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[ CAS No. 532-18-3 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 532-18-3
Chemical Structure| 532-18-3
Chemical Structure| 532-18-3
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Product Details of [ 532-18-3 ]

CAS No. :532-18-3 MDL No. :MFCD03093264
Formula : C20H15N Boiling Point : -
Linear Structure Formula :- InChI Key :SBMXAWJSNIAHFR-UHFFFAOYSA-N
M.W : 269.34 Pubchem ID :68283
Synonyms :

Safety of [ 532-18-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 532-18-3 ]

* 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 [ 532-18-3 ]

[ 532-18-3 ] Synthesis Path-Downstream   1~87

  • 1
  • [ 503-74-2 ]
  • [ 532-18-3 ]
  • [ 10457-60-0 ]
YieldReaction ConditionsOperation in experiment
With zinc(II) chloride at 220℃;
  • 3
  • [ 532-18-3 ]
  • [ 857826-63-2 ]
YieldReaction ConditionsOperation in experiment
With arsenic trichloride; 1,2-dichloro-benzene
With arsenic trichloride; 1,1,2,2-tetrachloroethane
With arsenic trichloride at 200℃; beim Verschmelzen;
  • 4
  • [ 532-18-3 ]
  • [ 27825-28-1 ]
YieldReaction ConditionsOperation in experiment
With potassium permanganate
  • 5
  • [ 532-18-3 ]
  • [ 123-62-6 ]
  • 14-ethyl-dibenz[<i>a,j</i>]acridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With zinc(II) chloride at 220℃;
  • 7
  • [ 532-18-3 ]
  • [ 79-31-2 ]
  • [ 10457-59-7 ]
YieldReaction ConditionsOperation in experiment
With zinc(II) chloride at 220℃;
  • 8
  • [ 135-19-3 ]
  • [ 532-18-3 ]
YieldReaction ConditionsOperation in experiment
52% With palladium on activated carbon; ammonium formate; sodium formate; lithium hydroxide In m-xylene at 170℃; for 24h; Schlenk technique; Inert atmosphere;
50% With palladium on activated carbon; sodium formate; hydrazine hydrate; trifluoroacetic acid In toluene at 150℃; for 24h; Sealed tube; Inert atmosphere;
With ammonium chlorozincate at 280℃;
With ammonia; calcium chloride at 260 - 280℃;
With ammonium chlorozincate at 200 - 210℃;
Multi-step reaction with 2 steps 1: chlorocalciumammonia / 230 - 250 °C / dann auf 270-280grad 2: chlorocalciumammonia / 260 - 280 °C

