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Chemical Structure| 1262866-93-2
Chemical Structure| 1262866-93-2
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Product Details of [ 1262866-93-2 ]

CAS No. :1262866-93-2 MDL No. :MFCD28967157
Formula : C20H13ClN2 Boiling Point : -
Linear Structure Formula :- InChI Key :VSMPNDGQPFFGPG-UHFFFAOYSA-N
M.W : 316.78 Pubchem ID :87160724
Synonyms :

Safety of [ 1262866-93-2 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501 UN#:
Hazard Statements:H302-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 1262866-93-2 ]

* 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 [ 1262866-93-2 ]

[ 1262866-93-2 ] Synthesis Path-Downstream   1~73

  • 1
  • [ 607-68-1 ]
  • [ 5122-94-1 ]
  • [ 1262866-93-2 ]
YieldReaction ConditionsOperation in experiment
80% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; for 5h;Inert atmosphere; Heating; In a three-necked flask, 2,4-dichloroquinazoline (6 g, 30 mmol), <strong>[5122-94-1]biphenylboronic acid</strong> (6 g, 30 mmol), potassium carbonate(8.3 g, 60 mmol), tetrakistriphenylphosphine palladium (0.3 g), tetrahydrofuran (60 ml) and water (20 ml)The mixture was heated under nitrogen for 5 hours, cooled and filtered. The crude product was recrystallized from tetrahydrofuran and ethanol to give 7.6 g of product in 80% yield.
78% With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; water; toluene; at 120℃; for 15h; 2,4-dichloroquinazoline (5g, 25.1mmol), biphenyl-4-ylboronic acid (5.4g, 27.3mmol), Na2CO3 (8g, 75.3mmol) and Pd(PPh3)4 (1.45g, 1.26mmol) were put in a mixed solution of toluene (120mL)/ EtOH (30mL)/ purified water (30mL), followed by stirring at 120C for 15 hours. After the reaction was completed, the resultant material was cooled to room temperature, and then stood. Then, the water layer was removed and the organic layer was concentrated, followed by silica column purification, thereby obtaining Compound 12-1 (6.2 g, 78%).
70% With tetrakis(triphenylphosphine) palladium(0); tetrabutylammomium bromide; sodium carbonate; In 1,4-dioxane; water; at 80℃; for 6h;Inert atmosphere; Under the environment of nitrogen, will (19.9 g, 100 mmol) compound 1 - 23 - 1, (19.8 g, 100 mmol) compound 1 - 17 - 1, (5.8 g, 5 mmol) Pd (PPh3)4, (6.4 G, 20.0 mmol) sodium carbonate, (1.8 g, 5 . 64 mmol) [...] ammonium bromide, 250mL1, 4 - dioxane and 50 ml water is added to a 500 ml three-opening in the bottle, heating 80 C reaction 6 hours, to the completion of the reaction, the reaction liquid inverted in 500 ml of pure water, the separated solid filtered, the filter residue recrystallization purification, to obtain intermediate 1 - 23 - 2, yield 70%.
64% With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; water; toluene; at 120℃; for 5h; Preparation of Compound 2-1 [150] 2,4-dichloroquinazoline (8.1g, 40.6mmol), biphenyl phenylboronic acid (8.0g, 40.6mmol), toluene 200mL, ethanol 50mL and water 50mL were mixed and Pd(PPh3)4 (1.9g, 1.64mmol) and K2CO3 (12.9g, 122mmol) were added. The mixture was stirred at 120C for 5 hours and cooled to room temperature, and the reaction was terminated with aqueous ammonium chloride 200mL. The mixture was extracted with EA 500mL, and washed with distilled water 50mL. The obtained organic layer was dried with anhydrous MgSO4, and the organic solvent was removed under reduced pressure. Subsequently, silica gel filtration and then recrystallization were performed, yielding Compound 2-1 (8.2g, 25.9mmol, 64%).
51.4% With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In water; toluene; at 90℃; for 2h; Preparation of compound C-1-2 [98] After dissolving 2,4-dichloroquinazoline (30g, 151mmol), biphenyl boronic acid (9.2g, 75.3mmol), Pd(PPh3)4 (2.6g, 2.3mmol) and Na2CO3 (16g, 150mmol) in a mixture of toluene (300mL) and distilled water (75mL), the reaction mixture was stirred for 2 hours at 90C. The resulting organic layer was distillated under reduced pressure, and then was triturated with MeOH. The obtained solid was dissolved in MC, was filtered through silica, and then was triturated with MC and hexane to produce compound C-1-2 (9.3g, 51.4%).
50.26% With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; toluene; at 100℃; for 3h; After 2,4-Dichloroquinazol in (15 g, 75.36 mmol), <strong>[5122-94-1]4-<strong>[5122-94-1]biphenylboronic acid</strong></strong> (16.4 g, 82.89 mmol), Pd(PPh3)4 (3.76 mmol), 2M-Na2CO3 (110 mL) and ethanol (50 mL) were dissolved in toluene (30OmL), the mixture was stirred under reflux at 100 C for 3 hours. Upon completion of the reaction, the mixture was cooled at room temperature. After extracting with ethyl acetate and washing with distilled water, remaining moisture was removed by using magnesium sulfate. Drying followed by column separation yielded Compound F-I (12 g, 37.88 mmol, 50.26 %) .
50% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; at 80℃; for 12h;Inert atmosphere; Intermediate 1-5 (79.5 g, 50%) was obtained according to the same method as Synthesis Example 3 except for using 2,4-dichloroquinazoline (100 g, 502 mmol) purchased from P&H Tech Co., Ltd. (http://www.phtech.co.hi) and biphenyl-4-boronic acid (89.5 g, 452 mmol). j0148] HRMS (70 eV, EI+): mlz calcd for C2OH13C1N2:316.0767, found: 316.j0149] Elemental Analysis: C, 76%; H, 4%
47% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In ethanol; water; toluene; at 70 - 80℃; for 3h; 2,4-dichloroquinazoline (20 g, 0.1 mol), biphenyl-4-yl boronic acid (18.9 g, 0.1 mol), Pd(PPh3)4 (3.5 g, 3.01 mmol) and Na2CO3 (31.9 g, 0.3 mol) were added to toluene 800 mL, EtOH 200 mL and purified water 200 mL. After stirring the reaction mixture for 3 hours at 70 to 80C, an aqueous layer was removed from the mixture by a gravity separation. The obtained organic layer was concentrated, and then was purified by silica column chromatography to obtain compound C-2-2 (15 g, 47%).

  • 2
  • [ 1262866-93-2 ]
  • [ 1262866-95-4 ]
  • [ 1262866-96-5 ]
YieldReaction ConditionsOperation in experiment
57.68% Stage #1: 2-(triphenylsilyl)-9H-carbazole With sodium hydride In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: 4-([1,1′-biphenyl]-4-yl)-2-chloroquinazoline In N,N-dimethyl-formamide at 20℃; for 12h; 6 After Compound F-5 (4.8 g, 11.36 mmol) was dissolved in dimethyl formamide (100 mL) , the mixture was added into solution, in which NaH (0.56 g, 14.20 mmol) was dissolved in DMF (25 mL). the resultant mixture was stirred at room temperature for 1 hour. Subsequently, solution, in which Compound F-I (3 g, 9.47 mmol) was dissolved in dimethylformamide (50 mL), was added thereto and the mixture was stirred at room temperature for 12 hours. After washing with distilled water and extracting with ethyl acetate, distillation under reduced pressure was performed. After the product was dissolved in chloroform and silica filtering was performed. Compound 150 (2.8 g, 5.46 mmol, 57.68 %) was obtained by recrystallization with methanol, ethyl acetate and dimethylformamide.
  • 3
  • [ 1262866-93-2 ]
  • [ 1262866-99-8 ]
  • [ 1262867-00-4 ]
YieldReaction ConditionsOperation in experiment
44.37% Stage #1: C25H21NSi With sodium hydride In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: 4-([1,1′-biphenyl]-4-yl)-2-chloroquinazoline In N,N-dimethyl-formamide at 20℃; for 12h; 7 After Compound G-4 (5.04 g, 13.88 mmol) was dissolved in dimethyl formamide (30 mL), the mixture was added into solution, in which NaH (0.75 g, 18.95 mmol) was dissolved in DMF (30 mL). The resultant mixture was stirred at room temperature for 1 hour. After solution, in which Compound F- 1 (4 g, 12.62 mmol) was dissolved in dimethylformamide (140 mL), was added thereto, the mixture was stirred at room temperature for 12 hours. After washing with distilled water and extracting with ethyl acetate, distillation under reduced pressure were performed. After dissolving the product in chloroform and performing silica filtering, Compound 154 (3.6 g, 5.59 mmol, 44.37 %) was obtained by recrystallization with methanol, ethyl acetate and dimethyl formamide.
