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CAS No. : | 532924-25-7 | MDL No. : | MFCD10696660 |
Formula : | C6H5BClNO4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | PURYLRLRXKALOG-UHFFFAOYSA-N |
M.W : | 201.37 g/mol | Pubchem ID : | 10214460 |
Synonyms : |
|
Num. heavy atoms : | 13 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 50.1 |
TPSA : | 86.28 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.62 cm/s |
Log Po/w (iLOGP) : | 0.0 |
Log Po/w (XLOGP3) : | 1.28 |
Log Po/w (WLOGP) : | -0.07 |
Log Po/w (MLOGP) : | 0.59 |
Log Po/w (SILICOS-IT) : | -2.16 |
Consensus Log Po/w : | -0.07 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.1 |
Solubility : | 1.58 mg/ml ; 0.00786 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.69 |
Solubility : | 0.41 mg/ml ; 0.00204 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -1.29 |
Solubility : | 10.3 mg/ml ; 0.0513 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 3.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.23 |
Signal Word: | Warning | Class: | |
Precautionary Statements: | P501-P270-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330 | UN#: | |
Hazard Statements: | H302-H315-H319 | Packing Group: | |
GHS Pictogram: |
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* 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; water at 60℃; for 2h; Inert atmosphere; | 23 (Comparative Example 23); 5-Chloro-4 ' -fluorobiphenyl-2-amineTo water (2 mL) and dimethoxyethane (20 mL) , 5-chloro-2- nitrophenylboronic acid (3.27 g, 16.4 mmol), 1-fluoro-4-iodobenzene (3.65 g, 16.4 mmol), tetrakis (triphenylphosphine) palladium (0.95 g, 0.82 mmol) and potassium carbonate (6.81 g, 49.3 mmol) were added, and the mixture was stirred under a nitrogen atmosphere at 600C for 2 hours. After the reaction, the reaction mixture was cooled to room temperature and ethyl acetate (30 mL) was added. After the organic phase was washed with water (30 mL) and saturated brine (20 mL) , it was dried with sodium sulfate. The solvent was distilled off under reduced pressure to give 5-chloro-4 ' -fluoro-2- nitrobiphenyl as a crude product. The obtained compound was used for the subsequent reaction without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In ethanol; toluene at 110℃; for 0.166667h; Microwave irradiation; | i-2.B Preparation of methyl 2-(4-(5-chloro-2-nitrophenyl)-2-oxopyridin-1(2H)-yl)-3-phenylpropanoate (i-2b) A degassed suspension of 1-lb (500 mg, 1.49 mmol), (5-chloro-2-nitrophenyl)boronicacid (329 mg, 1.64 mmol), potassium carbonate (206 mg, 1.49 mmol), and [1,1’-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (163 mg, 0.22 mmol) in EtOH:toluene (10 mL of a 4:1 mixture) was heated in a microwave reactor to 110 °C for 10 min. After cooling to rt, the reaction mixture was diluted with EtOAc and filtered through a colunm of Celite, which was rinsed with additional portions of EtOAc. The combined organics were dried(Na2SO4), filtered and concentrated, and the resulting crude residue was purified by flash chromatography on silica gel (gradient elution; 0%-30% EtOAc/hexanes as eluent) to afford the title compound as a white solid. m/z (ES) 413 (MH)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium phosphate; dichloro[1,1′-bis[bis(1,1-dimethylethyl)phosphino]ferrocene-P,P′]palladium; sodium phosphate In 1-methyl-pyrrolidin-2-one at 90℃; for 16h; | i-2.A Preparation of 2-(4-(5-chloro-2-nitrophenyl)-2-oxopyridin-1(2H)-yl)-3-phenylpropanoic acid (i-2a) A degassed suspension of i-ic (100 mg, 0.3 10 mmol), (5-chloro-2-nitrophenyl)boronic acid (94 mg, 0.466 mmol), potassium phosphate, tribasic (0.78 mL of a 1M aq. solution, 0.778 mmol), and 1,1 ‘-bis(di-tert-butylphosphino)ferrocenepalladium dichloride (20 mg, 0.031 mmol)in NMP (2.6 mL) was heated to 90 °C. After 16 h, the reaction mixture was cooled to rt, and partitioned between EtOAc and water. The layers were separated, the aq. layer was acidified with 1M HC1 and extracted with EtOAc. The combined organics were washed with water and brine, dried (MgSO4), filtered and concentrated to afford the title compound i-2a as a crude brown solid. m/z (ES) 399 (MH)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In tetrahydrofuran; water at 100℃; for 1h; Microwave irradiation; Sealed tube; Inert atmosphere; | 1.3; 2.3 Step 3. fert-Butyl 4-(2-(5 -(5 -chloro-2-nitrophenyl)pyridin-2-yl)-3 -phenylpropanamido) benzoate(l-C) Step 3. fert-Butyl 4-(2-(5 -(5 -chloro-2-nitrophenyl)pyridin-2-yl)-3 -phenylpropanamido) benzoate(l-C) A mixture of tert-butyl 4-(2-(5-bromopyridin-2-yl)-3 -phenylpropanamido) benzoate (1-B) (0.475 g, 0.987 mmol), (5-chloro-2-nitrophenyl)boronic acid (0.397 g, 1.973 mmol), PdCl2(dppf)-CH2Cl2 adduct (0.16 g, 0.197 mmol) in THF(5 mL) was added potassium phosphate tribasic aqueous solution (2 mL, 4 mmol, 2M) in a microwave tube. The tube was sealed, degassed and refilled with N2. The mixture was heated at 100°C by microwave for 1 hour. The reaction mixture was diluted with water, extracted with EtOAc, and the organic layers were combined and washed with brine and dried over Na2S04. Solvent was removed in vacuo. The residue was purified by column chromatography on silica gel, eluting with EtOAc/hexane to give product 1-C. 1H NMR (500 MHz, CDC13) δ: 1.66 (9H, s), 3.32 (1 H, dd), 3.60 (1 H, dd), 4.10 (1 H, m), 7.05 (2 H, d), 7.10-7.24 (4H,m), 7.42 (1 H, d), 7.58-7.63 (4H, m), 7.95 (2 H, d), 8.03 (1 H, d), 8.59 (1 H, s), 10.00 (1 H, s). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate In tetrahydrofuran; water at 100℃; for 1h; Inert atmosphere; Microwave irradiation; | 7.4 Step 4. 2-(l -(5-(5-chloro-2-nitrophenyl)pyridin-2-yl)-2-phenylethyl)-5-fluoro- 1 -((2- (trimethylsilyl)ethoxy)methyl)-lH-benzo[dlimidazole) (3-D): A reaction mixture of 2-(l-(5- Bromopyridin-2-yl)-2-phenylethyl)-5 -fluoro- 1 -((2-(trimethylsilyl)ethoxy)methyl) - 1 H- benzo[d]imidazole (3-C) (150 mg, 0.28 mmol), PdCl2(dppf) (62.5 mg, 0.085 mmol), (5-chloro- 2-nitrophenyl)boronic acid (86 mg, 0.427 mmol) and potassium phosphate tribasic aq. solution (0.57 ml, 1.14 mmol, 2M) in THF (2 ml) was degassed and refilled with N2. It was heated at 100°C for 1 hour by microwave. The reaction mixture was diluted with water, extracted with EtOAc, the organic was washed with brine, dried over Na2S04. Solvent was removed in vacuo. The residue was purified by column chromatography on silica gel, eluting with EtOAc/hexane to give the product (3-D). 1H NMR (500 MHz, CDC13) δ: -0.097 (9H, s), 0.79-0.64 (2H, m), 3.30- 3.18 (2H, m), 3.62 (1H, m), 3.89 (1H, m), 4.90 (1H, m), 5.27 (1H, dd), 5.45 (1H, dd), 7.03 (1H, m), 7.23-7.12 (6H, m), 7.31 (1H, m), 7.36 (1H, m), 7.60-7.49 (3H, m), 7.79 (1H, m), 7.96 (1H, d,) 8.46 (1H, s). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: potassium phosphate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / tetrahydrofuran; water / 1 h / 100 °C / Inert atmosphere; Microwave irradiation 2: tin(II) chloride dihdyrate; ethanol / ethyl acetate / 3 h / 50 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With bis-triphenylphosphine-palladium(II) chloride; sodium hydrogencarbonate; 2-(dicyclohexylphosphino)-1-(2-methoxyphenyl)-1H-pyrrole In 1,4-dioxane; water at -100 - 100℃; for 5h; Autoclave; | 25 General procedure: (3a, 5a) General procedure: The reaction was carried out in an autoclave containing a 10 mL Teflon reaction tube. Pd(PPh3)2Cl2 (1 mol %), B (2 mol %) and a magnetic stir bar were placed in the tube, followed by addition of arylboronic acid (1 mmol), NaHCO3 (2 mmol), 1,4-dioxane (2 mL) and water (0.5 mL). the tube was capped with a stopper. The autoclave was cooled down to -100 °C by liquid nitrogen, and 2-chloro-3,3,3-trifluoroprop-1-ene (2, 18 mmol) was added to the reaction. Finally the autoclave was heated in an oil bath at 100 °C for 5 h. After the reaction, the autoclave was then cooled to room temperature and vented to discharge the excessive 2,3,3,3-tetrafluoropropylene carefully. Water (60 mL) was added, and the product was extracted with dichloromethane (3*15 mL). The organic layers were washed with brine (30 mL), dried over Na2SO4, and the organic solvent was evaporated by a rotary evaporator under atmospheric pressure. The crude product was purified by column chromatography (silica gel, petroleum ether/ethyl acetate as eluents). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water at 40 - 80℃; for 12h; Inert atmosphere; | 2.2 Synthesis of 5-(5-chloro-2-nitrophenyl)-1-phenyl-1H-indole Nitrogen gas stream under the above obtained from 5-bromo-1-phenyl-1H-indole (20 g, 73.49 mmol), 5-chloro-2-nitrophenylboronic acid (17.78g, 88.18 mmol), K 2 CO 3 (30.47 g, 220.47 mmol) and THF / H2O into the (400ml / 100 ml) was stirred. In 40 °C Pd(PPh3)4 into the (2.54 g, 2.204mmol) it was stirred under reflux at 80 °C for 12 hours.After completion of the reaction extracted with dichloromethane, and the organic layer is MgSO4was filtered off and dried in a vacuum.The filtered organic layer was evaporated under reduced pressure to a back by column chromatography the desired compound 5- (5-chloro-2- nitrophenyl) -1-phenyl-1H-indole (18 g,yield: 72%) was obtained. |
72% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water at 40 - 80℃; for 12h; Inert atmosphere; | 1.1 Synthesis of 5-(5-chloro-2-nitrophenyl)-1-phenyl-1H-indole A stream of nitrogen under 5-bromo-1-phenyl-1H-indole (20 g, 73.49 mmol), 5-chloro-2-nitrophenylboronic acid (17.78g, 88.18 mmol), K2CO3 (30.47 g, 220.47 mmol) and THF/H2O (400ml / 100 ml) were put into a stirred. At 40 into the Pd (PPh3) 4 (2.54 g, 2.204mmol) was stirred under reflux at 80 for 12 hours. After completion of the reaction, which was then extracted with dichloromethane. The organic layer was dried over MgSO4 filtered under reduced pressure. The filtered organic layer was evaporated under reduced pressure to a back by column chromatography the desired compound 5- (5-chloro-2-nitrophenyl) -1-phenyl-1H-indole (18g, Yield: 72%) was obtained. |
72% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water at 80℃; for 12h; | 2.2 Step 2 Synthesis of 5- (5-chloro-2-nitrophenyl) -1-phenyl-1H-indole 20 g, 73.49 mmol), 5-chloro-2-nitrophenylboronic acid (17.78 g, 88.18 mmol), K2CO3 (30.47 g, 220.47 mmol) and THF / H2O (400 ml / 100 ml) was added and stirred. At 40 ° CPd (PPh3) 4 (2.54 g, 2.204 mmol) was added and the mixture was refluxed and stirred at 80 for 12 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane. The organic layer was dried over MgSO4 and filtered under reduced pressure. The filtrated organic layer was distilled under reduced pressure, and then the target compound, 5- (5-chloro-2-nitrophenyl) -1-phenyl-1H-indole (18 g, yield: 72%) was obtained by column chromatography |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / tetrahydrofuran; water / 12 h / 40 - 80 °C / Inert atmosphere 2: triphenylphosphine / 1,2-dichloro-benzene / 12 h / Inert atmosphere | ||
