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CAS No. : | 343864-78-8 | MDL No. : | MFCD18391759 |
Formula : | C6H3BrINO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | VWDMDPDGACOPSR-UHFFFAOYSA-N |
M.W : | 327.90 | Pubchem ID : | 12700217 |
Synonyms : |
|
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 55.68 |
TPSA : | 45.82 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | Yes |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.11 cm/s |
Log Po/w (iLOGP) : | 1.86 |
Log Po/w (XLOGP3) : | 3.09 |
Log Po/w (WLOGP) : | 2.96 |
Log Po/w (MLOGP) : | 3.35 |
Log Po/w (SILICOS-IT) : | 1.35 |
Consensus Log Po/w : | 2.52 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -4.16 |
Solubility : | 0.0228 mg/ml ; 0.0000696 mol/l |
Class : | Moderately soluble |
Log S (Ali) : | -3.72 |
Solubility : | 0.0625 mg/ml ; 0.000191 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.55 |
Solubility : | 0.0916 mg/ml ; 0.000279 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 3.0 alert |
Leadlikeness : | 0.0 |
Synthetic accessibility : | 2.3 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With copper |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With copper |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | In a nitrogen atmosphere, <strong>[5228-61-5]5-bromo-2-nitroaniline</strong> (122 grams (g), 562 millimoles, mmol), H2SO4 (122 milliliters, ml), and pure water (3.1 liters, L) were mixed and cooled to a temperature of 0 C., and an aqueous solution (620 ml) of NaNO2 (42.7 g, 619 mmol, 1.1 eq) was added dropwise thereto for 1 hour and stirred at room temperature for 3 hours. A reaction solution was cooled to a temperature of 0 C., an aqueous solution (620 ml) of KI (117 g, 705 mmol, 1.25 equivalents, eq) was added dropwise thereto for 1 hour, and Cu powder (1.07 g, 16.8 mmol, 0.03 eq) was added. The reaction solution was stirred at a temperature of 70 C. for 3 hours. The reaction solution was cooled to room temperature, and an organic layer was extracted therefrom by using CH2Cl2. The organic layer was washed with a 10% Na2S2O3 aqueous solution, dried by using anhydrous magnesium sulfate, filtered, and then concentrated. The resultant obtained therefrom was purified by silica gel chromatography (hexane:CH2Cl2=5:1 as developing solvent) to provide Compound 14-1 that was a yellow solid. 116.1 g of Compound 14-1 was obtained, and the yield of Compound 14-1 was 63%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
56% | With copper(l) iodide; bis(benzonitrile)palladium(II) dichloride; triphenyl-arsane In 1-methyl-pyrrolidin-2-one at 80℃; for 48h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 56 percent / PdCl2(PhCN)2; Ph3As; CuI / 1-methyl-pyrrolidin-2-one / 48 h / 80 °C 2: 52 percent / CO; dppp; 1,10-phenanthroline monohydrate / Pd(dba)2 / dimethylformamide / 192 h / 80 °C / 4560 Torr |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: copper-powder 2: fuming nitric acid |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: copper-powder 2: concentrated H2SO4 / <2 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: copper-powder 2: concentrated H2SO4 / <2 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: copper-powder 2: concentrated H2SO4 / <2 3: concentrated H2SO4; HNO3 / 100 °C | ||
Multi-step reaction with 3 steps 1: copper-powder 2: concentrated H2SO4 / <2 3: concentrated H2SO4; HNO3 / 100 °C | ||
Multi-step reaction with 2 steps 1: copper-powder 2: concentrated H2SO4; HNO3 / 100 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | With tetrakis-(triphenylphosphine)-palladium; tetrabutylammonium bromide; anhydrous sodium carbonate In ethanol; water monomer; toluene for 16h; Inert atmosphere; Reflux; | 4 Intermediate Synthesis Example 4 Under a nitrogen atmosphere, 4-bromo-2-iodonitrobenzene (34.43g, 105mmol), 1-naphthalene boronic acid (17.20g, 100mmol) were successively added to the 1000mL there-necked flask,Tetrakis(triphenylphosphine)palladium (Pd(PPh3)4, 1.15 g, 1 mmol),Tetrabutylammonium bromide (TBAB, 3.22 g, 10 mmol), anhydrous sodium carbonate (Na2CO3, 21.20 g, 200 mmol), toluene (PhMe, 360 mL) and deionized water (90 mL),Turn on stirring and heating, and heat up to reflux for 16h. After the system was cooled to room temperature,Extract with dichloromethane (150mL×3 times),The organic phase was dried with anhydrous magnesium sulfate, filtered, and the solvent was distilled off under reduced pressure.Get crude.The crude product was purified by silica gel column chromatography using n-heptane/dichloromethane as mobile phase,A yellow solid intermediate Sub-e1 (27.24 g, 83% yield) was obtained. |
72% | With tetrakis-(triphenylphosphine)-palladium; potassium carbonate In tetrahydrofuran; water monomer at 70℃; | 1.1 Synthesis of Sub 2-I-13 Is the starting material a naphthalen-1-ylboronic acid (79.53 g, 462.40 mmol) and 4-bromo-2-iodo-1-nitrobenzene (227.44 g, 693.60 mmol) for in round bottom flask THF (1500 ml) and water (750 ml) to senses a rotation velocity of the disk to, K2CO3(191.73 g, 1387.20 mmol), Pd (PPh3)4(26.72 g, 23.10 mmol) adding an 70 °C stirring section. When reaction is completed CH2Cl2and a water extraction of organic layer after MgSO4to dry a silicagel column with a compound formed after the products and recrystallization obtained a 109.26 g (yield: 72%) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / water; tetrahydrofuran / 70 °C 2: triphenylphosphine / 1,2-dichloro-benzene / 200 °C 3: tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate; tri-tert-butyl phosphine / toluene / 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / water; tetrahydrofuran / 70 °C 2: triphenylphosphine / 1,2-dichloro-benzene / 200 °C 3: tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate; tri-tert-butyl phosphine / toluene / 80 °C 4: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / N,N-dimethyl-formamide / 90 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / water; tetrahydrofuran / 70 °C 2: triphenylphosphine / 1,2-dichloro-benzene / 200 °C 3: tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate; tri-tert-butyl phosphine / toluene / 80 °C 4: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / N,N-dimethyl-formamide / 90 °C 5: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / water; tetrahydrofuran / 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / water; tetrahydrofuran / 70 °C 2: triphenylphosphine / 1,2-dichloro-benzene / 200 °C 3: tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate; tri-tert-butyl phosphine / toluene / 80 °C 4: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / N,N-dimethyl-formamide / 90 °C 5: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / water; tetrahydrofuran / 80 °C 6: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / N,N-dimethyl-formamide / 90 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 120℃; for 4h; Inert atmosphere; | 5.4 Synthesis of 6- (5-bromo-2-nitrophenyl) -2-phenylbenzo [d] thiazole A stream of nitrogen 2-phenyl-6- (4,4,5,5- tetramethyl-1,3,2-dioxaborolan-2-yl) benzo [d] thiazole (140.2 g, 415.7 mmol), 4-bromo-2-iodo-1-nitrobenzene (150.0 g, 457.4 mmol), Pd (PPh 3) 4 (24.0 g, 20.8 mmol), K 2 CO 3 (143.7 g, 1.04 mol), 1,4-dioxane / H 2 O (mixing 400 ml / 100 ml) and stirred for 4 hours at 120 . [274]After completion of the reaction, extraction with methylene chloride and MgSO4and filtered into a.After removal of the solvent from the obtained organic layer was purified by column chromatography (Hexane: EA = 7: 1 (v / v))to give 6- (5-bromo-2- nitrophenyl) -2-phenylbenzo [d] thiazole (143.5 ga, to give a 84% yield).[275]1H-NMR: δ7.41 (t, 1H), 7.51 (dd, 2H), 7.72 (s, 1H), 7.77 (d, 1H), 7.81 (d, 1H), 7.98 (d, 1H), 8.03 (d, 2H), 8.21 (d, 1H), 8.34 (s, 1H) |
84% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 120℃; for 4h; Inert atmosphere; | 9.1 Synthesis of 6- (5-bromo-2-nitrophenyl) -2-phenylbenzo [d] thiazole Preparation of Example 8 in a nitrogen stream 2-phenyl-6- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) obtained from benzo [d] thiazole (140.2 g , 415.7 mmol), 4-bromo-2-iodo-1-nitrobenzene (150.0 g, 457.4 mmol), Pd (PPh3) 4 (24.0 g, 20.8 mmol), K2CO3 (143.7 g, 1.04 mol), 1,4 - mixing a dioxane / H2O (400 ml / 100 ml) and stirred for 4 hours at 120 °C. After the reaction was terminated by extraction with methylene chloride and the MgSO4, insert, and then filtered. After removal of the solvent from the obtained organic layer was purified by column chromatography (Hexane: EA = 7: 1 (v / v)) to give 6- (5-bromo-2-nitrophenyl) -2-phenylbenzo [d] thiazole (143.5 g a, to give a 84% yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 120℃; for 4h; Inert atmosphere; | 1.4 Synthesis of 6- (5-bromo-2-nitrophenyl) -2-phenylbenzo [d] oxazole A stream of nitrogen 2-phenyl-6- (4,4,5,5- tetramethyl-1,3,2-dioxaborolan-2-yl) benzo [d] oxazole (133.5 g, 415.8 mmol), 4-bromo-2-iodo-1-nitrobenzene (150.0 g, 457.4 mmol), Pd (PPh 3) 4 (24.0 g, 20.8 mmol), K 2 CO 3 (143.7 g, 1.04 mol), 1,4-dioxane / H 2 O (mixing 400 ml / 100 ml) and stirred for 4 hours at 120 . [138]After completion of the reaction, extraction with methylene chloride and MgSO4and filtered into a.After removal of the solvent from the obtained organic layer was purified by column chromatography (Hexane: EA = 8: 1 (v / v))to give 6- (5-bromo-2- nitrophenyl) -2-phenylbenzo [d] oxazole (138 g, the to give a 84% yield).[139]1H-NMR: δ7.41 (t, 1H) 7.48 (s, 1H), 7.51 (dd, 2H), 7.68 (d, 1H), 7.72 (s, 1H), 7.79 (d, 1H), 7.98 (d, 1H), 8.05 (d, 2H), 8.21 (d, 1H) |
84% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 120℃; for 4h; Inert atmosphere; | 20.1 Synthesis of 6-(5-bromo-2-nitrophenyl)-2-phenylbenzo[d]oxazole A stream of nitrogen 2-phenyl-6- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benz[d]oxazole (133.5 g, 415.8 mmol), 4-bromo-2-iodo-1-nitrobenzene (150.0 g, 457.4 mmol), Pd(PPh3) 4 (24.0 g, 20.8 mmol), K2CO3 (143.7 g, 1.04 mol), 1,4-dioxane/ H2O (400 ml/100 ml) and the mixture was stirred for 4 hours at 120°C . After the reaction was terminated by extraction with methylene chloride, filtered, put MgSO4. After removal of the solvent from the obtained organic layer was purified by column chromatography (Hexane: EA = 8: 1 (v / v)) to give 6-(5-bromo-2-nitrophenyl)-2-phenylbenzo[d]oxazole (138 g, to give a 84% yield). |
84% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 120℃; for 4h; Inert atmosphere; | 2.1 Synthesis of 6-(5-bromo-2-nitrophenyl)-2-phenylbenzo[d]oxazole 2-phenyl-6- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) obtained in of Example 1 prepared under the flow of nitrogen benzo [d] oxazole (133.5 g , 415.8 mmol), 4-bromo-2-iodo-1-nitrobenzene (150.0 g, 457.4 mmol), Pd (PPh3) 4 (24.0 g, 20.8 mmol), K2CO3 (143.7 g, 1.04 mol), 1,4 - mixing a dioxane / H2O (400 ml / 100 ml) and stirred for between 4 h 120 °. After the reaction was terminated by extraction with methylene chloride, filtered, put MgSO4. After removal of the solvent from the obtained organic layer was purified by column chromatography (Hexane: EA = 8: 1 (v / v)) to give 6- (5-bromo-2-nitrophenyl) -2-phenylbenzo [d] oxazole (138 g, the to give a 84% yield) |
75% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 80℃; for 12h; Inert atmosphere; | 1 1, Synthesis of intermediate 1-1-1 To 500 milliliters reaction flask were added intermediate 1-1 (19.72 dag, 61.4 mmol), 4 - bromo -2 - iod -1 - nitrobenzene (20.07 dag, 61.4 mmol), tetrakis (triphenylphosphine) palladium (5 mol %), K2CO3 (17.0 dag, 122.8 mmol), dioxane (1,4 -) and water (200 milliliters). The reaction system was heated to 50 milliliters and nitrogen was protected to react 80 (degree) C 12 hours. After completion of the reaction, the reaction solution was cooled to room temperature and extracted with o-dichlorobenzene and water. The organic layer was dried over anhydrous magnesium sulfate, concentrated and recrystallized to obtain an intermediate 1-1-1 (18.20 dag, yield 75%). |
68% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water at 80℃; for 12h; | Example 1 Of Preparation Example 1 under nitrogen gas stream obtained in 2-phenyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]oxazole (149.48 g, 0.465 mol), 4-bromo-2-iodo-1-nitrobenzene (138.73 g, 0.423 mol),Pd(PPh3)4 (24.45 g, 21.15 mmol), K2CO3 (175.43 g, 1.27 mol), THF/H2O (2000 ml/1000 ml) and the mixture , 80 In was stirred for 12 hours . After completion of the reaction, the organic layer was extracted with methylene chloride , filtered, put MgSO4. The solvent in the resulting organic layerAfter removal of the column chromatography (Hexane: EA = 8: 1 (v / v)) to give 6-(5-bromo-2-nitrophenyl)-2-phenylbenzo[d]oxazole to give the ( 113.7 g , 68% yield). |
68% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water at 80℃; for 12h; Inert atmosphere; | 1.4 Synthesis of 6-(5-bromo-2-nitrophenyl)-2-phenylbenzo[d]oxazole A stream of nitrogen 2-phenyl-6- (4,4,5,5- tetramethyl-1,3,2-dioxaborolan-2-yl) benzo [d] oxazole (149.48 g, 0.465 mol), 4-bromo-2-iodo-1-nitrobenzene (138.73 g, 0.423 mol), Pd (PPh 3) 4 (24.45 g, 21.15 mmol), K 2 CO 3 (175.43 g, 1.27 mol), THF / H 2 O (2000 ml/1000mixing ml) and stirred for 12 hours at 80 .After the reaction was terminated by extraction with methylene chloride and MgSO4and filtered into a.After removal of the solvent from the obtained organic layer was purified by column chromatography (Hexane: EA = 8: 1 (v / v))to give 6- (5-bromo-2- nitrophenyl) -2-phenylbenzo [d] oxazole (113.7 ga, with a yield of 68%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With tetrakis(triphenylphosphine) palladium(0); sodium hydroxide In tetrahydrofuran; water at 80℃; | 1.1 (1) Sub-1-I-1 Synthesis The starting material, phenylboronic acid(38.3 g, 314.1 mmol) to a round bottom flask was charged with THF (1152ml) todissolve later, 4-bromo-2-iodo-1-nitrobenzene (123.6 g, 376.9 mmol), Pd(PPh3)4( 18.15 g, 15.7 mmol), NaOH (37.69 g, 942.3 mmol), water (576ml) was added andthe mixture was stirred at 80 . It was obtained:When the reaction is complete, the organic layer was dried and extracted withwater and CH2Cl2 over MgSO4, concentrated and recrystallized silicagel column product 66.39 g (76% yield) and the resulting compound then |
73% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water at 80℃; for 24h; | Synthesis of intermediate F 4-bromo-2-iodo-1-nitrobenzene and after the injection by phenylboronic acid dissolved in 1mol and THF, respectively, Pd (PPh3) 4, 2MK2CO3, respectively, into water and stirred at 80°C and refluxed for 24 hours. When the reaction is finished the temperature of the reaction to room temperature, Cooled, CH2Cl2 and chromatography of the product produced and the organic layer was dried over anhydrous MgSO4, concentrated and extracted with water, the column Blood and recrystallization to obtain the desired intermediate F (yield: 73%). |
71% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran Inert atmosphere; Reflux; | Synthesis of intermediate F Under nitrogen atmosphere, 4-bromo-2-iodo-1-nitrobenzene 3.28g (10mmol), phenylboronic acid 1.22g (10mmol) were dissolved in THF 25ml, Pd(PPh3)4 0.58g (0.5mmol), 2M K2CO3 15ml (30mmol) was added and refluxed for 24 hours. After completion of the reaction, MC 200ml, H2O 200ml was added and then the the MC layer was extracted, concentrated and separated by column chromatography using Hex : EA =5 : 1 and dried over anhydrous MgSO4 to give the intermediate F 1.97g (71%). |
71% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran for 24h; Inert atmosphere; Reflux; | Synthesis of Intermediate E After injecting 4-bromo-2-iodo-1-nitrobenzene 3.28g (10mmol) and phenylboronic acid 1.22g(10mmol) dissolved in THF 25ml under nitrogen, Pd (PPh3) 4 0.58g (0.5mmol) and 2M K2CO3 15ml (30mmol) were added and refluxed for 24 hours. After completion of the reaction, MC 200ml and 200ml H2O were added, MC layer was extracted, and dried over anhydrous MgSO4 and concentrated by column with Hex: EA = 5: 1 to give 1.97g of intermediate E (71%). |
71% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran for 24h; Inert atmosphere; Reflux; | 1 synthesis of Intermediate B After injecting 4-bromo-2-iodo-1-nitrobenzene, 3.28g (10mmol) and phenylboronic acid 1.22g (10mmol) under nitrogen and dissolved in THF25ml, Pd (PPh3) 4 0.58g (0.5mmol), by the addition of 15ml 2M K2CO3 (30mmol) it was refluxed for 24 hoursWhen the reaction is complete, cool the temperature of the reaction to room temperature, 200ml MC, was added 200ml of H2O and extract the MC layer, and then the organic layer was evaporated under reduced pressure to Hex: MC = 5: 1 Intermediate B 1.97g (71%) to the column at a obtained |
71% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran for 24h; Inert atmosphere; Reflux; | Synthesis of Intermediate 26 Synthesis of Intermediate 26 (0162) (0163) Under a nitrogen atmosphere, 4-bromo-2-iodo-1-nitrobenzene (3.28 g, 10 mmol) and phenylboronic acid (1.22 g, 10 mmol) were mixed and dissolved in tetrahydrofuran (25 mL) Then Pd(PPh3)4 (0.58 g, 0.5 mmol) and K2CO3 (2 M, 15 mL, 30 mmol) were added and refluxed for 24 hrs. (0164) After the reaction was terminated, MC (200 mL) and H2O (200 mL) were added. The MC layer was extracted, dried over anhydrous magnesium sulfate, concentrated, and purified by column chromatography eluting with Hex:MC=5:1, to obtain Intermediate 26 (1.97 g, 71%). (0165) Intermediate 26 MS(FAB): 278(M+) |
71% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran for 24h; Inert atmosphere; Reflux; | 1 Synthesis of Intermediate 22 Under a nitrogen atmosphere, 4-bromo-2-iodo-1-nitrobenzene (3.28 g, 10 mmol) and phenylboronic acid (1.22 g, 10 mmol) were mixed and dissolved in tetrahydrofuran (25 mL). Pd(PPh3)4 (0.58 g, 0.5 mmol) and K2CO3 (2 M, 30 mmol, 15 mL) were added and refluxed for 24 hrs. After the reaction was terminated, MC (200 mL) and H2O (200 mL) were added. The MC layer was extracted, dried over anhydrous magnesium sulfate, concentrated, and purified by column chromatography eluting with Hex:MC=5:1, to obtain Intermediate 22 (1.97 g, 71%). Intermediate 22 MS(FAB): 278(M+) |
70% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water at 80℃; | 1.3 Sub 1-I-1 synthesis Is the starting material a phenylboronic acid (105.55g, 865.7mmol) senses a rotation velocity of the disk to a in round bottom flask THF to, 4-bromo-2-iodo-1-nitrobenzene (425.78g, 1298.5mmol), Pd (PPh 3) 4 (50.02g, 43.3mmol), K 2 CO 3 (358.93g, 2597mmol), water are added 80 °C stirring section. When reaction is completed CH 2 Cl 2 and a water extraction of organic layer after MgSO 4 to dry a silicagel column with a compound formed after the products and recrystallization 168.52g (yield: 70%)is obtained. |
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water at 80℃; | 1.1 (1) Sub 1-1 synthesis example General procedure: After dissolving phenylboronic acid (1 eq.) in a round bottom flask with THF, 1-iodo-2-nitrobenzen substituted with Br (1.1 eq), Pd(PPh3)4 (0.05 equivalent), K2CO3 (3 equivalents), Water was added and stirred at 80 °C. After that, After the reaction was completed, extracted with CH2Cl2 and water, the organic layer was dried over MgSO4, concentrated, and the resulting compound was silicagel column and recrystallized to obtain Sub 1-1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / tetrahydrofuran; water / 80 °C 2: triphenylphosphine / 1,2-dichloro-benzene / 200 °C | ||
Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium(0); sodium hydroxide / tetrahydrofuran; water / 80 °C 2: triphenylphosphine / 1,2-dichloro-benzene / 200 °C | ||
Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / tetrahydrofuran; water / 24 h / 80 °C 2: triphenylphosphine / 1,2-dichloro-benzene / 200 °C |
Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / tetrahydrofuran / Inert atmosphere; Reflux 2: triphenylphosphine / 1,2-dichloro-benzene / Inert atmosphere; Reflux | ||
Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / tetrahydrofuran / 24 h / Inert atmosphere; Reflux 2: triphenylphosphine / 1,2-dichloro-benzene / Inert atmosphere; Reflux | ||
Multi-step reaction with 2 steps 1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran / 24 h / Inert atmosphere; Reflux 2: triphenylphosphine / 1,2-dichloro-benzene / Inert atmosphere; Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / tetrahydrofuran; water / 80 °C 2: triphenylphosphine / 1,2-dichloro-benzene / 200 °C 3: potassium carbonate; sodium sulfate; copper / nitrobenzene / 200 °C | ||
Multi-step reaction with 3 steps 1: tetrakis(triphenylphosphine) palladium(0); sodium hydroxide / tetrahydrofuran; water / 80 °C 2: triphenylphosphine / 1,2-dichloro-benzene / 200 °C 3: sodium sulfate; potassium carbonate; copper / nitrobenzene / 200 °C | ||
Multi-step reaction with 3 steps 1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / tetrahydrofuran; water / 24 h / 80 °C 2: triphenylphosphine / 1,2-dichloro-benzene / 200 °C 3: potassium carbonate; sodium sulfate; copper / nitrobenzene / 200 °C |
Multi-step reaction with 3 steps 1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / tetrahydrofuran / Inert atmosphere; Reflux 2: triphenylphosphine / 1,2-dichloro-benzene / Inert atmosphere; Reflux 3: potassium carbonate; copper / nitrobenzene / 16 h / Inert atmosphere; Reflux | ||
Multi-step reaction with 3 steps 1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran / 24 h / Inert atmosphere; Reflux 2: triphenylphosphine / 1,2-dichloro-benzene / Inert atmosphere; Reflux 3: potassium carbonate; copper / nitrobenzene / 16 h / Inert atmosphere; Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / tetrahydrofuran; water / 80 °C 2: triphenylphosphine / 1,2-dichloro-benzene / 200 °C 3: potassium carbonate; sodium sulfate; copper / nitrobenzene / 200 °C 4: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / N,N-dimethyl-formamide / 90 °C | ||