  • 4
  • [ 1262866-93-2 ]
  • [ 1346669-46-2 ]
  • [ 1365549-07-0 ]
YieldReaction ConditionsOperation in experiment
18% With sodium hydride In N,N-dimethyl-formamide at 20℃; for 5h; 9 Preparation of Compound 128 [215] Compound 2-1 (3g, 8.99mmol) and Compound 9-1 (3.14g, 9.89mmol) were suspended in anhydrous DMF 50mL, and 60% NaH (0.54g, 13.5mmol) was added at room temperature. The mixture was stirred at room temperature for 5 hours. After termination of the reaction, MeOH 3mL was added in droplets and the solid was obtained due to excessive MeOH, and silica column purification, suspending with EA, filtration and then crystallization with THF were performed, yielding Compound 128 (1g, 18%).[216] MS/FAB found 613.70, calculated 613.22
  • 5
  • [ 1262866-93-2 ]
  • [ 1365549-03-6 ]
  • [ 1365549-05-8 ]
YieldReaction ConditionsOperation in experiment
46% With sodium hydride In N,N-dimethyl-formamide at 20℃; for 12h; 8 Preparation of Compound 116 [208] Compound 8-1 (3g, 7.8mmol) and Compound 2-1 (2.1g, 7.8mmol) were suspended in DMF 30mL, and 60% NaH (376mg, 9.4 mmol) was added at room temperature, and the mixture was stirred for 12 hours. Purified water 500mL was added and the mixture was filtered under reduced pressure. The obtained solid was triturated with MeOH/EA, DMF and then EA/THF in that order. The resultant product was dissolved in MC, silica filtered, and triturated with MeOH/EA, yielding Compound 116 (2.4g, 46%).[209] MS/FAB found 663.76, calculated 663.23
  • 6
  • [ 1262866-93-2 ]
  • [ 1260228-95-2 ]
  • [ 1373227-59-8 ]
YieldReaction ConditionsOperation in experiment
65% After Compound 14-2 (5.75g, 20.3mmol) was dissolved in DMF (50mL), NaH (1g, 27.6mmol) was slowly added and stirred for 40 minutes. After stirring, 4-(biphenyl-4-yl)-2-chloroquinazoline (5.84g, 18.4mmol) was slowly added to the mixture and stirred at room temperature for 24 hours. Upon completion of the reaction, distilled water (300mL) was slowly added to the reaction mixture and stirred for 30 minutes to produce a solid product. Column separation was conducted on the solid product, yielding Compound 4 (6.5g, 65%). MS/EIMS: 563.69(found), 563.24(calculated)
  • 7
  • [ 1262866-93-2 ]
  • [ 1257220-47-5 ]
  • [ 1373227-56-5 ]
YieldReaction ConditionsOperation in experiment
70% Compound 12-2 (5g, 17.64mmol) and DMF (100mL) were mixed, and NaH (1.1g, 26.46mmol, 60% dispersion in mineral oil) was slowly added to the mixture. The mixture was stirred at room temperature for 30 minutes. After stirring, 4-(biphenyl-4-yl)-2-chloroquinazoline(5.6g, 17.64mmol) was slowly added to the mixture and stirred for 4 hours. After stirring, a solid product was obtained by adding distilled water (300mL) to the reaction mixture and stirring the reaction mixture for 30 minutes. Column separation was conducted on the solid product, yielding Compound 3 (6.9g, 70%). MS/EIMS: 563.69(found), 563.24(calculated)
  • 8
  • [ 1262866-93-2 ]
  • [ 1373227-16-7 ]
  • [ 1373227-19-0 ]
YieldReaction ConditionsOperation in experiment
60.4% With sodium carbonate In ethanol; water; toluene at 120℃; for 24h; Compound 1-5 (5g, 12.4mmol), 4-(biphenyl-4-yl)-2-chloroquinazoline (2.62g, 8.3mmol), Pd(PPh3)4 (600mg, 0.52mmol), and Na2CO3 (2.63g, 24.8mmol) were dissolved in a mixture comprising toluene (300mL), EtOH (100mL) and distilled water (100mL) and stirred at 120°C for one day. The mixture was cooled to room temperature, extracted with EA and distilled water, dissolved in chloroform to perform silica filtration, and recrystallized from MC and hexane. Further, two recrysallizations from DMF were carried out, followed by performing trituration with MeOH/EA, yielding Compound 1 (3.2g, 60.4%).[78] MS/EIMS: 639.79(exp.), 639.27(calculated)
  • 9
  • [ 1262866-93-2 ]
  • [ 1391729-63-7 ]
  • [ 1373227-25-8 ]
YieldReaction ConditionsOperation in experiment
28% With potassium carbonate In toluene at 100℃; for 12h; 4-(biphenyl-4-yl)-2-chloroquinazoline (2.1g, 6.56mol), Compound 2-4 (3.1g, 7.88mmol), Pd(PPh3)4 (379.5mg, 0.3285mmol), 2M K2CO3 (16mL) and toluene were added. The mixture was stirred for 12 hours at 100°C, and cooled to room temperature. The distilled water was added and the mixture was extracted with EA. Column separation was conducted, yielding Compound 49 (1.15g, 28%yield). MS/EIMS: 629.77(found), 629.19(calculated)
  • 10
  • [ 1262866-93-2 ]
  • [ 1357066-50-2 ]
  • [ 1373227-80-5 ]
YieldReaction ConditionsOperation in experiment
12% With sodium carbonate In ethanol; water; toluene at 120℃; for 5h; 25 Compound 25-2 (6.8g, 16.86mmol), 4-(biphenyl-4-yl)-2-chloroquinazoline (4g, 12.97mmol), Pd(PPh3)4 (0.8g, 0.65mmol), Na2CO3 (4.2g, 38.91mmol), toluene (70mL), ethanol (20mL) and distilled water (20mL) were mixed and stirred at 120? for 5 hours. The mixture was cooled to room temperature and distilled water was added. The mixture was extracted with EA. Column separation was conducted, yielding Compound 19 (1.0g, 12%). MS/EIMS: 639.79(found), 639.27(calculated)
  • 11
  • [ 1262866-93-2 ]
  • [ 1377576-73-2 ]
  • [ 1377576-77-6 ]
YieldReaction ConditionsOperation in experiment
47% With sodium hydride In N,N-dimethyl-formamide at 20℃; for 12h; 12 Compound 11-4 (2.3g, 4.6 mmol) and Compound 12-1 (1.75 g, 5.5 mmol) were suspended in DMF (33 mL), and then 60% NaH (221 mg, 5.5mmol) was put thereinto at room temperature, followed by stirring for 12 hours. After the stirring was completed, purified water (500 mL) was put thereinto, followed by filtering under reduced pressure. The thus obtained solid was subjected to sequential trituration with MeOH/EA, DMF, and EA/THF, and then dissolved in MC, followed by silica filtering and then trituration with MeOH/EA, thereby obtaining Compound 70 (1.7 g, 47%).[263] MS/EIMS found 778.90, calculated 778.27
  • 12
  • [ 1060735-14-9 ]
  • [ 1262866-93-2 ]
  • [ 1398393-76-4 ]
YieldReaction ConditionsOperation in experiment
47.4% With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 12h; After suspending compound C-2-2 (4.6 g, 14.7 mmol) and compound C-2-1 (5 g, 12.2 mmol) in DMF 80 mL, 60% NaH (881 g, 22 mmol) was added to the mixture at room temperature. The obtained reaction mixture was stirred for 12 hours. After adding purified water (1 L), the mixture was filtered under reduced pressure. The obtained solid was triturated with MeOH/EA, was dissolved in MC, was filtered through silica, and then was triturated with MC/n-hexane to obtain compound C-9 (4 g, 47.4%).
  • 13
  • [ 1262866-93-2 ]
  • [ 1204577-07-0 ]
  • [ 1398393-70-8 ]
YieldReaction ConditionsOperation in experiment
52% With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 12h; After suspending compound C-3-1 (5.5 g, 15.8 mmol) and compound C-2-2 (5 g, 15.8 mmol) in DMF 80 mL, 60% NaH (948 mg, 22 mmol) was added to the mixture at room temperature. The obtained reaction mixture was stirred for 12 hours. After adding purified water (1 L), the mixture was filtered under reduced pressure. The obtained solid was triturated with MeOH/EA, was dissolved in MC, was filtered through silica, and then was triturated with MC/n-hexane. Compound C-12 (5.2 g, 52%) was obtained.
  • 14
  • [ 1262866-93-2 ]
  • [ 1345202-03-0 ]
  • [ 1401939-41-0 ]
YieldReaction ConditionsOperation in experiment
51.5% With sodium hydride; In N,N-dimethyl-formamide; at 20℃; for 12h; Preparation of compound C-14 [100] After suspending compound C-1-1 (5.3 g, 14.7 mmol) and compound C-1-2 (5 g, 15.8 mmol) in DMF 80mL, 60% NaH (948 mg, 22 mmol) was added to the mixture at room temperature. The obtained reaction mixture was stirred for 12 hours. After adding purified water (1L), the mixture was filtered under reduced pressure. The obtained solid was triturated with MeOH/ethyl acetate, was dissolved in MC, was filtered through silica, and then was triturated with MC/n-hexane to obtain compound C-14 (5 g, 51.5%). [101] MS/FAB found 689; calculated 688.82
  • 15
  • [ 1262866-93-2 ]
  • [ 194-59-2 ]
  • C40H25N3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
46.9% With dmap; potassium carbonate; In N,N-dimethyl-formamide; for 2h;Reflux; Example 5: Preparation of compound A-1 Preparation of compound A-148 After introducing <strong>[194-59-2]7H-dibenzo[c,g]carbazole</strong> (5.00 g, 18.70 mmol), 4-([1,1'-biphenyl]-4-yl)-2-chloroquinazoline (7.11 g, 22.45 mmol), K2CO3(2.58 g, 18.70 mmol), and DMAP (1.14 g, 9.35 mmol) in DMF 100 mL, the mixture was stirred under reflux for 2 hours. The mixture was then cooled to room temperature, reversely added dropwise to MeOH 400 mL, and filtered under reduced pressure to obtain an ocherous solid. The solid was was dissolved in CHCl3140 mL under heat and filtered with silica. The filtrate was distilled under reduced pressure, solidified by adding methanol, and filtered under reduced pressure to obtain a lemon-colored solid. The solid was recrystallized with DMF to obtain compound A-1 (4.8 g, 46.9%).