Multi-step reaction with 2 steps 1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran; water / 12 h / 40 - 80 °C / Inert atmosphere 2: triphenylphosphine / 1,2-dichloro-benzene / 12 h / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / tetrahydrofuran; water / 12 h / 40 - 80 °C / Inert atmosphere 2: triphenylphosphine / 1,2-dichloro-benzene / 12 h / Inert atmosphere 3: tetrakis(triphenylphosphine) palladium(0); sodium hydroxide / tetrahydrofuran; water / 12 h / 40 - 80 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / tetrahydrofuran; water / 12 h / 40 - 80 °C / Inert atmosphere 2: triphenylphosphine / 1,2-dichloro-benzene / 12 h / Inert atmosphere 3: tetrakis(triphenylphosphine) palladium(0); sodium hydroxide / tetrahydrofuran; water / 12 h / 40 - 80 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene at 110℃; for 3h; Inert atmosphere; | 4.3 <Step 3> Synthesis of D1 Under a nitrogen stream A2, 3.7g, (10.8 mmol), 5-chloro-2-nitrophenylboronic acid, 2.2g (10.8 mmol), 0.6g (5 mol%) of Pd (PPh3) 4, and potassium carbonate, 4.5g ( put Toluene / H2O / Ethanol of 32.3 mmol) and 80ml / 40ml / 40ml was stirred for 3 hours at 110 °C. After the reaction, using a methylene chloride The organic layer was separated using MgSO4 was removed [0182] water. The solvent of the organic layer was purified by column chromatography to give the title compound, D1, (3.7g, 8,7mmol, yield 81%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran; water / 12 h / 40 - 80 °C / Inert atmosphere 2: triphenylphosphine / 1,2-dichloro-benzene / 12 h / Inert atmosphere 3: copper; potassium carbonate / nitrobenzene / 24 h / Inert atmosphere; Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran; water / 12 h / 40 - 80 °C / Inert atmosphere 2: triphenylphosphine / 1,2-dichloro-benzene / 12 h / Inert atmosphere 3: copper; potassium carbonate / nitrobenzene / 24 h / Inert atmosphere; Reflux 4: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran; water / 12 h / 40 - 80 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran; water / 12 h / 40 - 80 °C / Inert atmosphere 2: triphenylphosphine / 1,2-dichloro-benzene / 12 h / Inert atmosphere 3: copper; potassium carbonate / nitrobenzene / 24 h / Inert atmosphere; Reflux 4: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 12 h / Inert atmosphere; Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran; water / 12 h / 40 - 80 °C / Inert atmosphere 2: triphenylphosphine / 1,2-dichloro-benzene / 12 h / Inert atmosphere 3: copper; potassium carbonate / nitrobenzene / 24 h / Inert atmosphere; Reflux 4: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran; water / 12 h / 40 - 80 °C / Inert atmosphere 5: copper; sodium sulfate; potassium carbonate / nitrobenzene / 12 h / 190 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate In tetrahydrofuran; water at 100 - 120℃; for 2h; Microwave irradiation; | 1.1 Step 1: ethyl 3-(5-chloro-2-nitrophenyl)-6,7-dihydro-5H-cyclopenta[b]pyridine-7-carboxylate Step 1: Ethyl 3 (5chloro2nitrophenyl (1C)A microwave vial was charged with ethyl 3 bromo-6, 7dihydro5Wcyclopenta[bipyridine7 carboxylate (1A) (1.0 g, 3.7 rnmol), (5-cliloro.