Alternatived Products of [ 1427213-44-2 ]
Product Details of [ 1427213-44-2 ]
| CAS No. : | 1427213-44-2 |
MDL No. : | MFCD32670107 |
| Formula : |
C30H28BNO2
|
Boiling Point : |
- |
| Linear Structure Formula : | - |
InChI Key : | WGAVHWLZSBXTLO-UHFFFAOYSA-N |
| M.W : |
445.36
|
Pubchem ID : | 71100139 |
| Synonyms : |
|
Safety of [ 1427213-44-2 ]
Application In Synthesis of [ 1427213-44-2 ]
* 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.
- Downstream synthetic route of [ 1427213-44-2 ]
| Yield | Reaction Conditions | Operation in experiment |
| 83% |
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In N,N-dimethyl-formamide at 90℃; |
4.4 Sub 1-IV-1 synthesis
General procedure: Said Sub 1-III-1 obtained in the synthesis (104.03g, 322.9mmol) senses a rotation velocity of the disk to a DMF to in round bottom flask , Bis (pinacolato) diboron (90.19g, 355.2mmol), Pd (dppf) Cl 2 (7.91g, 9.7mmol), KOAc (95.06g, 968.6mmol) added 90 °C stirring section. When reaction is completed by etching are removed and then the DMF via fractional distillation CH 2 Cl 2 extracted and water. Organic layer MgSO 4 to dry a silicagel column with a compound formed after the products and recrystallization 101.34g (yield: 85%)is obtained. |
| 70% |
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In N,N-dimethyl-formamide at 90℃; |
10.2 synthetic e.g. Sub 1-IV-1 intermediates
General procedure: Sub 1-III-1 (76.78g, 238.3mmol) senses a rotation velocity of the disk to a DMF to in round bottom flask , Bis (pinacolato) diboron (66.57g, 262.1mmol), Pd (dppf) Cl 2 (5.84g, 7.1mmol), KOAc (70.16g, 714.9mmol) added 90 °C stirring section. When reaction is completed by etching are removed and then the DMF via fractional distillation CH 2 Cl 2 extracted and water. Organic layer MgSO 4 to dry a silicagel column with a compound formed after the products and recrystallization 73.92g (yield: 84%)is obtained. |
| 70% |
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In N,N-dimethyl-formamide at 90℃; |
I.10.2 Intermediate Sub1-IV-1 Synthesis
General procedure: Sub 1-III-1 (76.78g, 238.3mmol) obtained in the above synthesis was dissolved inDMF in a round bottom flask, Bis (pinacolato) diboron (66.57g, 262.1mmol), Pd (dppf)Cl2 (5.84g, 7.1 mmol), was added KOAc (70.16g, 714.9mmol) and stirred at 90 ° C.When the reaction is complete, the DMF was removed by distillation and extracted withwater and CH2Cl2. The resulting compound and the organic layer was dried over MgSO4 and concentrated to silicagel column and the product was recrystallized 73.92g: (yield:84%). |
|
Stage #1: With n-butyllithium In tetrahydrofuran at -78℃; for 2h; Inert atmosphere;
Stage #2: In tetrahydrofuran at -78℃; for 2h; |
7; 17 Synthesis of Intermediate 16-a
General procedure: Synthesis of Intermediate 16-a 10 g of 2-bromo-9-phenyl-9H-carbazole was put in a reaction vessel, which was then supplied with N2 in a vacuum, followed by an addition of 69 ml of anhydrous THF to obtain a mixture. While the temperature of the mixture was maintained at about -78° C., 13.04 ml (1.05 eq) of n-BuLi was slowly dropwise added thereto. The resulting mixture was stirred for about 2 hours while being kept at the same temperature, followed by an addition of 7.6 ml (1.2 eq) of 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane and stirring for about 2 hours. The solvent was removed from the mixture using a rotary evaporator. The reaction product was extracted twice with 200 ml of dichloromethane (CH2Cl2) and then 150 ml of water 200 ml. The organic layer was collected and was dried using magnesium sulfate to evaporate the solvent. The residue was separated and purified by silica gel column chromatography to obtain 9 g of Intermediate 16-2 (Yield: 78%). This compound was identified using LC-MS. C24H24BNO2: M+ 369.19 |
- 2
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[ 1393835-87-4 ]
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[ 73183-34-3 ]
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9-([1,1'-biphenyl]-4-yl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
| 63% |
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In N,N-dimethyl-formamide; at 150℃; for 24h;Inert atmosphere; |
In the nitrogen environment, Intermediate H 25.5 g (64.15 mmol)Was dissolved in 260 ml of dimethylformamide (DMF)Bis (pinacolato) diboron 21.2 g (83.4 mmol),(1,1'-bis (diphenylphosphine) ferrocene) dichloropalladium (II)2.62 g (3.2 mmol) of potassium acetate and 9.5 g (96.23 mmol)And the mixture was refluxed by heating at 150 C for 24 hours.After completion of the reaction, water was added to the reaction solution, the mixture was filtered,And dried in a vacuum oven. The thus obtained residueThe separated and purified by column chromatography18 g (63%) of Intermediate I was obtained. |
- 3
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[ CAS Unavailable ]
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[ 1427213-44-2 ]
-
[ 1621608-76-1 ]
| Yield | Reaction Conditions | Operation in experiment |
| 39% |
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water; toluene Reflux; |
3.1 Step 1: Synthesis of intermediate product (C)