  • 16
  • 2-chloro-4-iodoquinazoline [ No CAS ]
  • [ 5122-94-1 ]
  • [ 1262866-93-2 ]
YieldReaction ConditionsOperation in experiment
73% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In water; toluene for 24h; Inert atmosphere; Reflux; 10 Synthesis of Compound 10 0.10 mol of 2-chloro-4-iodoquinazoline and 0.12 mol of 4-biphenylyl boric acid were dissolved in 1 L of toluene. 0.15 mol of tetrakis(triphenylphosphine)palladium, 0.25 mol of potassium carbonate and 100 mL of distilled water were added under the protection of nitrogen gas. The reaction was carried out under stirring and reflux for 24 hours. After the reaction was ended, distilled water was added at normal temperature. The organic layer was collected by extraction with ethyl acetate, and then dried with anhydrous magnesium sulfate, followed by filtration. A liquid was obtained after distillation under reduced pressure, and then subjected to column chromatography. 0.073 mol of a white solid intermediate 4-([1,1′-biphenyl]-4-yl)-2-chloroquinazoline was obtained, with a yield of 73%.
  • 17
  • [ 1262866-93-2 ]
  • 13,13-dimethyl-7,13-dihydro-5H-indoloacridine [ No CAS ]
  • C61H42N6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
82% With triethylamine In tetrahydrofuran at 50 - 70℃; Inert atmosphere; 10 Synthesis of Compound 10 In nitrogen gas, 0.048 mol of the intermediate 4-([1,1′-biphenyl]-4-yl)-2-chloroquinazoline, 0.0576 mol of 13,13-dimethyl-7,13-dihydro-5H-indoloacridine, 0.0576 mol triethylamine, and tetrahydrofuran as a solvent were heated to 50° C.-70° C. After the reaction was ended, methanol was added at normal temperature, and then the produced solid was filtered off. The solid filtered off was added into and washed with distilled water and methanol. Then recrystallization was performed with dichloromethane and methanol, so as to obtain 0.0394 mol of compound 10, with a yield of 82%.
  • 18
  • [ 1262866-93-2 ]
  • 2-(6-([1,1′-biphenyl]-4-yl)dibenzo[b,d]thiophen-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane [ No CAS ]
  • C44H28N2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
79% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,2-dimethoxyethane; water Inert atmosphere; Reflux; Synthesis of Compound C65 A solution of 4-([1,1′-biphenyl]-4-yl)-2-chloroquinazoline (2.80 g, 8.85 mmol), 2-(6-([1,1′-biphenyl]-4-yl)dibenzo[b,d]thiophen-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (4.5 g, 9.73 mmol), Pd(PPh3)4 (0.204 g, 0.177 mmol), and K2CO3 (3.67 g, 26.5 mmol) in DME (80 ml) and water (15 ml) was refluxed under nitrogen overnight. After cooling to room temperature, the solid was collected by filtration, dissolved in boiling xylene (4 L) and filtered through a short plug of silica gel. Upon evaporation of the solvent, the crude product recrystallizes from xylene, and was triturated with ethyl acetate to yield Compound C65 (4.3 g, 6.97 mmol, 79% yield) as a white solid.
YieldReaction ConditionsOperation in experiment
75.1% With trichlorophosphate for 5h; Reflux; 17.2 A compound represented by [Formula 1-c] was synthesized by the following [Scheme 3]. General procedure: 50.0 g (225 mmol) of a compound represented by [Chemical Formula 1-b] obtained from [Scheme 2],Put in 500 mL of phosphorus oxychloride and stirred under reflux for 5 hours.When the reaction is complete, it is slowly added dropwise to the cooled water.When the dropwise addition was completed, the mixture was filtered, extracted with methylene chloride and water, and the organic layer was concentrated under reduced pressure and separated by column chromatography to obtain 41 g of a compound represented by [Formula 1-c]. (Yield 75.1%)
73.2% Stage #1: With potassium carbonate In ethanol; water; toluene for 0.5h; Heating; Stage #2: With tetrakis(triphenylphosphine) palladium(0) In ethanol; water; toluene for 2h; Synthesis of Intermediate 1-C-1 General procedure: Phenylboronic acid (PBA, CAS 98-80-6, 6.10 g, 50 mmol) and 2,4-dichloroquinazoline (CAS 607-68-1, And potassium carbonate (CAS 584-08-7, 41 g, 300 mmol) were dissolved in water, and the mixture was heated and stirred for 30 minutes. After 30 minutes, tetrakis (triphenylphosphine) palladium (0) (CAS 14221-01-3, 1.7 g, 1.5 mmol) was added and the mixture was further reacted for 2 hours. After completion of the reaction, an excess amount of water was added, and the mixture was extracted with ethyl acetate (ethyl acetate, ethyl acetate, EA (hereinafter)) to obtain an organic layer. Column purification was conducted to obtain 8.3 g of intermediate 1-C-1 (yield 68.7%).
61% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water at 70℃; Synthesis Example of Sub 2-2 General procedure: A starting material, 2,4-dichloroquinazoline (89.57 g, 450 mmol) was dissolved in THF in a round bottom flask, and then phenylboronic acid (65.84 g, 540 mmol), Pd(PPh3)4(26 g, 22.5 mmol), K2CO3(186.59 g, 1350 mmol)rand water were added, followed by stirring at 70° C. Upon completion of the reaction, the reaction product was extracted with CH2Cl2and water. The organic layer was dried over MgSO4and concentrated, and then the thus generated compound was subjected to a silica gel column and recrystallization to give a product 71.49 g (yield: 66%).
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water at 80℃; I Sub 1-32 Synthesis General procedure: in the above synthesised Sub 1-II-3 (17.43g, 63.4mmol) was dissolved in THF in a round bottom flask, 4,4,5,5-tetramethyl-2-phenyl-1,3,2-dioxaborolane (14.22 g, 69.7mmol), Pd (PPh3) 4 (2.93g, 2.5mmol), K2CO3 (26.27g, 190.1mmol), water was added and the resulting mixture was stirred at 80 C . After the reaction was completed, the organic layer was dried and extracted with water and CH2Cl2 over MgSO4, and concentrated to a silicagel column, and the resulting compound was recrystallized product 12.24g (yield: 61%) was obtained.

  • 20
  • [ 1262866-93-2 ]
  • 18H-benzo[5,10]benzofuro[3',2': 6,7]anthra[9,1-bc]carbazole [ No CAS ]
  • C52H29N3O [ No CAS ]
YieldReaction ConditionsOperation in experiment
61% With tris-(dibenzylideneacetone)dipalladium(0); triphenylphosphine; sodium t-butanolate In toluene at 100℃; for 24h; <Systhesis of 4-4> [0146] 18H-benzo [5,10] benzofuro [3 ', 2': 6,7] anthra [9, 1-bc] carbazole (8.6g, 20mmol) 4 - ([1,1'-biphenyl] -4-yl) -2-chloroquinazoline (7.6g, 24mmol) was placed in a toluene, Pd2 (dba) 3 ( 1.0g, 1mmol), PPh3 (0.5g, 2mmol), After NaOt-Bu (5.8g, 60mmol) was added, respectively, It is stirred for 24 hours under reflux at 100 . After extraction with ether and water, MgSO organic layer 4 dried, After concentration, to give the final Product (61% yield) of 8.7g product organics Silicagel column and recrystallized
  • 21
  • [ 1262866-93-2 ]
  • C48H29N3S3 [ No CAS ]
  • C68H41N5S3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
38% With tri-tert-butyl phosphine; palladium diacetate; sodium t-butanolate In toluene at 110℃; for 12h; 57 Synthesis Example 57: Synthesis of Inv 588 Under a stream of nitrogen IC-16 (5 g, 9.93 mmol) and 4-(diphenylamino)phenylboronic acid (3.45 g, 11.92 mmol), K2CO3 (4.12 g, 29.79 mmol) and THF/H2O (100ml/50ml) a mixed next, insert the Pd (PPh3) 4 (0.57 g, 5 mol%) at 40 °C was stirred at 80 °C for 12 hours. After completion of the reaction and extracted with methylene chloride, filtered, put MgSO4. Obtained after removal of the solvent from the organic layer was purified by column chromatography (Hexane: MC = 1: 1 (v / v)) was purified by scored intermediate compound (4.78g, yield 72%), the resulting intermediate compound (4.78 g, 7.16 mmol ) it is iodobenzene (2.19 g, 10.74 mmol), Cupowder (0.05 g, 0.72 mmol), K2CO3 (0.99 g, 7.16 mmol), Na2SO4 (1.02 g, 7.16 mmol), nitrobenzene (100ml) and the mixture and 200°C at 24 hours It was stirred. After completion of the reaction remove the nitrobenzene and methylene chlorideThe organic layer was separated, the water was removed using MgSO4. After removing the solvent in water is removed, the organic layer was purified by column chromatography (Hexane: MC = 2: 1 (v / v)) to obtain the intermediate compound (2.18 g, yield 41%) as a. The obtained intermediate compound (2.18 g, 2.93 mmol) is 4 - (biphenyl-4-yl)-2-chloroquinazoline (1.11 g, 3.52 mmol), Pd (OAc) 2 (0.03 g, 5mol%), NaO (t-bu ) (0.84 g, 8.79 mmol), P (t-bu) 3 (0.06 g, 0.29 mmol) and Toluene (100 ml) and mixed with 110 12 hours dongan stirring. After the reaction was terminated with ethyl acetate and then extracted with water to remove MgSO4 and purified by column chromatography (Hexane: EA = 2:1 (v / v)) to obtain the Inv 588 (1.14 g, yield 38%) was obtained