  • 9
  • [ 135-19-3 ]
  • [ 532-18-3 ]
  • [ 91-59-8 ]
YieldReaction ConditionsOperation in experiment
With ammonium chlorozincate at 200 - 210℃;
With ammonia; calcium chloride at 230 - 250℃; dann auf 270-280grad;
  • 11
  • [ 135-19-3 ]
  • [ 532-18-3 ]
YieldReaction ConditionsOperation in experiment
With ammonium chloride; sodium acetate at 270℃;
  • 12
  • [ 580-13-2 ]
  • [ 532-18-3 ]
  • [ 91-59-8 ]
YieldReaction ConditionsOperation in experiment
69% With lithium amide In 1,2-dimethoxyethane at 80℃; for 20h;
69% Stage #1: 2-bromonaphthalene With lithium amide In 1,2-dimethoxyethane at 80℃; for 20h; Sealed vial; Stage #2: With hydrogenchloride In 1,2-dimethoxyethane; water at 20℃; for 0.0833333h; Stage #3: With sodium hydrogencarbonate In 1,2-dimethoxyethane; water 21 2-Bromonapthathene (0.207 g, 1.00 mmol), (CyPF-^-Bu)PdCl2 (7.30 mg, 1.00 x 10"2 mmol), and LiNH2 (0.230 g, 10.0 mmol) in 4.0 mL DME gave 0.100 g(69%) of 1-Aminonaphthalene as a solid (hexane/ethyl acetate: 70/30). 1H NMR(CDCl3) δ 7.67 (d, J= 8.4 Hz, 1 H), 7.63 (d, J= 8.4 Hz, 1 H), 7.57 (d, J= 8.0 Hz,1 H), 7.35 (td, J= 7.2, 1.2 Hz, 1 H), 7.21 (td, J= 7.2, 1.6 Hz, 1 H), 6.93 (s, 1 H),6.90 (dd, J = 8.4, 2.0 Hz, 1 H), 3.76 (s, br, 2 H); 13C NMR (CDCI3) δ 144.05, 134.83, 129.12, 127.86, 127.65, 126.27, 125.73, 122.38, 118.17, 108.48.
  • 13
  • [ 955107-51-4 ]
  • [ 532-18-3 ]
  • C66H46N2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% With tri-tert-butyl phosphine; sodium t-butanolate In toluene at 100℃; 1.1-3 In a stream of argon, 4 g (10 mmol) of 1,2-bis(4-(4'-chlorophenyl)phenyl)ethene, 5.4 g (25 mmol) of bis(2-naphthyl)amine, 0.03 g (1.5 mol %) of palladium acetate, 0.06 g (3 mol %) of tri-t-butylphosphine, 2.4 g (25 mmol) of t-butoxysodium, and 100 mL of dry toluene were added to a 300-mL three-necked flask provided with a cooling pipe, and then the whole was stirred under heat at 100° C. overnight. After the completion of the reaction, the precipitated crystal was taken by filtration, and was washed with 50 mL of toluene and 100 mL of methanol, whereby 6.1 g of a pale yellow powder were obtained. The powder was identified as Compound (D-2-2) (in 80% yield) by 1H-NMR spectroscopy and field desorption mass spectroscopy (FD-MS). It should be noted that the 1H-NMR spectrum of the compound was measured by using a DRX-500 (heavy methylene chloride solvent) manufactured by Brucker. The maximum absorption wavelength and maximum fluorescence wavelength of the resultant compound measured in a toluene solution were 389 nm and 445 nm, respectively.
  • 14
  • [ 532-18-3 ]
  • [ 194-59-2 ]
  • 15
  • [ 18869-30-2 ]
  • [ 532-18-3 ]
  • N,N,N',N'-tetra(2-naphthyl)-4,4'-diaminostilbene [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% With sodium t-butanolate;tri-tert-butyl phosphine; palladium diacetate; In toluene; at 20 - 115℃; [0106] (3) N,N,N?,N?-tetra(2-naphthyl)-4,4?-diaminostilbene was prepared. The reaction scheme is shown in the following: [0107] Into a 50 ml two-necked flask, 420 mg (1.56 mmol, 2.1 eq) of di-2-naphthylamine obtained in (2), 250 mg (0.741 mmol) of 4,4-dibromostilbene, 3.4 mg (0.0148 mmol, 2.0% by mole) of palladium acetate and 157 mg (1.63 mmol, 2.2 eq) of sodium t-butoxide were placed. A rubber cap was placed at the side opening of the flask. A coiled tube condenser for refluxing was attached to the central opening of the flask and a three-way stopcock attached with a balloon containing the argon gas was attached to the top of the coiled tube condenser. The atmosphere in the system was purged with the argon gas in the balloon 3 times using a vacuum pump. [0108] To the above system, 10 ml of dehydrated toluene and 13.4 ?l (0.0296 mmol, 4.0% by mole) of a 2.22 moles/liter toluene solution of tris-t-butylphosphine were added using a syringe through a rubber septum. Then, the flask was set into an oil bath and the temperature was raised slowly to 115 C. while the solution was stirred. Brownish white precipitates were formed in the reaction solution after 30 minutes. After heating at 115 C. for 6 hours under stirring, the flask was removed