Multi-step reaction with 4 steps 1: tetrakis(triphenylphosphine) palladium(0); sodium hydroxide / tetrahydrofuran; water / 80 °C 2: triphenylphosphine / 1,2-dichloro-benzene / 200 °C 3: sodium sulfate; potassium carbonate; copper / nitrobenzene / 200 °C 4: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / N,N-dimethyl-formamide / 90 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / tetrahydrofuran; water / 80 °C 2: triphenylphosphine / 1,2-dichloro-benzene / 200 °C 3: potassium carbonate; sodium sulfate; copper / nitrobenzene / 200 °C 4: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / N,N-dimethyl-formamide / 90 °C 5: tetrakis(triphenylphosphine) palladium(0); sodium hydroxide / tetrahydrofuran; water / 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / tetrahydrofuran; water / 80 °C 2: triphenylphosphine / 1,2-dichloro-benzene / 200 °C 3: potassium carbonate; sodium sulfate; copper / nitrobenzene / 200 °C 4: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / N,N-dimethyl-formamide / 90 °C 5: tetrakis(triphenylphosphine) palladium(0); sodium hydroxide / tetrahydrofuran; water / 80 °C 6: tetrakis(triphenylphosphine) palladium(0); sodium hydroxide / tetrahydrofuran; water / 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / tetrahydrofuran; water / 80 °C 2: triphenylphosphine / 1,2-dichloro-benzene / 200 °C 3: potassium carbonate; sodium sulfate; copper / nitrobenzene / 200 °C 4: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / N,N-dimethyl-formamide / 90 °C 5: tetrakis(triphenylphosphine) palladium(0); sodium hydroxide / tetrahydrofuran; water / 80 °C 6: tetrakis(triphenylphosphine) palladium(0); sodium hydroxide / tetrahydrofuran; water / 80 °C 7: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / N,N-dimethyl-formamide / 90 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 8 steps 1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / tetrahydrofuran; water / 80 °C 2: triphenylphosphine / 1,2-dichloro-benzene / 200 °C 3: potassium carbonate; sodium sulfate; copper / nitrobenzene / 200 °C 4: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / N,N-dimethyl-formamide / 90 °C 5: tetrakis(triphenylphosphine) palladium(0); sodium hydroxide / tetrahydrofuran; water / 80 °C 6: tetrakis(triphenylphosphine) palladium(0); sodium hydroxide / tetrahydrofuran; water / 80 °C 7: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / N,N-dimethyl-formamide / 90 °C 8: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / tetrahydrofuran; water / 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 9 steps 1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / tetrahydrofuran; water / 80 °C 2: triphenylphosphine / 1,2-dichloro-benzene / 200 °C 3: potassium carbonate; sodium sulfate; copper / nitrobenzene / 200 °C 4: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / N,N-dimethyl-formamide / 90 °C 5: tetrakis(triphenylphosphine) palladium(0); sodium hydroxide / tetrahydrofuran; water / 80 °C 6: tetrakis(triphenylphosphine) palladium(0); sodium hydroxide / tetrahydrofuran; water / 80 °C 7: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / N,N-dimethyl-formamide / 90 °C 8: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / tetrahydrofuran; water / 80 °C 9: sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine / toluene / 100 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / tetrahydrofuran; water / 80 °C 2: triphenylphosphine / 1,2-dichloro-benzene / 200 °C 3: potassium carbonate; sodium sulfate; copper / nitrobenzene / 200 °C 4: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / N,N-dimethyl-formamide / 90 °C 5: tetrakis(triphenylphosphine) palladium(0); sodium hydroxide / tetrahydrofuran; water / 80 °C 6: tetrakis(triphenylphosphine) palladium(0); sodium hydroxide / tetrahydrofuran; water / 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / tetrahydrofuran; water / 80 °C 2: triphenylphosphine / 1,2-dichloro-benzene / 200 °C 3: potassium carbonate; sodium sulfate; copper / nitrobenzene / 200 °C 4: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / N,N-dimethyl-formamide / 90 °C 5: tetrakis(triphenylphosphine) palladium(0); sodium hydroxide / tetrahydrofuran; water / 80 °C 6: tetrakis(triphenylphosphine) palladium(0); sodium hydroxide / tetrahydrofuran; water / 80 °C 7: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / N,N-dimethyl-formamide / 90 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 120℃; for 4h; Inert atmosphere; | 27.1 Synthesis of 6-(5-bromo-2-nitrophenyl)-2-phenylbenzo[d]thiazole A stream of nitrogen 2-phenyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]thiazole (140.2 g, 415.7 mmol), 4-bromo-2-iodo-1-nitrobenzene (150.0 g, 457.4 mmol), Pd(PPh3)4 (24.0 g, 20.8 mmol), K2CO3 (143.7 g, 1.04 mol), 1,4-dioxane/ H2O (400 ml/100 ml) and the mixture was stirred for 4 hours at 120°C . After the reaction was terminated by extraction with methylene chloride, filtered, put MgSO4. After removal of the solvent from the obtained organic layer was purified by column chromatography (Hexane: EA = 7: 1 (v / v)) to give 6- (5-bromo-2-nitrophenyl)-2-phenylbenzo[d]thiazole(143.5 g 84% yield) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In toluene Reflux; | 3'-1 [3' -1 synthesis] In the round bottom flask, the benzo [b] thiophene-3- base boric acid (benzo[b]thiophen-3-ylboronicacid) 65.1g, 4-bromo-2-iodo-1-nitrobenzene (4-bromo-2-iodo-1-nitrobenzene) 100g dissolving in toluene 1600 ml and adding K2CO3(2M) 455 ml and Pd (PPh3)4(four (triphenylphosphine) palladium) 10.5g of the backflow after stirring. In TLC (thinlayerchromatography, thin layer chromatography) confirmed the reaction and the reaction is terminated after addition of water. The organic layer using EA and extraction (ethanol) of the pressure-reducing filter after the column to purify 87.6g intermediate 3' -1 (the yield is 86%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In toluene Reflux; | 1'-1 [1' -1 synthesis] In the round bottom flask, the benzofuran-3- base boric acid (benzofuran-3-ylboronicacid) 59.3g, 4-bromo-2-iodo-1-nitrobenzene (4-bromo-2-iodo-1-nitrobenzene) 100g dissolving in toluene 1600 ml and adding K2CO3(2M) 450 ml and Pd (PPh3)4(four (triphenylphosphine) palladium) 10.5g of the backflow after stirring. In TLC (thinlayerchromatography, thin layer chromatography) confirmed the reaction and the reaction is terminated after addition of water. The organic layer using EA and extraction (ethanol) of the pressure-reducing filter after the column to purify 82.5g intermediate 1' -1 (the yield is 85%). |
76% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene at 80℃; Inert atmosphere; | 5 Synthesis of intermediate IM-12 In an Ar atmosphere, into a 2,000 mL three-necked flask, 30.00 g (185.2 mmol) of benzofuran-3-ylboronic acid, 66.82 g (1.1 equivalent, 203.8 mmol) of 4-bromo-2-iodo- 1-Nitrobenzene, 76.81g (3.0 equivalent, 555.7mmol) of K2CO3, 10.70g (0.05 equivalent, 9.3mmol) of Pd(PPh3)4 and 1,297mL of toluene/EtOH/H2O (4/2/1) The mixture solution was then heated and stirred at about 80°C. After cooling to room temperature in the air, the reaction solution was extracted with toluene. The aqueous layer was removed, and the organic layer was washed with saturated saline solution and dried with MgSO4. MgSO4 was separated by filtration, and the organic layer was concentrated. The crude product thus obtained was separated by silica gel column chromatography (using a mixed solvent of hexane and toluene as an eluent) to obtain Intermediate IM-12 (44.79 g, yield 76%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / toluene / Reflux 2: triethyl phosphite / 1,2-dichloro-benzene / Reflux | ||
Multi-step reaction with 2 steps 1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / toluene; ethanol; water / 80 °C / Inert atmosphere 2: triethyl phosphite / 1,2-dichloro-benzene / 160 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / toluene / Reflux 2: triethyl phosphite / 1,2-dichloro-benzene / Reflux 3: sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine / toluene / Reflux | ||