  • 22
  • [ 1262866-93-2 ]
  • C41H24ClN [ No CAS ]
  • C61H37N3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
77% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water for 3h; Reflux; Inert atmosphere; Example 16 Compound in 500ml round bottom flask in a nitrogen atmosphere E (4.37g, 13.84mmol), 4 - ([1,1'- biphenyl ] -4-yl ) -2-chloroAfter quinazoline ( 10.00g , 15.22mmol ) completely dissolved in 240ml of tetrahydrofuran was added a 2M aqueous potassium carbonate solution and 120mlAnd , tetrakis- , insert (triphenylphosphine) palladium ( 0.48g , 0.42mmol ) was stirred with heating for 3 hours. Room temperatureLowering the temperature to remove the water layer and dried over anhydrous magnesium sulfate and concentrated under reduced pressure and recrystallized with ethyl acetate 220mlPrescribed above compound 16: it was prepared ( 9.92g , yield 86%)
  • 23
  • [ 1262866-93-2 ]
  • C29H17N3 [ No CAS ]
  • C49H29N5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
93% With bis(tri-t-butylphosphine)palladium(0); sodium t-butanolate In 5,5-dimethyl-1,3-cyclohexadiene for 4h; Inert atmosphere; 9 Synthesis of Compound 1-9 Compound corresponding to the formula 3 (15.0g, 0.52mol) in a nitrogen atmosphere, 4 - ([1,1'-biphenyl] -4-yl) -2-chloro-quinazoline (18.93g, 0.57mol), the xylene (Xylene) was completely dissolved in 240ml, sodium -tert- butoxide (4.25g, 0.44mol) was added and bis (tri -tert- butylphosphine) palladium after loading (0.11g, 0.0018mol) for 4 h heated and stirred. And then it was cooled down to to room temperature to remove salts and concentrated under reduced pressure and recrystallized with ethyl acetate, the compound 1-9: a (19.84g, yield 93%) was prepared
  • 24
  • [ 1262866-93-2 ]
  • C36H24N2 [ No CAS ]
  • C56H36N4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
57% With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In toluene at 20℃; for 6h; Inert atmosphere; 47 Synthesis of compound 265 PBC-8 obtained in Preparation Example 5, under the flow of nitrogen (5.38 g, 10.00 mmol), 4-bromo-N,N-diphenyl-aniline (3.90 g, 12.00 mmol), Pd2(dba)3 (0.45 g, 0.50 mmol ), tri-tert-butylphosphine (0.1 g, 0.5 mmol) and sodium tert-butoxide (1.44 g, 15.00 mmol) and toluene (50 ml) and the mixture was stirred for 6 hours at room temperature. After the reaction terminated, the reaction mixture into a solid compound humul filter, and purified by column chromatography to obtain the objective compound of Compound 265 (4.14 g, yield 57%). 4-Bromo-N,N-diphenyl-aniline instead of 4-([1,1'-biphenyl]-4-yl)-2-chloro-quinazoline (3.80 g, 12.00 mmol) except for the use, and is synthesis example 44 was obtained the object compound of compound 278 (4.35 g, yield 57%) by following the same procedure.
  • 25
  • [ 1262866-93-2 ]
  • C24H16N2 [ No CAS ]
  • C44H28N4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
63% With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In toluene at 20℃; for 6h; Inert atmosphere; 11 Synthesis of compound 120 General procedure: A stream of nitrogen under the Preparation Example 1 obtained PBC-2 (3.30 g, 10.00 mmol), 4-bromo-N,N-diphenyl-aniline (3.90 g, 12.00 mmol), Pd2 (dba) 3 (0.45 g, 0.50 mmol ), tri-tert-butylphosphine (0.1 g, 0.5 mmol) sodium tert-butoxide(1.44 g, 15.00 mmol) and toluene (50 ml) the mixture was stirred 6 hours at room temperatureand. After the reaction was filtered, the solid compound into the terminated humul and purified by column chromatography to obtain the objective compound of Compound 113 (4.03 g, yield 70%).
  • 26
  • [ 1262866-93-2 ]
  • 13H-fluorenone[1,9-ab]carbazole [ No CAS ]
  • C42H25N3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
93% With bis(tri-t-butylphosphine)palladium(0); sodium t-butanolate In 5,5-dimethyl-1,3-cyclohexadiene for 2h; Inert atmosphere; Reflux; 9 Preparation of Compound 1-9 The compounds in the atmosphere of nitrogen 13H-fluorenone[1,9-ab]carbazole (15.0g, 0.52mol), 4-([1,1'-biphenyl]-4-yl)-2-chloro quinazoline ( 18.93g, 0.57mol after a) completely dissolved in 240ml xylene and sodium tert- butoxide (added 5.94g, 0.61mol), and bis (tri-tert-butylphosphine)palladium (0) (0.13g, 0.0026mol) It was heated and stirred for 2 hours and then insert. After concentrated under reduced pressure the xylene in the filtrate cooled to room temperature, remove the base and recrystallized from ethyl acetate, the compound 1-9: to produce a (19.84g, 93% yield).
  • 27
  • [ 1262866-93-2 ]
  • C34H22N2 [ No CAS ]
  • C54H34N4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With bis(tri-t-butylphosphine)palladium(0); sodium t-butanolate In 5,5-dimethyl-1,3-cyclohexadiene for 7h; Inert atmosphere; Heating; 10 1) Compounds 2-10 synthesized The compound 1-A in the atmosphere of nitrogen (19.8g, 0.43mol), complete the 2-chloro-4,6-diphenyl-1,3,5-triazine (12.67g, 0.47mol) and xylene (Xylene) 240ml after the sodium was dissolved -tert- butoxide (4.98g, 0.52mol) was added and the mixture was stirred under heating, bis (tri -tert- butylphosphine) palladium after loading (0.44g, 0.08mol) for 7 hours. After cooled to room temperature, filtered to remove salts and concentrated under reduced pressure and tetrahydrofuran: hexane = 1: 2 to 10 column was prepared by the compound to 5.
  • 28
  • [ 1262866-93-2 ]
  • [ 68716-49-4 ]
  • 4-([1,1'-biphenyl]-4-yl)-2-(4-bromophenyl)quinazoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,4-dioxane; water; at 120℃; for 3h; 4- (biphenyl-4-yl) -2-chloroquinazoline 10.0 g (31.6 mmol)andTo 9.8 g (34.7 mmol) of 2- (4-bromophenyl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane 200 mL of dioxane and 50 mL of distilled water were added. 1.8 g (1.6 mmol) of Pd (PPh3) 4 and 13.1 g (94.7 mmol) of K2CO3 were added, and the mixture was refluxed at 120 DEG C for 3 hours. The reaction mixture was cooled to room temperature and 500 mL of ammonium chloride aqueous solution was added to the reaction solution to terminate the reaction. The mixture was extracted with 500 mL of E.A and washed with distilled water. The obtained organic layer was dried over anhydrous MgSO 4, distilled under reduced pressure, and then purified by silica gel column chromatography to obtain the desired compound (10.8 g, yield 78%).
  • 29
  • [ 1262866-93-2 ]
  • [ 68716-49-4 ]
  • C46H30N4S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / 1,4-dioxane; water / 3 h / 120 °C 2: caesium carbonate; palladium diacetate; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane / toluene / 12 h / 120 °C
  • 30
  • [ 1262866-93-2 ]
  • C26H15NO [ No CAS ]
  • C46H27N3O [ No CAS ]
YieldReaction ConditionsOperation in experiment
71% With bis[tris( 1,1-dimethylethyl)phosphine]-palladium; sodium t-butanolate In 5,5-dimethyl-1,3-cyclohexadiene for 3h; Inert atmosphere; Heating; 5 Synthesis of compound 3-2-8 Compound 3-1 (11.86, 33.23mmol), in 500ml round bottom flask under nitrogen 4-([1,1'-biphenyl]-4-yl)-2-chloroquinazoline (10.00g, 31.65mmol) in a 210ml xylene after completely dissolved was added sodium tert-butoxide (3.95g, 41.14mol ) and, Bis(tri-tert -butylphosphine)palladium(0) (0.16g, 0.32mmol) was heated and stirred for 3 hours was placed. Was cooled down to room temperature and concentrated under reduced pressure to remove the base xylene was recrystallized from 250ml ethyl acetate to the compound 3-2-8 (14.42g, yield: 71%) was prepared.
  • 31
  • [ 1262866-93-2 ]
  • C36H33BO2 [ No CAS ]
  • C50H34N2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water at 80℃; for 12h; Inert atmosphere; 14 synthesis example 14: the composition of the compound 20. In the nitrogen ambient, after intermediate I-4s (13 g, 25.6 mmol) were melted in the THF 100 ml here intermediate I-6s (8.9 g, 28.1 mmol) and tetrakis(triphenylphosphine) palladium (Pd(PPh(sub)3(/sub))(sub)4(/sub)) (1.5 g, 1.28mmol) were put and it mixed. Saturated potassuim carbonate (K(sub)2(/sub)CO(sub)3(/sub)) (7 g, 51.1 mmol) were put in water and it heatedup in 80 for 12 hours and it refluxed.After water was put in into the reaction solution after the reactioncompletion and it extracted in the dichloromethane (DCM) moisture was removedto the anhydrous MgSO4 it filtered and it was concentrated under reducedpressure. The residue obtained in this way was refined to the flash columnchromatography after dividing and compound 20s (12.7 g, 75 %) were obtained.