-2-nitrophenyi)boronic acid (i-B) (1.49 g, 7.40 mmol), 1,1’ -.bis(diphenylphosphino)ferrocene-.palladiumll)di chloride di chloromethane complex (0.605 g, 0.740 mmol), THF (5 mL), and 2M aq. potassium phosphate tribasic (7.4 mL, 14.8 mmol). The reaction mixture ‘as heated at 100°C under microwave irradiation for 60 mm Afterthis time, the reaction was not complete by LCMS analysis. More (5chloro-.2- nitrophenyi)boronic acid (1491 g, 7.40 mmoi) was added, and the reaction mixture was heated at 120°C for 60 mm. The mixture was cooled, filtered through celite, and the filtrates were partitioned between EtOAc and water. The organic phase was washed with brine, dried over sodium sulfate, and concentrated. Flash chromatography (80g Si02, 0-400% EtOAc in hexane)gave the title compound. MS (ESI) rn/z 349.22 (M±H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | With sodium carbonate In toluene at 75 - 90℃; Inert atmosphere; | 1.2 (2) A 1 liter three-necked flask equipped with magnetic stirring. After nitrogen replacement, 20.35g (0.189mol) of sodium carbonate, 24.5g (0.1mol) of (5-chloro-2-nitrophenyl)boronic acid and 100ml of toluene were added in sequence. After replacing with nitrogen again, 5 g (7 mmol) of Pd132 were sequentially added. After the addition, heat to 80°C. Begin to add dropwise to the solution consisting of 27.39g of compound P1-1 (0.11mol) and 100ml of toluene, and the temperature was controlled at 75-90°C. After the reaction, the organic phase was separated, extracted, dried, column chromatography, and the solvent was spin-dried to obtain 25.02 g of yellow solid P1-2 with a yield of 77%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / 1,4-dioxane; water / 12 h / 90 °C / Inert atmosphere 2: triethyl phosphite / 145 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / 1,4-dioxane; water / 12 h / 90 °C / Inert atmosphere 2: triethyl phosphite / 145 °C / Inert atmosphere 3: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / 1,4-dioxane; water / 12 h / 80 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / 1,4-dioxane; water / 12 h / 90 °C / Inert atmosphere 2: triethyl phosphite / 145 °C / Inert atmosphere 3: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / 1,4-dioxane; water / 12 h / 80 °C / Inert atmosphere 4: tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; potassium <i>tert</i>-butylate / o-xylene / 12 h / 120 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 90℃; for 12h; Inert atmosphere; | 6.1 (1) Synthesis of intermediate 325-1 Add the intermediate 2-bromodibenzo[b,e][1,4]dioxin (16.15g, 61.4mmol), 295-2 (12.36g, 61.4mmol), into a 500mL reaction flask, tetrakis(triphenylphosphine)palladium (5mol%), K2CO3 (17.0g, 122.8mmol), 1,4-dioxane (200mL) and water (50mL). The reaction system was heated to 90 °C and reacted for 12 hours under the protection of nitrogen. After the completion of the reaction, the reaction solution was cooled to room temperature and extracted with o-dichlorobenzene and water. The organic layer was dried with anhydrous magnesium sulfate, concentrated and recrystallized, and the crude product obtained was passed through a silica gel column to obtain Intermediate 325-1 (13.56 g, yield 65%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 90℃; for 12h; Inert atmosphere; | 1.2 (2) Synthesis of Intermediate 295-3 Intermediate 295-1 (21.44g, 61.4mmol), 295-2 (12.36g, 61.4mmol), tetrakis(triphenylphosphine)palladium (5mol%) were added to a 500mL reaction flask, K2CO3 (17.0 g, 122.8 mmol), 1,4-dioxane (200 mL) and water (50 mL). The reaction system was heated to 90 °C and reacted for 12 hours under nitrogen protection. After the completion of the reaction, the reaction solution was cooled to room temperature and extracted with o-dichlorobenzene and water. The organic layer was dried with anhydrous magnesium sulfate, concentrated, and the crude product obtained by recrystallization was passed through a silica gel column to obtain Intermediate 295-3 (18.30 g, yield 70%). |
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