Multi-step reaction with 3 steps 1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / toluene; ethanol; water / 80 °C / Inert atmosphere 2: triethyl phosphite / 1,2-dichloro-benzene / 160 °C / Inert atmosphere 3: bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate; tri-tert-butyl phosphine / Inert atmosphere; Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / toluene / Reflux 2: triethyl phosphite / 1,2-dichloro-benzene / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / toluene / Reflux 2: triethyl phosphite / 1,2-dichloro-benzene / Reflux 3: sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine / toluene / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / toluene / Reflux 2: triethyl phosphite / 1,2-dichloro-benzene / Reflux 3: sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine / toluene / Reflux 4: sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine / toluene / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / toluene / Reflux 2: triethyl phosphite / 1,2-dichloro-benzene / Reflux 3: sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine / toluene / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / toluene / Reflux 2: triethyl phosphite / 1,2-dichloro-benzene / Reflux 3: sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine / toluene / Reflux 4: sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine / toluene / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / toluene / Reflux 2: triethyl phosphite / 1,2-dichloro-benzene / Reflux 3: sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine / toluene / Reflux 4: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,4-dioxane / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / toluene / Reflux 2: triethyl phosphite / 1,2-dichloro-benzene / Reflux 3: sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine / toluene / Reflux 4: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane / Reflux | ||
Multi-step reaction with 5 steps 1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / toluene / Reflux 2: triethyl phosphite / 1,2-dichloro-benzene / Reflux 3: sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine / toluene / Reflux 4: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,4-dioxane / Reflux 5: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / toluene / Reflux 2: triethyl phosphite / 1,2-dichloro-benzene / Reflux 3: sodium hydride / N,N-dimethyl-formamide / 12 h / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / toluene / Reflux 2: triethyl phosphite / 1,2-dichloro-benzene / Reflux 3: sodium hydride / N,N-dimethyl-formamide / 12 h / Inert atmosphere 4: sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine / 1,4-dioxane / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / toluene / Reflux 2: triethyl phosphite / 1,2-dichloro-benzene / Reflux 3: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: tetrakis(triphenylphosphine) palladium(0); sodium hydroxide / tetrahydrofuran; water / 80 °C 2: triphenylphosphine / 1,2-dichloro-benzene / 200 °C 3: sodium sulfate; potassium carbonate; copper / nitrobenzene / 200 °C 4: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / N,N-dimethyl-formamide / 90 °C 5: tetrakis(triphenylphosphine) palladium(0); sodium hydroxide / tetrahydrofuran; water / 70 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / tetrahydrofuran; water / 24 h / 80 °C 2.1: triphenylphosphine / 1,2-dichloro-benzene / 200 °C 3.1: potassium carbonate; sodium sulfate; copper / nitrobenzene / 200 °C 4.1: n-butyllithium / tetrahydrofuran / 1 h / -78 - 0 °C 4.2: 12 h / -78 - 20 °C 5.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / tetrahydrofuran / 24 h / Reflux 6.1: tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; potassium <i>tert</i>-butylate / toluene / 2 h / 110 °C 7.1: tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; potassium <i>tert</i>-butylate / toluene / 6 h / 110 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / tetrahydrofuran; water / 24 h / 80 °C 2.1: triphenylphosphine / 1,2-dichloro-benzene / 200 °C 3.1: potassium carbonate; sodium sulfate; copper / nitrobenzene / 200 °C 4.1: n-butyllithium / tetrahydrofuran / 1 h / -78 - 0 °C 4.2: 12 h / -78 - 20 °C 5.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / tetrahydrofuran / 24 h / Reflux 6.1: tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; potassium <i>tert</i>-butylate / toluene / 2 h / 110 °C 7.1: tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; potassium <i>tert</i>-butylate / toluene / 6 h / 110 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / tetrahydrofuran; water / 24 h / 80 °C 2.1: triphenylphosphine / 1,2-dichloro-benzene / 200 °C 3.1: potassium carbonate; sodium sulfate; copper / nitrobenzene / 200 °C 4.1: n-butyllithium / tetrahydrofuran / 1 h / -78 - 0 °C 4.2: 12 h / -78 - 20 °C 5.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / tetrahydrofuran / 24 h / Reflux 6.1: tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; potassium <i>tert</i>-butylate / toluene / 2 h / 110 °C 7.1: tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; potassium <i>tert</i>-butylate / toluene / 6 h / 110 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / tetrahydrofuran; water / 24 h / 80 °C 2.1: triphenylphosphine / 1,2-dichloro-benzene / 200 °C 3.1: potassium carbonate; sodium sulfate; copper / nitrobenzene / 200 °C 4.1: n-butyllithium / tetrahydrofuran / 1 h / -78 - 0 °C 4.2: 12 h / -78 - 20 °C | ||
Multi-step reaction with 4 steps 1.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / tetrahydrofuran / Inert atmosphere; Reflux 2.1: triphenylphosphine / 1,2-dichloro-benzene / Inert atmosphere; Reflux 3.1: potassium carbonate; copper / nitrobenzene / 16 h / Inert atmosphere; Reflux 4.1: n-butyllithium / tetrahydrofuran / 1 h / -78 - 0 °C / Inert atmosphere 4.2: 12 h / -78 - 20 °C / Inert atmosphere | ||
Multi-step reaction with 4 steps 1.1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran / 24 h / Inert atmosphere; Reflux 2.1: triphenylphosphine / 1,2-dichloro-benzene / Inert atmosphere; Reflux 3.1: potassium carbonate; copper / nitrobenzene / 16 h / Inert atmosphere; Reflux 4.1: n-butyllithium / tetrahydrofuran / 1 h / -78 - 0 °C / Inert atmosphere 4.2: 12 h / -78 - 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / tetrahydrofuran; water / 24 h / 80 °C 2.1: triphenylphosphine / 1,2-dichloro-benzene / 200 °C 3.1: potassium carbonate; sodium sulfate; copper / nitrobenzene / 200 °C 4.1: n-butyllithium / tetrahydrofuran / 1 h / -78 - 0 °C 4.2: 12 h / -78 - 20 °C 5.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / tetrahydrofuran / 24 h / Reflux 6.1: tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; potassium <i>tert</i>-butylate / toluene / 2 h / 110 °C | ||
Multi-step reaction with 6 steps 1.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / tetrahydrofuran / Inert atmosphere; Reflux 2.1: triphenylphosphine / 1,2-dichloro-benzene / Inert atmosphere; Reflux 3.1: potassium carbonate; copper / nitrobenzene / 16 h / Inert atmosphere; Reflux 4.1: n-butyllithium / tetrahydrofuran / 1 h / -78 - 0 °C / Inert atmosphere 4.2: 12 h / -78 - 20 °C / Inert atmosphere 5.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / tetrahydrofuran / 24 h / Inert atmosphere; Reflux 6.1: tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate / toluene / 5 h / Inert atmosphere; Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / tetrahydrofuran; water / 24 h / 80 °C 2.1: triphenylphosphine / 1,2-dichloro-benzene / 200 °C 3.1: potassium carbonate; sodium sulfate; copper / nitrobenzene / 200 °C 4.1: n-butyllithium / tetrahydrofuran / 1 h / -78 - 0 °C 4.2: 12 h / -78 - 20 °C 5.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / tetrahydrofuran / 24 h / Reflux 6.1: tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; potassium <i>tert</i>-butylate / toluene / 2 h / 110 °C 7.1: tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; potassium <i>tert</i>-butylate / toluene / 6 h / 110 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / tetrahydrofuran / Inert atmosphere; Reflux 2: triphenylphosphine / 1,2-dichloro-benzene / Inert atmosphere; Reflux 3: potassium carbonate; copper / nitrobenzene / 16 h / Inert atmosphere; Reflux 4: tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate / toluene / 5 h / Inert atmosphere; Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / tetrahydrofuran / Inert atmosphere; Reflux 2.1: triphenylphosphine / 1,2-dichloro-benzene / Inert atmosphere; Reflux 3.1: n-butyllithium / tetrahydrofuran / 1 h / -78 - 0 °C / Inert atmosphere 3.2: 12 h / -78 - 20 °C / Inert atmosphere | ||