  • 32
  • [ 607-68-1 ]
  • [ 144432-80-4 ]
  • [ 1262866-93-2 ]
YieldReaction ConditionsOperation in experiment
70% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; at 80℃; for 12h;Inert atmosphere; In the nitrogen ambient, after 2 -(biphenyl-4-yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolanes (20 g, 100 mmol) weremelted in the THF 1 L here 2,4-dichloroquinazolines (28.2 g, 100 mmol) andtetrakis (triphenylphosphine) palladium (Pd(PPh(sub)3(/sub))(sub)4(/sub)) (2.9g, 2.51 mmol) were put and it mixed. Saturated potassuim carbonate(K(sub)2(/sub)CO(sub)3(/sub)) (28 g, 200 mmol) were put in water and it heatedup in 80for 12 hours and it refluxed. After water was put in into the reaction solutionafter the reaction completion and it extracted in the dichloromethane(DCM) moisture was removed to the anhydrous MgSO4 it filtered and it wasconcentrated under reduced pressure. The residue obtained in this way wasrefined to the flash column chromatography after dividing and intermediate I-6s(22.3 g, 70 %) were obtained.
  • 33
  • [ 1262866-93-2 ]
  • C36H33BO2 [ No CAS ]
  • C50H34N2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water at 80℃; for 12h; Inert atmosphere; 16 synthesis example 16: the composition of the compound 74. In the nitrogen ambient, after intermediate I-8s(10 g, 19.6 mmol) were melted in the THF 100 ml here intermediate I-6s (6.85 g,21.6 mmol) and tetrakis (triphenylphosphine) palladium(Pd(PPh(sub)3(/sub))(sub)4(/sub)) (1.14 g, 0.98 mmol) were put and it mixed.Saturated potassuim carbonate (K(sub)2(/sub)CO(sub)3(/sub)) (5.4 g, 39.3 mmol)were put in water and it heated up in 80for 12 hours and it refluxed. After water was put in into the reaction solutionafter the reaction completion and it extracted in thedichloromethane (DCM) moisture was removed to the anhydrous MgSO4 it filteredand it was concentrated under reduced pressure. The residue obtained in thisway was refined to the flash column chromatography after dividing and compound 74 (11 g, 85 %) were obtained
  • 34
  • [ 1262866-93-2 ]
  • [ 1346007-12-2 ]
  • C50H32N2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water at 80℃; for 12h; Inert atmosphere; 17 synthesis example 17: the composition of the compound 128. In the nitrogen ambient, after intermediateI-10s (10 g, 19.8 mmol) were melted in the THF 100 ml here intermediate I-6s(6.88 g, 21.7 mmol) and tetrakis (triphenylphosphine) palladium(Pd(PPh(sub)3(/sub))(sub)4(/sub)) (1.14 g, 0.99 mmol) were put and it mixed.Saturated potassuim carbonate (K(sub)2(/sub)CO(sub)3(/sub)) (5.4 g, 39.5 mmol)were put in water and it heated up in 80for 12 hours and it refluxed. After water was put in into the reaction solution after the reaction completion and it extracted in thedichloromethane (DCM) moisture was removed to the anhydrous MgSO4it filtered and it was concentrated under reduced pressure. The residueobtained in this way was refined to the flash column chromatography afterdividing and compound 128 (10 g, 75 %) were obtained
  • 35
  • [ 1262866-93-2 ]
  • 8-(9-phenyl-9H-carbazole-3-yl)dibenzofuran-1-boronic acid [ No CAS ]
  • 3-[9-(4-biphenyl-4-yl-quinazolin-2-yl)-dibenzofuran-2-yl]-9-phenyl-9H-carbazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% With palladium diacetate; sodium carbonate; tris-(o-tolyl)phosphine In water for 16h; Reflux; m m) 3-[9-(4-biphenyl-4-yl-quinazolin-2-yI)-dibenzofuran-2-yI]-9-phenyl-9H-carbazole 49.8 g (110.0 mmol) of 8-(9-phenyl-9H-carbazol-3-yl)dibenzofuran-1 -boronic acid, 34 g (110.0 mmol) of 4-biphenyl-4-yI-2-chloroquinazoline and 26 g (210.0 mmol) of sodium carbonate are suspended in 500 ml of ethylene49.8 g (110.0 mmol) of 8-(9-phenyl-9H-carbazol-3-yl)dibenzofuran-1 -boronic acid, 34 g (110.0 mmol) of 4-biphenyl-4-yI-2-chloroquinazoline and 26 g (210.0 mmol) of sodium carbonate are suspended in 500 ml of ethylene glycol diamine ether and 500 ml of water. 913 mg (3.0 mmol) of tri-otolyiphosphine and then 112 mg (0.5 mmol) of palladium(ll) acetate are added to this suspension, and the reaction mixture is heated under reflux for 16 h. After cooling, the organic phase is separated off, filtered through silica gel, washed three times with 200 ml of water and subsequently evaporated to dryness. The product is purified by column chromatography on silica gel with toluene/heptane (1:2) and finally sublimed in a high vacuum (p = 5 x 10 mbar) (purity 99.9%). The yield is 60 g (87 mmol), corresponding to 80% of theory.
  • 36
  • [ 1133318-06-5 ]
  • [ 1262866-93-2 ]
  • C40H26N4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
91% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water for 5h; Inert atmosphere; Heating; 1 Example 1 Synthesis of Compound 2 Into a three-necked flask, Intermediate 2-2 (2 g, 4.9 mmol), Intermediate 2-3 (1.6 g, 4.9 mmol), potassium carbonate(0.1 g, 10 mmol), tetrakistriphenylphosphine palladium (0.1 g), tetrahydrofuran (50 ml) and water (20 ml). The mixture was heated under nitrogen for 5 hours, cooled, extracted with methylene chloride, dried and filtered. Column chromatography gave 2.5 g of product, 91% yield
  • 37
  • [ 1262866-93-2 ]
  • C35H21N [ No CAS ]
  • C55H33N3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% With potassium phosphate; bis(tri-t-butylphosphine)palladium(0) In 5,5-dimethyl-1,3-cyclohexadiene for 2h; Reflux; 5 Synthesis of Formula 2-2-2 10.0 g (21.9 mmol, 1.0 eq) of the formula 2-2-b, 7.6 g (24.1 mmol) of 4 - ([1,1'-biphenyl] -4-yl) -2-chloroquinazoline, K3PO4 9.3 g (43.9 mmol, 2.0 eq),) 0.05 g (0.10 mmol, 0.005 eq) of Pd (t-Bu3P) 2 was dissolved in xylene (Xylene), and the mixture was refluxed and stirred. When the reaction was completed after 2 hours, the solvent was removed by decompression. Then CHCl3 And the solvent was removed under reduced pressure. The resulting residue was subjected to column chromatography to obtain the compound of Formula 2-2-2 12.9 g (17.5 mmol, yield 80%).
  • 38
  • [ 1262866-93-2 ]
  • C24H14N2 [ No CAS ]
  • C44H26N4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% With potassium phosphate; bis(tri-t-butylphosphine)palladium(0) In 5,5-dimethyl-1,3-cyclohexadiene for 1h; Reflux; 7 synthesis of compound 1 - 61 Compound 1 10. 0 g (1. 0 eq), 4 - ([1, 1' a-biphenyl] provided 4 a-yl) - 2 a-chloroquinazoline 6. 13 g (1. 1 eq), K3 PO4 12. 86 g (2. 0 eq), Pd (t-a Bu3 P)2 0. 07 g (0. 005 eq) are agitated for 1 to 80 ml xylene (Xylene) refluxing the fronts. 1 reaction time was a stand-alone number to the end point of the pressure of the solvent. Then CHCl3 The base of the back pressure of the entire system to a stand-alone water good for a degree number was 50% solvent. In crystallinity was then heated with filtering Ethyl acetate through the main reflux again from each other. 1 - 61 same compound by column chromatography (14. 41g, yield 78%) are obtained.
  • 39
  • [ 1262866-93-2 ]
  • 5,8-dihydro-5-phenyl-5,8-diazaindeno[2,1-c]fluorene [ No CAS ]
  • 5-(4-([1,1'-biphenyl]-4-yl)quinazolin-2-yl)-8-phenyl-5,8-dihydroindolo[2,3-c]carbazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
77% Stage #1: 5,8-dihydro-5-phenyl-5,8-diazaindeno[2,1-c]fluorene With sodium hydride In N,N-dimethyl-formamide for 1h; Stage #2: 4-([1,1′-biphenyl]-4-yl)-2-chloroquinazoline In N,N-dimethyl-formamide at 20℃; Compound Cmp D-2 was synthesized A 3-necked round flask was charged with 5-phenyl-5,8-dihydroindolo [2,3-c] carbazole (5 g, 15.04 mmol).Anhydrous DMF (100 ml) was added to it.To this clear solution was added sodium hydride (1.203 g, 30.1 mmol).The resulting mixture was stirred for 1 hour.Then 4 - ([1,1'-biphenyl] -4-yl) -2-chloroquinazoline (5.72 g, 18.05 mmol)And the resulting mixture was stirred at room temperature overnight.The reaction mixture was quenched with ice / cold H 2 O (1.5 L).The resulting mixture was stirred for 30 minutes.The yellow solid was filtered and washed with H20 (1 L).The solid was dried, suspended in toluene (500 mL), heated, and stirred for 30 minutes. The suspension is warmed again and filtered.The solid was washed with toluene and passed through a plug of silica.This compound was suspended in DCM (100 mL) and acetone (250 mL).The suspension is heated and then stirred at room temperature overnight.It was filtered and washed with acetone (200 mL).The solid was dried under vacuum,5- (4 - ([1,1'-biphenyl] -4-yl) quinazolin- 2-yl) -8- phenyl- 5,8-dihydroindolo [2,3-c ] Carbazole (7.1 g, 77% yield, HPLC 99.99%).