3-Bromoacridin-9 (10H) -one 5.00 g (18.24 mmol), 9 - ([1,1'-biphenyl] -4-yl) -2- (4,4,5,5-tetramethyl- 2.11 g (1.82 mmol) of tetrakistriphenylphosphine palladium (0) (Pd (PPh3) 4) and 7.56 g (1.82 mmol) of potassium carbonate were added to a solution of 9.75 g (21.89 mmol) 54.72 mmol) was added to a mixed solution of 30 mL of toluene, 30 mL of tetrahydrofuran and 30 mL of water, and the mixture was stirred under reflux. After completion of the reaction, the reaction mixture was cooled to room temperature, and the precipitate that had been dwelling in 1 L of methanol was extracted. The precipitate was dissolved in 3 L of 1,2-dichlorobenzene with 10 g of activated carbon, followed by vacuum filtration. The filtrate concentrated to 150 ml was precipitated in 1 L of methanol to obtain 3.61 g (yield 39%) of Intermediate (C) as a target compound. |
- 4
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[ CAS Unavailable ]
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[ 1427213-44-2 ]
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[ 1621608-77-2 ]
| Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / toluene; tetrahydrofuran; water / Reflux
2: bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate; tri-tert-butyl phosphine / 5,5-dimethyl-1,3-cyclohexadiene / Heating |
|
- 5
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[ 1427213-44-2 ]
-
[ 1445863-32-0 ]
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[ 1621608-91-0 ]
| Yield | Reaction Conditions | Operation in experiment |
| 49% |
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water; toluene Reflux; |
13.2 Step 2: Synthesis of Compound A-13
Intermediate (M) 5.77 g (11.73 mmol), 9 - ([1,1'-biphenyl] -4-yl) -2- (4,4,5,5-tetramethyl- 1,3,2-dioxaborolan-2-yl) -9H-carbazole 6.27 g (14.07 mmol), 1.35 g (1.17 mmol) of tetrakistriphenylphosphine palladium (0) (Pd (PPh3) 4) and 4.86 g (35.18 mmol) of potassium carbonate were dissolved in 20 mL of toluene and tetrahydrofuran, 20 mL, and water (20 mL), and the mixture was stirred under reflux. After completion of the reaction, the reaction mixture was poured into 1 L of methanol to obtain a precipitate. The precipitate was dissolved in 1 L of 1,2-dichlorobenzene by heating, and then filtered through silica gel to obtain 4.19 g (yield 49%) of the target compound A-13 |
- 6
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[ 1472062-94-4 ]
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[ 1427213-44-2 ]
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[ 2416120-01-7 ]
| Yield | Reaction Conditions | Operation in experiment |
| 84.9% |
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene Inert atmosphere; Reflux; |
1.3 Step 3: Synthesis of Compound 16
Intermediate C (4.6 g, 10.33 mmol), intermediate D (3.91 g, 11.36 mmol), Pd(PPh3)4 (0.60 g, 0.52 mmol), K2CO3 (2.86 g, 20.66 mmol) were added to toluene (48 mL), EtOH (12 mL), H2O (12 mL) in a three-necked round bottom flask, protected by nitrogen, and heated to reflux overnight. Heating was stopped and the reaction was cooled to room temperature. The reaction was suctioned under reduced pressure, and the solid was sequentially washed with water and methanol several times. The solid was recrystallized from toluene to obtain Compound 16 (5.5 g, 8.78 mmol) as a white solid in a yield of 84.9%. The product was identified as the target product with a molecular weight of 627 |
- 7
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[ 3652-90-2 ]
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[ 1427213-44-2 ]
| Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1: copper(l) chloride; 18-crown-6 ether; 1,10-Phenanthroline; potassium carbonate / 1-methyl-pyrrolidin-2-one / 180 °C / Inert atmosphere
2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,4-dioxane / Inert atmosphere; Reflux |
|
- 8
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[ 1591-31-7 ]
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[ 1427213-44-2 ]
| Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1: copper(l) chloride; 18-crown-6 ether; 1,10-Phenanthroline; potassium carbonate / 1-methyl-pyrrolidin-2-one / 180 °C / Inert atmosphere
2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,4-dioxane / Inert atmosphere; Reflux |
|
- 9
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[ 1427213-44-2 ]
-
[ CAS Unavailable ]
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[ 2821862-17-1 ]
| Yield | Reaction Conditions | Operation in experiment |
| 82.96% |
With tetrakis-(triphenylphosphine)-palladium; potassium carbonate In ethanol; lithium hydroxide monohydrate; toluene at 90℃; for 24h; Inert atmosphere; |
3.2
(2) Under nitrogen protection system, weigh compound S002 (44.91mmol, 20g), S003 (49.4mmol, 19.18g), anhydrous potassium carbonate (89.81mmol, 12.41g) into the reaction system, then put into the reaction system Add 150ml toluene solution, 150ml ethanol, 75ml pure water, then add tetrakis (triphenylphosphine) palladium (1.35mmol, 1.56g), heat 90 , stir and react for 24 hours, after the reaction stops, the system is cooled to room temperature, Precipitation was precipitated, and the precipitate was filtered with suction, rinsed and dried with absolute ethanol to obtain a solid powder, and a mixed solution of dichloromethane and petroleum ether was used as a developing solvent, and silica gel column chromatography was used. The filtrate was concentrated and the solid was separated to obtain F019 (23.35 g , yield: 82.96%).HPLC purity: greater than 99.9%; |
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