380 + P375 | In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion. |
Storage | |
Code | Phrase |
P401 | |
P402 | Store in a dry place. |
P403 | Store in a well-ventilated place. |
P404 | Store in a closed container. |
P405 | Store locked up. |
P406 | Store in corrosive resistant/ container with a resistant inner liner. |
P407 | Maintain air gap between stacks/pallets. |
P410 | Protect from sunlight. |
P411 | |
P412 | Do not expose to temperatures exceeding 50 oC/ 122 oF. |
P413 | |
P420 | Store away from other materials. |
P422 | |
P402 + P404 | Store in a dry place. Store in a closed container. |
P403 + P233 | Store in a well-ventilated place. Keep container tightly closed. |
P403 + P235 | Store in a well-ventilated place. Keep cool. |
P410 + P403 | Protect from sunlight. Store in a well-ventilated place. |
P410 + P412 | Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF. |
P411 + P235 | Keep cool. |
Disposal | |
Code | Phrase |
P501 | Dispose of contents/container to ... |
P502 | Refer to manufacturer/supplier for information on recovery/recycling |
Physical hazards | |
Code | Phrase |
H200 | Unstable explosive |
H201 | Explosive; mass explosion hazard |
H202 | Explosive; severe projection hazard |
H203 | Explosive; fire, blast or projection hazard |
H204 | Fire or projection hazard |
H205 | May mass explode in fire |
H220 | Extremely flammable gas |
H221 | Flammable gas |
H222 | Extremely flammable aerosol |
H223 | Flammable aerosol |
H224 | Extremely flammable liquid and vapour |
H225 | Highly flammable liquid and vapour |
H226 | Flammable liquid and vapour |
H227 | Combustible liquid |
H228 | Flammable solid |
H229 | Pressurized container: may burst if heated |
H230 | May react explosively even in the absence of air |
H231 | May react explosively even in the absence of air at elevated pressure and/or temperature |
H240 | Heating may cause an explosion |
H241 | Heating may cause a fire or explosion |
H242 | Heating may cause a fire |
H250 | Catches fire spontaneously if exposed to air |
H251 | Self-heating; may catch fire |
H252 | Self-heating in large quantities; may catch fire |
H260 | In contact with water releases flammable gases which may ignite spontaneously |
H261 | In contact with water releases flammable gas |
H270 | May cause or intensify fire; oxidizer |
H271 | May cause fire or explosion; strong oxidizer |
H272 | May intensify fire; oxidizer |
H280 | Contains gas under pressure; may explode if heated |
H281 | Contains refrigerated gas; may cause cryogenic burns or injury |
H290 | May be corrosive to metals |
Health hazards | |
Code | Phrase |
H300 | Fatal if swallowed |
H301 | Toxic if swallowed |
H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
H304 | May be fatal if swallowed and enters airways |
H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
Sorry,this product has been discontinued.
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