  • 40
  • [ 1262866-93-2 ]
  • C22H15N [ No CAS ]
  • C42H27N3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
38% With dmap; potassium carbonate In N,N-dimethyl-formamide for 5h; Inert atmosphere; Reflux; 6 Synthesis of Compound 23 In a flask, Intermediate A (0.5 g, 1.7 mmol),2-Chloro-4-biphenylquinazoline(0.54 g, 1.7 mmol), potassium carbonate (0.23 g, 1.7 mmol),4-dimethylaminopyridine (0.5 g),DMF (10 mL),Heat to reflux under nitrogen for 5 hours, cool and remove the solvent. Purify the crude product by column chromatography to give 0.37 g. The yield is 38%
  • 41
  • [ 1262866-93-2 ]
  • C26H15N [ No CAS ]
  • C46H27N3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% With potassium phosphate; bis(tri-t-butylphosphine)palladium(0) In 5,5-dimethyl-1,3-cyclohexadiene for 3h; Reflux; 6 Synthesis Example 6. Synthesis of Compound 4-1-B 10.0 g (1.0 eq) of the formula 4-1,10.00 g (1.1 eq) of 4 - ([1,1'-biphenyl] -4-yl) -2-chloroquinazoline, 12.43 g (2.0 eq) of K3PO4, 0.07 g ) Was dissolved in 70 ml of xylene, refluxed and stirred. After 3 hours, the reaction was terminated and the solvent was distilled off. After that, it was completely dissolved in CHCl3, washed with water and decompressed again to remove about 50% of the solvent. Ethyl acetate was added in the refluxing state, and the crystals were dropped, cooled, and filtered. This was subjected to column chromatography to obtain 11.83 g (yield 65%) of the compound 4-1-B.
  • 42
  • [ 1262866-93-2 ]
  • C44H35BO2 [ No CAS ]
  • C58H36N2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water for 6h; Inert atmosphere; Reflux; 14 <Preparation Example 14> Preparation of Compound 14 After completely dissolving Compound B (10.0 g,16.49 mmol) and 4-al, 1’-biphenyl] -4-yl)-2-chloroquinazo-line (5.41 g, 14.99 mmol) in 380 ml of tetrahydrofuran in a500 ml round bottom flask under nitrogen atmosphere, a 2M aqueous potassium carbonate solution (190 ml) and thentetrakis-(triphenylphosphine)palladium (0.52 g, 0.45 mmol)were added thereto, and the result was heated and stirred for6 hours. Afier lowering the temperature to room tempera-tare, the water layer was removed, and the result was driedwith anhydrous magnesium sulfate, vacuum concentrated,and then recrystallized with 270 ml of ethyl acetate toprepare Compound 14 (11.25 g, yield: 85%). MS[M+H]=761
  • 43
  • [ 1262866-93-2 ]
  • C30H18N2O [ No CAS ]
  • C50H30N4O [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate; XPhos Inert atmosphere; Reflux; 34 Synthesis Example 27 (Synthesis of Compound 27) General procedure: In an argon atmosphere, 2.1 g of intermediate 8-A,1.54 g of 2-bromofluoranthene, 92 mg of tris(dibenzilideneacetone)dipalladium (0), 191 mg of 2,4,6-triisopropylbi- phenyl-2’-dicyclohexylphosphine, 673 mg of sodium teflbutoxide were placed in a 60 mE-flask and heated under reflux with stirring overnight. Alter cooling to room temperature (25° C.), the reaction solution was concentrated and residues were purified by silica gel chromatography, whereby 2.31 g (yield 74%) of yellow solids were obtained. As a result of an EC-MS analysis, the yellow solids were identified as compound 27.
  • 44
  • [ 1262866-93-2 ]
  • C30H18N2O [ No CAS ]
  • C50H30N4O [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% With tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate; XPhos Inert atmosphere; Reflux; 30 Synthesis Example 27 (Synthesis of Compound 27) General procedure: In an argon atmosphere, 2.1 g of intermediate 8-A,1.54 g of 2-bromofluoranthene, 92 mg of tris(dibenzilideneacetone)dipalladium (0), 191 mg of 2,4,6-triisopropylbi- phenyl-2’-dicyclohexylphosphine, 673 mg of sodium teflbutoxide were placed in a 60 mE-flask and heated under reflux with stirring overnight. Alter cooling to room temperature (25° C.), the reaction solution was concentrated and residues were purified by silica gel chromatography, whereby 2.31 g (yield 74%) of yellow solids were obtained. As a result of an EC-MS analysis, the yellow solids were identified as compound 27.
  • 45
  • [ 1262866-93-2 ]
  • [ 1679-18-1 ]
  • 4-([1,1'-biphenyl]-4-yl)-2-(4-chlorophenyl)quinazoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In water; toluene for 18h; Reflux; Inert atmosphere; 2 1 eq (24.2 g) of 4-(biphenyl-4-yl)-2-chloroquinazoline1 eq of 4-chlorophenylboronic acid (11.9 g)And 5 mol% of Pd (PP3) 4 (5.5 g)K2CO3 2eq (26.2g)Was dissolved in toluene (12 times of solid content, 320 ml)And distilled water (5 times the amount of K2CO3, 130 ml), And the mixture was stirred under reflux for 18 hours under a stream of nitrogen. After completion of the reaction, the reaction mixture was extracted with toluene and distilled water. The organic layer was dried over magnesium sulfate (MgSO4), filtered and the filtrate was concentrated under reduced pressure. The organic solution was removed, and the residue was subjected to silica gel column chromatography with hexane: dichloromethane = 8: 2 (v / v), and the resulting solid was recrystallized from dichloromethane and hexane to obtain 23.3 g of intermediate 3-b (Y = 78%).
  • 46
  • [ 1262866-93-2 ]
  • [ 1679-18-1 ]
  • C57H39N3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / toluene; water / 18 h / Reflux; Inert atmosphere 2: sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine / toluene / 18 h / Reflux
  • 47
  • [ 1262866-93-2 ]
  • 1-(dibenzo[b,d]furan-4-yl)-9H-carbazole [ No CAS ]
  • C44H27N3O [ No CAS ]
YieldReaction ConditionsOperation in experiment
14.6 g With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In 5,5-dimethyl-1,3-cyclohexadiene at 120℃; for 24h; 402 [Synthesis Example 373] Synthesis of Mat 373 General procedure: 250 mL of xylene was added to 5 g (14.99 mmol) of [Preparation Example 1] and 5.6 g (17.99 mmol) of 4-bromo-2,6-diphenylpyrimidine.0.68 g (0.75 mmol) of Pd2 (dba)3, 0.3 g (1.499 mmol) of P(t-Bu)3, 3.59 g (37.47 mol) of NaOtBu was added, and the mixture was refluxed at 120 to 24 hours. The reaction solution was cooled to room temperature and the reaction was terminated with 500 mL of an aqueous ammonium chloride solution. The mixture was extracted with 500 mL of M.C, and then washed with distilled water. The obtained organic layer was dried over anhydrous MgSO 4, distilled under reduced pressure, and purified by silica gel column chromatography to obtain 7.1 g (yield: 85%) of the desired compound.
  • 48
  • [ 1262866-93-2 ]
  • C16H10BrN [ No CAS ]
  • C53H35N3O [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate; tetrabutylammomium bromide / 1,4-dioxane; water / 6 h / 80 °C / Inert atmosphere 2: tetrakis(triphenylphosphine) palladium(0); sodium carbonate; tetrabutylammomium bromide / 1,4-dioxane; water / 6 h / 80 °C / Inert atmosphere
  • 49
  • [ 1262866-93-2 ]
  • C16H10BrN [ No CAS ]
  • C41H29N3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With tetrakis(triphenylphosphine) palladium(0); tetrabutylammomium bromide; sodium carbonate In 1,4-dioxane; water at 80℃; for 6h; Inert atmosphere; 10 Intermediate 1 - 87 - 5 synthesis of Under the environment of nitrogen, will (9.5 g, 30 mmol) intermediate 1 - 23 - 2, (12.3 g, 30 mmol) intermediate 1 - 80 - 4, (1.04 g, 0.6 mmol) four triphenyl phosphine palladium, (6.36 g, 60 mmol) sodium carbonate, (1.94 g, 6 mmol) tetrabutyl ammonium bromide, 150 ml of 1, 4 - dioxane and 30 ml water is added to a 500 ml three-opening in the bottle, heating 80 °C stirring for 6 hours, the end of the reaction, the reaction liquid inverted in 500 ml of pure water, the separated solid filtered, the filter residue recrystallization purification, to obtain intermediate 1 - 87 - 5, yield 70%.