Multi-step reaction with 3 steps 1.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / tetrahydrofuran / 24 h / Inert atmosphere; Reflux 2.1: triphenylphosphine / 1,2-dichloro-benzene / Inert atmosphere; Reflux 3.1: n-butyllithium / tetrahydrofuran / 1 h / -78 - 0 °C / Inert atmosphere 3.2: -78 °C 3.3: 0.5 h | ||
Multi-step reaction with 3 steps 1.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / tetrahydrofuran / 24 h / Inert atmosphere; Reflux 2.1: triphenylphosphine / 1,2-dichloro-benzene / Inert atmosphere; Reflux 3.1: n-butyllithium / tetrahydrofuran / 1 h / -78 - 0 °C / Inert atmosphere 3.2: 12 h / -78 °C 3.3: 0.5 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / tetrahydrofuran / Inert atmosphere; Reflux 2.1: triphenylphosphine / 1,2-dichloro-benzene / Inert atmosphere; Reflux 3.1: n-butyllithium / tetrahydrofuran / 1 h / -78 - 0 °C / Inert atmosphere 3.2: 12 h / -78 - 20 °C / Inert atmosphere 4.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / tetrahydrofuran / 24 h / Inert atmosphere; Reflux 5.1: potassium carbonate; copper / nitrobenzene / 16 h / Inert atmosphere; Reflux | ||
Multi-step reaction with 5 steps 1.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / tetrahydrofuran / 24 h / Inert atmosphere; Reflux 2.1: triphenylphosphine / 1,2-dichloro-benzene / Inert atmosphere; Reflux 3.1: n-butyllithium / tetrahydrofuran / 1 h / -78 - 0 °C / Inert atmosphere 3.2: -78 °C 3.3: 0.5 h 4.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / tetrahydrofuran / 24 h / Inert atmosphere; Reflux 5.1: potassium carbonate; copper / nitrobenzene / 16 h / Inert atmosphere; Reflux | ||
Multi-step reaction with 5 steps 1.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / tetrahydrofuran / 24 h / Inert atmosphere; Reflux 2.1: triphenylphosphine / 1,2-dichloro-benzene / Inert atmosphere; Reflux 3.1: n-butyllithium / tetrahydrofuran / 1 h / -78 - 0 °C / Inert atmosphere 3.2: 12 h / -78 °C 3.3: 0.5 h 4.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / tetrahydrofuran / 24 h / Inert atmosphere; Reflux 5.1: potassium carbonate; copper / nitrobenzene / 16 h / Reflux; Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / tetrahydrofuran / Inert atmosphere; Reflux 2: triphenylphosphine / 1,2-dichloro-benzene / Inert atmosphere; Reflux 3: potassium carbonate; copper / nitrobenzene / 16 h / Inert atmosphere; Reflux 4: tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate / toluene / 5 h / Inert atmosphere; Reflux 5: tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate / toluene / 5 h / Inert atmosphere; Reflux | ||
Multi-step reaction with 6 steps 1.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / tetrahydrofuran / Inert atmosphere; Reflux 2.1: triphenylphosphine / 1,2-dichloro-benzene / Inert atmosphere; Reflux 3.1: n-butyllithium / tetrahydrofuran / 1 h / -78 - 0 °C / Inert atmosphere 3.2: 12 h / -78 - 20 °C / Inert atmosphere 4.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / tetrahydrofuran / 24 h / Inert atmosphere; Reflux 5.1: potassium carbonate; copper / nitrobenzene / 16 h / Inert atmosphere; Reflux 6.1: tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate / toluene / 5 h / Inert atmosphere; Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / tetrahydrofuran / 24 h / Inert atmosphere; Reflux 2: triphenylphosphine / 1,2-dichloro-benzene / Inert atmosphere; Reflux 3: potassium carbonate; copper / nitrobenzene / 16 h / Inert atmosphere; Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / tetrahydrofuran / 24 h / Inert atmosphere; Reflux 2.1: triphenylphosphine / 1,2-dichloro-benzene / Inert atmosphere; Reflux 3.1: potassium carbonate; copper / nitrobenzene / 16 h / Inert atmosphere; Reflux 4.1: n-butyllithium / tetrahydrofuran / 1 h / -78 - 0 °C / Inert atmosphere 4.2: 12 h / -78 - 20 °C 4.3: 0.5 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / tetrahydrofuran / 24 h / Inert atmosphere; Reflux 2.1: triphenylphosphine / 1,2-dichloro-benzene / Inert atmosphere; Reflux 3.1: potassium carbonate; copper / nitrobenzene / 16 h / Inert atmosphere; Reflux 4.1: n-butyllithium / tetrahydrofuran / 1 h / -78 - 0 °C / Inert atmosphere 4.2: 12 h / -78 - 20 °C 4.3: 0.5 h 5.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / tetrahydrofuran / 24 h / Inert atmosphere; Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / tetrahydrofuran / 24 h / Inert atmosphere; Reflux 2.1: triphenylphosphine / 1,2-dichloro-benzene / Inert atmosphere; Reflux 3.1: potassium carbonate; copper / nitrobenzene / 16 h / Inert atmosphere; Reflux 4.1: n-butyllithium / tetrahydrofuran / 1 h / -78 - 0 °C / Inert atmosphere 4.2: 12 h / -78 - 20 °C 4.3: 0.5 h 5.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / tetrahydrofuran / 24 h / Inert atmosphere; Reflux 6.1: tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate / toluene / 5 h / Inert atmosphere; Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / tetrahydrofuran / 24 h / Inert atmosphere; Reflux 2.1: triphenylphosphine / 1,2-dichloro-benzene / Inert atmosphere; Reflux 3.1: potassium carbonate; copper / nitrobenzene / 16 h / Inert atmosphere; Reflux 4.1: n-butyllithium / tetrahydrofuran / 1 h / -78 - 0 °C / Inert atmosphere 4.2: 12 h / -78 - 20 °C 4.3: 0.5 h 5.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / tetrahydrofuran / 24 h / Inert atmosphere; Reflux 6.1: tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate / toluene / 5 h / Inert atmosphere; Reflux 7.1: tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate / toluene / 12 h / Inert atmosphere; Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran / 24 h / Inert atmosphere; Reflux 2.1: triphenylphosphine / 1,2-dichloro-benzene / Inert atmosphere; Reflux 3.1: potassium carbonate; copper / nitrobenzene / 16 h / Inert atmosphere; Reflux 4.1: n-butyllithium / tetrahydrofuran / 1 h / -78 - 0 °C / Inert atmosphere 4.2: 12 h / -78 - 20 °C / Inert atmosphere 5.1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran / 24 h / Inert atmosphere; Reflux 6.1: sodium t-butanolate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; palladium diacetate / toluene / 6 h / Inert atmosphere; Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / water; 1,4-dioxane / 20 °C / Inert atmosphere; Reflux 2: triethyl phosphite / Inert atmosphere; Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / water; 1,4-dioxane / 20 °C / Inert atmosphere; Reflux 2: triethyl phosphite / Inert atmosphere; Reflux 3: potassium phosphate; copper(l) iodide; ethylenediamine / toluene / Inert atmosphere; Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,4-dioxane; water; at 20℃;Inert atmosphere; Reflux; | In a nitrogen atmosphere, 40 g (121.98 mmol) of 4-bromo-2-iodo-1-nitrobenzene,21.9 g (146.38 mmol) of the intermediate compound [53-3], 25.2 g (182.97 mmol) of potassium carbonate,4.2 g (3.65 mmol) of tetrakis (triphenylphosphine) palladium,600 ml of 1,4-dioxane, and 60 ml of distilled water.When the reaction was completed, the reaction mixture was cooled to room temperature, and ethyl acetate / distilled waterThe organic layer was separated using anhydrous magnesium sulfate, and then dried and filtered.The filtrate was concentrated under reduced pressure, and then subjected to column chromatography26.1 g (70%) of the intermediate compound [53-4] was synthesized. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1: bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine / 36 h / 20 °C / Inert atmosphere 2: potassium carbonate; methanol / diethyl ether / 2 h / 20 °C / Inert atmosphere 3: bis-triphenylphosphine-palladium(II) chloride / tetrahydrofuran / 36 h / 20 °C / Inert atmosphere 4: copper(l) chloride / N,N-dimethyl-formamide / 3 h / 20 °C / Darkness; Inert atmosphere 5: bis(dibenzylideneacetone)-palladium(0); 1,3-bis-(diphenylphosphino)propane; 1,10-Phenanthroline / N,N-dimethyl-formamide / 60 h / 120 °C / 4560.31 Torr 6: N-Bromosuccinimide / tetrachloromethane / 2 h / 78 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine / 36 h / 20 °C / Inert atmosphere 2: potassium carbonate; methanol / diethyl ether / 2 h / 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine / 36 h / 20 °C / Inert atmosphere 2: potassium carbonate; methanol / diethyl ether / 2 h / 20 °C / Inert atmosphere 3: bis-triphenylphosphine-palladium(II) chloride / tetrahydrofuran / 36 h / 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine / 36 h / 20 °C / Inert atmosphere 2: potassium carbonate; methanol / diethyl ether / 2 h / 20 °C / Inert atmosphere 3: bis-triphenylphosphine-palladium(II) chloride / tetrahydrofuran / 36 h / 20 °C / Inert atmosphere 4: copper(l) chloride / N,N-dimethyl-formamide / 3 h / 20 °C / Darkness; Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 20℃; for 36h; Inert atmosphere; | 2-(5-Bromo-2-nitrophenyl)-1-trimethylsilylethyne (12). To a mixture of 5-bromo-2-nitro-1-iodobenzene (11) (3.50 g, 10.7 mmol), CuI (203 mg, 1.07 mmol) and bis(triphenylphosphine)palladium dichloride (PdCl2(PPh3)2, 374 mg, 0.533 mmol) at ambient temperature under a N2 atmosphere was added (10 mL) followed by the addition of triethylamine (Et3N, 16 mL). After stirring the mixture for 5 minutes, the solution of trimethylsilylethyne (1.40 g, 13.4 mmol) in Et3N (4 mL) was added via syringe. The resulting dark brown mixture was stirred at this temperature for 36 h. The reaction mixture was then filtered through Celite, and the Celite was washed with EtOAc (30 mL). The solvents were removed from the filtrate under reduced pressure. The resulting residue was purified by chromatography (hexane/EtOAc, 95:5) to give 12 (2.93 mg, 9.82 mmol, 92%) as a yellow oil. 1H NMR (600 MHz, CDCl3) δ d, J=8.4 Hz, 1H), 7.79 (d, J=1.8 Hz, 1H), 7.56 (dd, J=8.4, 1.8 Hz, 1H), 0.27 (s, 9H); 13C NMR (150 MHz, CDCl3) δ 148.7, 137.6, 131.9, 127.4, 125.8, 105.7, 98.0, 0.5; IR (ATR) 2958, 1596, 1523, 1341, 1248, 833 cm-1; HRMS (ESI) calcd for C11H13BrNO2Si (M+H+) 297.9899, found 297.9883. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / tetrahydrofuran / 24 h / Inert atmosphere; Reflux 2.1: triphenylphosphine / 1,2-dichloro-benzene / Inert atmosphere; Reflux 3.1: n-butyllithium / tetrahydrofuran / 1 h / -78 - 0 °C / Inert atmosphere 3.2: -78 °C 3.3: 0.5 h 4.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / tetrahydrofuran / 24 h / Inert atmosphere; Reflux 5.1: potassium carbonate; copper / nitrobenzene / 16 h / Inert atmosphere; Reflux 6.1: tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate / toluene / 7 h / Inert atmosphere; Reflux | ||
Multi-step reaction with 6 steps 1.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / tetrahydrofuran / 24 h / Inert atmosphere; Reflux 2.1: triphenylphosphine / 1,2-dichloro-benzene / Inert atmosphere; Reflux 3.1: n-butyllithium / tetrahydrofuran / 1 h / -78 - 0 °C / Inert atmosphere 3.2: 12 h / -78 °C 3.3: 0.5 h 4.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / tetrahydrofuran / 24 h / Inert atmosphere; Reflux 5.1: potassium carbonate; copper / nitrobenzene / 16 h / Reflux; Inert atmosphere 6.1: tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate / toluene / 7 h / Inert atmosphere; Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In water; N,N-dimethyl-formamide at 80℃; for 5h; Inert atmosphere; | 4.1 1) Synthesis of Intermediate H 15 g (45.7 mmol) of 4-bromo-2-iodo-1-nitrobenzene, 8.8 g (68.6 mmol) of 3-thienylboronic acid, 2.6 g (2.3 mmol) of Pd(pph3)2, 12.6 g (91.4 mmol) of K2CO3, 300 ml of DMF and 80 ml of water and placed under nitrogen, followed by heating and stirring at 80[deg.] C. for 5 h. After the reaction was completed, the mixture was allowed to cool to room temperature. The solution was extracted with 100 ml of ethyl acetate (3 times) and 300 ml of water. Organic layer used anhydrousDry over magnesium sulfate and evaporate the solvent under reduced pressure. The residue was purified by silica gel column chromatography to give a yellow liquid(11.7 g, 41.2 mmol, yield: 90.1%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
20.2 g | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,4-dioxane; for 6h;Reflux; | 20.8 g of the <strong>[890042-13-4]2-triphenyleneboronic acid pinacol ester</strong> prepared in Example 1,22 g of 4-iodo-3-nitro-1-bromobenzene,65 g of potassium carbonate and 0.7 g of palladium tetrakistriphenylphosphine were dissolved in 290 ml of a 50% aqueous dioxane solution,After heating and refluxing reaction for about 6 hours, the disappearance of the raw material <strong>[890042-13-4]2-triphenyleneboronic acid pinacol ester</strong> was confirmed by TLC and then cooled to room temperature.The reaction mixture was filtered through diatomaceous earth to remove solid components. To the filtrate was added 200 ml of water, 300 ml of dichloromethane was added, and the mixture was stirred for 30 minutes and then layered. The separated organic layer was washed twice with 200 ml of water, layered, dehydrated with anhydrous magnesium sulfate, and short-columned with silica gel in an appropriate amount. After the filtrate is concentrated under reduced pressure, 120 ml of isopropanol is added to the solution, which is then heated to reflux for 1 hour and then cooled to room temperature to crystallize. The precipitate was filtered, washed with isopropanol and dried to obtain 20.2 g of 2- (5-bromo-2-nitrophenyl) triphenylene as an off-white powder in a purity of 96.98% by liquid chromatography. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane for 5h; Inert atmosphere; Reflux; | 16 Preparation 16: Synthesis of Compound 2-89 Synthesis of compound 2-89-1:32.8 g of dibenzofuran-2-boronic acid was dissolved in 400 ml of 1,4-dioxane solvent.Stirring under nitrogen, adding 21.2 g of dibenzofuran-2-boronic acid,39.8 g of K2CO3 and 1.6 g of tetrakis(triphenylphosphine)palladium were heated to reflux reaction.After 5 hours, the basic reaction of the raw materials was determined by HPLC, and the reaction solution was dried under reduced pressure.The residue was subjected to column chromatography to give 27.6 g of Compound 1-89-1 (yield 75%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With potassium phosphate; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane; water at 80℃; for 8h; Inert atmosphere; | 1.2 In a nitrogen atmosphere, Compound 14-1 (4-bromo-2-iodo-1-nitrobenzene) (231 g, 704 mmol), 1,4-dioxane (2.3 L), 2-chlorophenylboronic acid (132 g, 844 mmol), a 2 M K3PO4 aqueous solution (704 ml), and Pd(PPh3)4 (24.4 g, 21.1 mmol) were mixed and stirred at a temperature of 80° C. for 8 hours. The reaction solution was cooled to room temperature, and H2O was added thereto. The organic layer was extracted therefrom by using ethyl acetate, dried by using anhydrous magnesium sulfate, filtered, and then concentrated. The resultant obtained therefrom was purified by silica gel chromatography (hexane:CH2Cl2=10:1 as developing solvent) to provide Compound 14-2 that was a yellow solid. 