  • 50
  • [ 1262866-93-2 ]
  • 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole [ No CAS ]
  • C44H27N3S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate; tetrabutylammomium bromide / 1,4-dioxane; water / 6 h / 80 °C / Inert atmosphere 2: copper(l) iodide; trans-1,2-cyclohexanediamine; potassium phosphate / toluene / 12 h / 110 °C / Inert atmosphere
  • 51
  • [ 1262866-93-2 ]
  • 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole [ No CAS ]
  • 4-(4-phenylphenylquinazolin-2-yl)carbazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% With tetrakis(triphenylphosphine) palladium(0); tetrabutylammomium bromide; sodium carbonate In 1,4-dioxane; water at 80℃; for 6h; Inert atmosphere; 5 Intermediate 1 - 23 - 3 synthesis of Under the environment of nitrogen, will (9.5 g, 30 mmol) intermediate 1 - 23 - 2, (8.79 g, 30 mmol) compound 1 - 3 - 5, (1.04 g, 0.6 mmol) four triphenyl phosphine palladium, (6.36 g, 60 mmol) sodium carbonate, (1.94 g, 6 mmol) tetrabutyl ammonium bromide, 150 ml of 1, 4 - dioxane and 30 ml water is added to a 500 ml three-opening in the bottle, heating 80 °C stirring for 6 hours, the end of the reaction, the reaction liquid inverted in 500 ml of pure water, the separated solid filtered, the filter residue recrystallization purification, to obtain intermediate 1 - 23 - 3, yield 65%.
  • 52
  • [ 1262866-93-2 ]
  • C35H23N [ No CAS ]
  • C55H35N3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
48% With palladium diacetate; sodium t-butanolate; XPhos In toluene for 15h; Inert atmosphere; 10 Method for synthesizing compound 3 General procedure: In the flask, intermediate C (2 g, 4.4 mmol), bromophenanthrene (1.4 g, 4.4 mmol), sodium t-butoxide (1 g, 10 mmol), palladium acetate (0.1 g), and X-phos (0.3 g) were sequentially added. ), toluene (30 mL), heated under reflux for 15 hours under nitrogen.After cooling, the solvent was removed, and the crude product was purified by column chromatography to afford product yield 76 %
  • 53
  • [ 1262866-93-2 ]
  • C39H31BO2 [ No CAS ]
  • C53H32N2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With tetrakis(triphenylphosphine) palladium(0); tetrabutylammomium bromide; sodium hydroxide In water; toluene at 80℃; for 12h; Inert atmosphere; 2.5 Under nitrogen, (16.3 g, 30 mmol) of compound 7-24-4 and (9.5 g, 30 mmol) of compound 7-24-7, (1.23g, 1.5mmol) tetrakis (triphenylphosphonium) palladium,(1.3 g, 4 mmol) tetrabutylammonium bromide,(1.6g, 40mmol) sodium hydroxide, (10mL) water and (80mL) toluene were added to a 250mL three-necked flask, and the reaction was heated at 80 ° C with stirring for 12 hours.The reaction solution should be evaporated by rotary evaporation to remove most of the solvent, and then washed 3 times with dichloromethane, and the organic solution was collected and mixed with silica gel.Purification was performed with a yield of 70%.
  • 54
  • [ 1262866-93-2 ]
  • C37H30BNO2S [ No CAS ]
  • C51H31N3S [ No CAS ]
YieldReaction ConditionsOperation in experiment
68% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran for 7h; Reflux; 16 General procedure: Compound P3 (10 g, 18 mmol) and 4-bromodibenzo[b,d]furan (4.4 g, 18 mmol) were added to 150 mL of tetrahydrofuran (THF).75 mL of 2M potassium carbonate (K2CO3) and 0.4 g of tetrakis (triphenylphosphine) palladium (Pd (PPh3) 4) were added, followed by stirring under reflux for 7 hours.After cooling to room temperature, the solid produced by filtration was recrystallized with chloroform and ethanol to prepare Compound 1 (7.7g, yield 73%,
  • 55
  • [ 1262866-93-2 ]
  • C37H30BNO3 [ No CAS ]
  • C51H31N3O [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran for 7h; Reflux; 5 General procedure: Compound P3 (10 g, 18 mmol) and 4-bromodibenzo[b,d]furan (4.4 g, 18 mmol) were added to 150 mL of tetrahydrofuran (THF).75 mL of 2M potassium carbonate (K2CO3) and 0.4 g of tetrakis (triphenylphosphine) palladium (Pd (PPh3) 4) were added, followed by stirring under reflux for 7 hours.After cooling to room temperature, the solid produced by filtration was recrystallized with chloroform and ethanol to prepare Compound 1 (7.7g, yield 73%,
  • 56
  • [ 1262866-93-2 ]
  • 2-bromo-9,9-dimethyl-9,10-dihydroacridine [ No CAS ]
  • C35H26BrN3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 2-bromo-9,9-dimethyl-9,10-dihydroacridine With sodium hydride In N,N-dimethyl-formamide at 60℃; for 1h; Inert atmosphere; Stage #2: 4-([1,1′-biphenyl]-4-yl)-2-chloroquinazoline In N,N-dimethyl-formamide at 120℃; for 12h; 9 Synthesis of Intermediate 9-3 Dissolve Intermediate 9-1 (17.3g, 60mmol) in 300ml of dry DMF, add NaH (1.67g), heat to 60 ° C in a nitrogen atmosphere and stir for 1 hour, then add the intermediate Body 9-2 (19.0 g, 60 mmol) was reacted at 120 ° C for 12 h.After cooling, the reaction solution was poured into water, the liquid was extracted and separated, and column chromatography was performed to obtain intermediate 9-3.
  • 57
  • [ 1262866-93-2 ]
  • C45H32N4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 60 °C / Inert atmosphere 1.2: 12 h / 120 °C 2.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / water; 1,4-dioxane / 12 h / 100 °C / Inert atmosphere 3.1: palladium diacetate; caesium carbonate; tricyclohexylphosphine / N,N-dimethyl-formamide / 12 h / Reflux; Inert atmosphere
  • 58
  • [ 1262866-93-2 ]
  • C45H33ClN4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 60 °C / Inert atmosphere 1.2: 12 h / 120 °C 2.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / water; 1,4-dioxane / 12 h / 100 °C / Inert atmosphere
  • 59
  • [ 1262866-93-2 ]
  • C17H11N3 [ No CAS ]
  • C37H23N5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% Stage #1: C17H11N3 With sodium hydride for 0.5h; Cooling with ice; Stage #2: 4-([1,1′-biphenyl]-4-yl)-2-chloroquinazoline for 2h; 2 Comp 4 Synthesis: Compound 8 (3 g, 11.7 mmol) was dissolved in about 40 mL of anhydrous N,N-dimethylacetamide and placed in an ice-water bath. Sodium hydride was added to the reaction solution step by step. After half an hour of reaction, a solution of compound 10 (3.7 g, 11.7 mmol) in N,N-dimethylacetamide was dropped into the reaction solution, stirred for 2 hours, and then slowly poured into ice water to quench it , Filtered and washed with solvent to obtain Comp-4 with a yield of 87%.
  • 60
  • [ 1262866-93-2 ]
  • C31H29BO4S [ No CAS ]
  • C45H30N2O2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water for 3h; Inert atmosphere; Reflux; 11 Preparation Example 11 Preparation of Compound 11 Compound A (7.54 g, 15.85 mmol) and a-11 (4.77 g, 15.09 mmol) were completely dissolved in 280 ml of tetrahydrofuran in a 500 ml round-bottom flask in a nitrogen atmosphere, and 2M aqueous potassium carbonate solution (140 ml) was added. , Tetrakis- (triphenylphosphine) palladium (0.52 g, 0.45 mmol) was added and then heated and stirred for 3 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from ethyl acetate 210 ml to prepare compound 11 (6.66 g, yield: 70%).
  • 61
  • [ 1262866-93-2 ]
  • C31H28BNO2 [ No CAS ]
  • C45H29N3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene at 110℃; for 6h; 13 Preparation of Compound 4 General procedure: After adding 2-bromo-4,6-diphenyl-1,3,5-triazine (8.2 g, 26.2 mmol), Pd(PPh3)4 (1.25 g, 1.09 mmol), K2CO3 (25.0 g, 65.4 mmol) and toluene/EtOH/H2O to Compound 1-5 (10.0 g, 21.8 mmol), the result was stirred for 6 hours at 110° C. After the reaction was completed, the result was cooled to room temperature, and extracted with distilled water and dichloromethane. After drying the organic layer with anhydrous MgSO4, the solvent was removed using a rotary evaporator, and with dichloromethane and hexane as a developing solvent, the result was purified using column chromatography to obtain target Compound 4 (10.4 g, 85%).
  • 62
  • [ 1262866-93-2 ]
  • C32H20N2S [ No CAS ]
  • C52H32N4S [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; XPhos In toluene for 24h; Inert atmosphere; Reflux; 1.4 (4) Synthesis of 1548 Take a 100 ml double-necked round bottom flask and put it into a stir bar and an upper reflux tube. After drying, it is filled with nitrogen. Intermediate 3-1548 (4.64 g, 0.01 mol) and raw material 4 ( 3.16g, 0.01mol), cesium carbonate (0.012mol), tris(dibenzylideneacetone)dipalladium (Pd2(dba)3, 0.5mmol) and 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (xphos, 0.55mmol), then toluene was added, the mixture was refluxed for 24 hours, after the reaction, cooled to room temperature, the reaction system was filtered and concentrated, and the crude product was purified by chromatography (ethyl acetate/n-hexane, 1 /10 (volume ratio)) to obtain compound 1548 (6.40 g, yield 86%).
  • 63
  • [ 1262866-93-2 ]
  • C48H34N2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / toluene; 1,4-dioxane; water / 12 h / 100 °C 2: potassium carbonate; copper; 18-crown-6 ether / 1,2-dichloro-benzene / 24 h / 180 °C
  • 64
  • [ 1262866-93-2 ]
  • C21H17NO [ No CAS ]
  • C41H29N3O [ No CAS ]
YieldReaction ConditionsOperation in experiment
66% Stage #1: C21H17NO With sodium hydride In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: 4-([1,1′-biphenyl]-4-yl)-2-chloroquinazoline In N,N-dimethyl-formamide for 1h; 8 7.0 g (23.382 mmol) of the compound represented by [Chemical Formula 7-c] obtained from [Scheme 18] and 0.84 g (35.074 mmol) of 60% sodium hydride were added to 70 ml of dimethylformamide and stirred at room temperature for 30 minutes. .Thereafter, 8.89 g (28.059 mmol) of [Chemical Formula 3-a] was dissolved in 100 mL of dimethylformamide, slowly added dropwise, and stirred for 1 hour.When the reaction was completed, 200 mL of distilled water was added, filtered, and recrystallized to obtain 9.0 g of a compound represented by [Chemical Formula 64].(Yield 66%)
  • 65
  • [ 1262866-93-2 ]
  • [ 5467-74-3 ]
  • 4-([1,1'-biphenyl]-4-yl)-2-(4-bromophenyl)quinazoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water; toluene at 100℃; for 12h; 11.1 Compound 5 g (13.39 mmol) represented by [Chemical Formula 3-a] obtained from [Scheme 8], 4-bromophenylboronic acid 3.25 g (16.07 mmol), tetrakis (triphenylphosphine) palladium 0.31 g (0.26 mmol), potassium carbonate 3.7 g (26.78 mmol), 1,4-dioxane 50 mL, toluene 50 mL, distilled water 50 mL, and stirred at 100° C. for 12 hours.When the reaction is completed, extraction is performed using ethyl acetate and distilled water.The organic layer was dried over anhydrous sodium sulfate, concentrated under reduced pressure, and recrystallized from methylene chloride and acetone to obtain 5.2 g of a compound represented by [Chemical Formula 11-a].(Yield 88%)
  • 66
  • [ 1262866-93-2 ]
  • C21H17NO [ No CAS ]
  • C41H29N3O [ No CAS ]
YieldReaction ConditionsOperation in experiment
44% Stage #1: C21H17NO With sodium hydride In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: 4-([1,1′-biphenyl]-4-yl)-2-chloroquinazoline In N,N-dimethyl-formamide for 1h; 3.2 7.0 g (23.382 mmol) of the compound represented by [Chemical Formula 1-d] obtained from [Scheme 4] and 0.84 g (35.074 mmol) of 60% sodium hydride were added to 70 mL of dimethylformamide and stirred at room temperature for 30 minutes. .Thereafter, 8.89 g (28.059 mmol) of [Chemical Formula 3-a] was dissolved in 100 mL of dimethylformamide, slowly added dropwise, and stirred for 1 hour.When the reaction was completed, 200 mL of distilled water was added, filtered, and recrystallized to obtain 6.0 g of the compound represented by [Chemical Formula 4].(Yield 44%)
  • 67
  • [ 1262866-93-2 ]
  • C24H13NO [ No CAS ]
  • C44H25N3O [ No CAS ]
YieldReaction ConditionsOperation in experiment
51% With bis(tri-t-butylphosphine)palladium(0); sodium t-butanolate In 5,5-dimethyl-1,3-cyclohexadiene for 2h; Reflux; Inert atmosphere; 13 Synthesis Example 13: Preparation of Compound 13 In a nitrogen atmosphere, sub 13 (10 g, 31.6 mmol), compound a (10.5 g, 31.6 mmol), and sodium tert-butoxide (6.1 g, 63.1 mmol) were added to 200 mL of xylene, followed by stirring and refluxing.After this, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added.After 2 hours, the reaction was terminated, cooled to room temperature, and reduced pressure to remove the solvent.Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure.The concentrated compound was purified by silica gel column chromatography to obtain 9.8 g of compound 13.(Yield 51%).
  • 68
  • [ 1262866-93-2 ]
  • C31H29BO3 [ No CAS ]
  • C45H30N2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
60% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water for 4h; Inert atmosphere; Reflux; 11 Preparation Example 11: Preparation of Compound 11 Intermediate A (7.50 g, 16.31 mmol) and Intermediate a-11 (4.91 g, 15.54 mmol) were completely dissolved in tetrahydrofuran (280 ml) in a 500 ml round bottom flask under a nitrogen atmosphere, to which a 2M aqueous potassium carbonate solution (140 ml) was added and tetrakis-(triphenylphosphine)palladium (0.54 g, 0.47 mmol) was added, and then the resulting mixture was heated and stirred for 4 hours. The temperature was lowered to normal temperature, the aqueous layer was removed, and the resulting product was dried over anhydrous magnesium sulfate then concentrated under reduced pressure, and recrystallized with ethyl acetate (230 ml) to prepare Compound 11 (5.97 g, yield: 60%). MS: [M+H]+=615
  • 69
  • [ 1262866-93-2 ]
  • 11'12-spiro[adamantane-2,12'-indeno[2,1-a]carbazole] [ No CAS ]
  • C48H37N3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
5.1 g With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In 5,5-dimethyl-1,3-cyclohexadiene at 120℃; for 24h; 46 [Synthesis Example 1] Synthesis of Compound 1 General procedure: Compound A synthesized in [Preparation Example 1]After adding 250 mL of xylene to 5.4 g (14.47 mmol) and 3.24 g (15.9 mmol) of Iodobenzene, Pd2 (dba) 30.79 g (0.86 mmol), P(t-Bu) 30.71 g (1.73 mmol), NaOtBu 3.47 After g (36.17 mol) was added, it was heated to reflux at 120°C for 24 hours. After cooling the temperature to room temperature, the reaction of the reaction solution was terminated with 500 mL of an aqueous ammonium chloride solution. The mixture was extracted with 500 mL of M.C, washed with distilled water, and then the obtained organic layer was dried over anhydrous MgSO 4, distilled under reduced pressure, and purified by silica gel column chromatography to obtain 5.2 g (yield 80%) of the title compound.
  • 70
  • [ 1262866-93-2 ]
  • C22H11NS [ No CAS ]
  • C42H23N3S [ No CAS ]
YieldReaction ConditionsOperation in experiment
53% With bis(tri-t-butylphosphine)palladium(0); sodium t-butanolate In 5,5-dimethyl-1,3-cyclohexadiene for 2h; Inert atmosphere; Reflux; 26 Synthesis Example 26 In a nitrogen atmosphere, compound sub 26 (10 g, 31.6 mmol), compound C (11.2 g, 34.7 mmol), and sodium tert-butoxide (NaOtBu, 6.1 g, 63.1 mmol) were added to 200 mL of Xylene, followed by stirring and refluxing. After this, bis(tri-tert-butylphosphine)palladium(0) [Pd(t-BuP3)2] (0.3 g, 0.6 mmol) was added. After 2 hours, the reaction was completed, cooled to room temperature, and reduced pressure to remove the solvent. Thereafter, the reaction product was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The thus concentrated compound was purified by silica gel column chromatography to obtain 10.1 g of compound 26. (Yield 53%)
  • 71
  • [ 1262866-93-2 ]
  • C24H14N2 [ No CAS ]
  • C44H26N4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
68% With potassium phosphate; bis(tri-t-butylphosphine)palladium(0) In 5,5-dimethyl-1,3-cyclohexadiene for 3h; Inert atmosphere; Reflux; 29 In a nitrogen atmosphere, formula A (10 g, 30.3 mmol), sub29 (10.5 g, 33.3 mmol), potassium phosphate (12.8 g, 60.5 mmol) was added to 200 ml of Xylene, and stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 2 hours, the reaction was terminated, cooled to room temperature, and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 12.6 g of sub29-a. (Yield 68%,
  • 72
  • [ 1262866-93-2 ]
  • C24H13NO [ No CAS ]
  • C44H25N3O [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate In N,N-dimethyl-formamide at 150℃; for 4h; 8 P213-C (10mmol), 2-chloro-4-(1,1'-biphenyl-4-yl)quinazoline (12mmol), potassium carbonate (15mmol), N,N-dimethylformamide 100mL It was added to the reaction flask, heated to 150° C. for 4 hours, and the reaction was completed by TLC monitoring. After cooling, the reaction was poured into water for filtration, and purified by filter cake column chromatography to obtain P213.
  • 73
  • [ 1262866-93-2 ]
  • [ 2796244-19-2 ]
  • [ 2796240-37-2 ]
YieldReaction ConditionsOperation in experiment
81% With tris-(dibenzylideneacetone)dipalladium(0); Cs2CO3; dicyclohexyl [2’,4’,6’-tris(propan-2-yl)-[1,1‘-biphenyl]-2-yl]phosphane In toluene for 12h; Inert atmosphere; Reflux; 1.6 (6) Synthesis of compound 2-31: take a 100-ml double-necked round-bottomed flask and put it into a stirring bar and a reflux tube, fill with nitrogen after drying, add intermediate 5-2-31 (3.19 g, 0.01 mol) ), raw material 3(3.16 g, 0.01 mol), cesium carbonate (0.015 mol), tris(dibenzylideneacetone)dipalladium (0.5 mmol) and2-Dicyclohexylphosphorus-2',4',6'-triisopropylbiphenyl (0.55mmol), then toluene was added, the mixture was refluxed for 12 hours, cooled to room temperature after the reaction, the reaction system was filtered and concentrated, the crude product Purified by chromatography (ethyl acetate/n-hexane, 1/10 (volume ratio)) to obtain compound 2-31 (4.85 g, yield 81%).
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