210 g of Compound 14-2 was obtained, and the yield of Compound 14-2 was 95%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,2-dimethoxyethane; water at 20℃; for 12h; Inert atmosphere; Reflux; | 1.S1 Embodiment 1 S1, under nitrogen protection, add 42.5 g of 2-iodo-4-bromonitrobenzene and 22.4 g of biphenyl-2-boronic acid to a clean 1000 ml four-neck reaction flask.400ml DME and 200ml water, stir and dissolve, add 0.5g Pd(PPh3)4 at room temperature.Then add 32g of potassium carbonate; heat to reflux, stir for 12h, after the reaction is completed,The DME was recovered by distillation under reduced pressure, and after distillation, the product was extracted by adding 250 ml of dichloromethane.The lower organic layer is collected, and the organic layer is washed once with water.Dry over anhydrous sodium sulfate, filter, and recover the dichloromethane to give a yellow solid.After crystallization from ethanol, a yellow solid is obtained.Drying 35.2g, the yield was 83%; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: 4-bromo-2-iodo-1-nitrobenzene With phenylmagnesium chloride In tetrahydrofuran at -40℃; for 0.25h; Inert atmosphere; Stage #2: 1-methyl-1H-indole-2-carboxaldehyde In tetrahydrofuran at -40 - 20℃; for 0.5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: phenylmagnesium chloride / tetrahydrofuran / 0.25 h / -40 °C / Inert atmosphere 1.2: 0.5 h / -40 - 20 °C 2.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: phenylmagnesium chloride / tetrahydrofuran / 0.25 h / -40 °C / Inert atmosphere 1.2: 0.5 h / -40 - 20 °C 2.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 20 °C / Inert atmosphere 3.1: iron; hydrogenchloride / ethanol; water / 1 h / 100 °C / Schlenk technique 4.1: iron(III) trifluoromethanesulfonate; dipotassium peroxodisulfate / dimethyl sulfoxide / 2 h / 60 °C / Schlenk technique; Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: phenylmagnesium chloride / tetrahydrofuran / 0.25 h / -40 °C / Inert atmosphere 1.2: 0.5 h / -40 - 20 °C 2.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 20 °C / Inert atmosphere 3.1: iron; hydrogenchloride / ethanol; water / 1 h / 100 °C / Schlenk technique |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1.59 g | With potassium phosphate; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane; water at 100℃; for 17h; Sealed tube; | 26.4; 27.4 Step 4: 5'-bromo-4-chloro-2,3-dimethyl-2'-nitro-l,r-biphenyl To a solution of 4-bromo-2-iodo-l -nitrobenzene (753 mg, 2.30 mmol), 2-(4- chloro-2,3-dimethylphenyl)-4,4,5,5-tetramethyl-l,3,2-dioxaborolane (612 mg, 2.30 mmol), and Pd(Ph3P)4 (133 mg, 0.115 mmol) in 1,4-dioxane (15 mL) was added 2M aqueous potassium phosphate tribasic (3.44 mL, 6.88 mmol) and the biphasic mixture was degassed with nitrogen for 10 min. The vial was sealed and stirred at 100 °C for 17 h. Upon completion, the reaction mixture was cooled to room temperature. A duplicate reaction mixture of identical scale was run and then both reaction mixtures were combined. The material was concentrated and diluted with DCM and water. The organic layer was separated, and the aqueous layer was extracted twice with DCM. The combined organic layer was dried over sodium sulfate, filtered, and concentrated. The crude material was taken up in toluene and loaded onto silica gel for purification by silica gel column chromatography eluting with Hex/DCM 0-30% to obtain 1.59 g of 5'-bromo- 4-chloro-2,3-dimethyl-2'-nitro-l,r-biphenyl, contaminated with small amount byproducts. HPLC fe 1.22 min (analytical HPLC Method TS1). NMR (499 MHz, CHLOROFORM-d) d 7.89 (d, 7=8.8 Hz, 1H), 7.66 (dd, 7=8.8, 2.2 Hz, 1H), 7.46 (d, 7=2.1 Hz, 1H), 7.26 (d, 7=8.1 Hz, 1H), 6.87 (d, 7= 8.2 Hz, 1H), 2.39 (s, 3H), 2.05 (s, 3H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 80℃; for 12h; Inert atmosphere; | 1 1. Synthesis of Intermediate 2-1-1 Add Intermediate 2-1 (22.79 g, 61.4 mmol), 4-bromo-2-iodo-1-nitrobenzene (20.13 g, 61.4 mmol) into a 500 ml reaction flask,Tetrakis(triphenylphosphine)palladium (5% by mole), potassium carbonate (17.0 g, 122.8 mmol), 1,4-dioxane (200 mL) and water (50 mL). The reaction system was heated to 80 degrees Celsius 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 2-1-1 (20.38 g, yield 80%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water for 24h; Reflux; | 4 Synthesis Example 4: Preparation of intermediates Y2-11 and Y2-12 Dissolve cc-1 (36.22g, 100mmol) in 400mL of tetrahydrofuran solvent in a reaction flask, add dd-3 (49.18g, 150mmol), Pd(PPh3)4 (5.78g, 5.0mmol), K2CO3 (38.70g) , 280.0mmol) and 150mL of distilled water, the mixture was stirred, heated to reflux and reacted for 24h. After the reaction, the reaction mixture was diluted with water, extracted with dichloromethane, the organic phase was collected, dried with anhydrous MgSO4, filtered, and the filtrate was concentrated under reduced pressure to remove the solvent. The crude product was separated, purified and refined by column chromatography using chloroform/ethyl acetate (2:1) as the eluent to obtain intermediate A2-3 (35.25 g, yield 68%), and the solid purity determined by HPLC was ≧99.7%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | With tetrakis-(triphenylphosphine)-palladium; potassium carbonate In tetrahydrofuran; lithium hydroxide monohydrate for 24h; Reflux; | 1.2 Preparation of Intermediate D-69: In a reaction flask, the intermediate C-69 (29.91 g, 60 mmol) was dissolved in 400 mL of tetrahydrofuran, and the raw material c-69 (29.51 g, 90 mmol), Pd(PPh3)4 (3.47 g, 3.0 mmol), K2CO3 ( 23.22g, 168.0mmol) and 100mL distilled water,The mixture was stirred and heated to reflux for 24 h. After the reaction is over,The reaction mixture was diluted with water, extracted with dichloromethane, the organic phase was collected,Dry with anhydrous MgSO4, filter, and concentrate the filtrate under reduced pressure to remove the solvent. The crude product is separated and purified by column chromatography using chloroform/ethyl acetate (2:1) as the eluent.Intermediate D-69 (26.32 g, 67% yield) was obtained with HPLC purity > 99.51%. |
Tags: 343864-78-8 synthesis path| 343864-78-8 SDS| 343864-78-8 COA| 343864-78-8 purity| 343864-78-8 application| 343864-78-8 NMR| 343864-78-8 COA| 343864-78-8 structure
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P280 | Wear protective gloves/protective clothing/eye protection/face protection. |
P281 | Use personal protective equipment as required. |
P282 | Wear cold insulating gloves/face shield/eye protection. |
P283 | Wear fire/flame resistant/retardant clothing. |
P284 | Wear respiratory protection. |
P285 | In case of inadequate ventilation wear respiratory protection. |
P231 + P232 | Handle under inert gas. Protect from moisture. |
P235 + P410 | Keep cool. Protect from sunlight. |
Response | |
Code | Phrase |
P301 | IF SWALLOWED: |
P304 | IF INHALED: |
P305 | IF IN EYES: |
P306 | IF ON CLOTHING: |
P307 | IF exposed: |
P308 | IF exposed or concerned: |
P309 | IF exposed or if you feel unwell: |
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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