from the oil bath and left standing for one night. [0109] The formed precipitates were completely dissolved in 500 ml of dichloromethane. After the resultant fluid was transferred to a separation funnel and washed with 100 ml of a saturated aqueous solution of sodium chloride, the organic layer (yellow) was dried with anhydrous potassium carbonate. After filtration, the organic solvent was removed by distillation and 150 ml of toluene and 50 ml of ethanol were added to the obtained residue. After a drying tube was attached to the flask, the precipitates were dissolved to some degree by heating at 80 C. and the resultant mixture was slowly cooled to the room temperature. The crystals of the ivory color in the system were separated by filtration using a Kiriyama funnel. After the crystals were washed with small amounts of toluene and ethanol and dried at 60 C. for 3 hours in a vacuum drying chamber, 428 mg (0.600 mmol) of N,N,N?,N?-tetra(2-naphthyl)-4,4?-diaminostilbene was obtained at a yield of 81%. [0110] The results of the measurements of NMR and FD-MASS on the obtained N,N,N?,N?-tetra(2-naphthyl)-4,4?-diaminostilbene were as follows: [0111] NMR: ?90 MHz 6.9 to 7.9 (38H, m) [0112] FD-MASS: 714
  • 16
  • N,N-Di(2-naphthyl)benzylamine [ No CAS ]
  • [ 532-18-3 ]
YieldReaction ConditionsOperation in experiment
80% With hydrogen In ethanol; chloroform at 20℃; for 30h; 3.2 EXAMPLE 3 [0102] (2) Di-2-naphthylamine was prepared. The reaction scheme is shown in the following: [0103] Into a 300 ml single-necked flask, 1.18 g (3.28 mmol) of N,N-di(2-naphthyl)benzylamine obtained in (1) and 135 mg (10% by weight) of palladium-active carbon (the content of palladium: 10% by weight) were placed. To the resultant mixture, 100 ml of chloroform and 20 ml of ethanol were added and the substrate was dissolved. A stirrer rod having the shape of a rugby ball was placed into the flask. A three-way stopcock attached with a balloon (a gas bag) containing 2 liters of the hydrogen gas was attached to the flask and the inside of the flask system was purged with the hydrogen gas 10 times using a vacuum pump. The hydrogen gas in the decreased amount was replenished and the volume of the hydrogen gas was adjusted at 2 liters. The resultant fluid was vigorously stirred at the room temperature. After the fluid was stirred for the total time of 30 hours at the room temperature, 100 ml of dichloromethane was added and the catalyst was removed by filtration. The obtained solution was transferred to a separation funnel and washed with 50 ml of a saturated solution of sodium hydrogencarbonate. The organic layer was separated, dried with anhydrous potassium carbonate and filtered and the solvent was removed by distillation. To the obtained residue, 50 ml of toluene was added. A drying tube was attached to the flask and the temperature was raised to 85 C. to dissolve the residue. The recrystallization was conducted by slowly cooling the resultant solution to the room temperature while the flask was left standing for one night. The formed crystals were separated using a Kiriyama funnel and dried in vacuo at 50 C. and 710 mg (2.62 mmol) of di-2-naphthylamine was obtained at a yield of 80%. [0104] The result of the measurements of FD-MASS on the obtained di-2-naphthylamine was as follows: [0105] FD-MASS: 269
  • 17
  • [ 532-18-3 ]
  • [ 131222-99-6 ]
  • C58H38N2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
94% With tri-tert-butyl phosphine; sodium t-butanolate;palladium diacetate; In toluene; at 100℃; Under argon flow, <strong>[131222-99-6]6,12-dibromochrysene</strong> (3.8 g, 10 mmol), di-2-naphthylamine (6.7 g, 25 mmol), palladium acetate (0.03 g, 1.5 mol %), tri-t-butylphosphine (0.06 g, 3 mol %), t-butoxysodium (2.4 g, 25 mmol), and anhydrous toluene (100 mL) were added to a 300-mL three-neck flask equipped with a condenser, and the mixture was heated overnight at 100 C. with stirring. After completion of reaction, precipitated crystals were collected through filtration, followed by washing with toluene (50 mL) and methanol (100 mL), to thereby yield 7.2 g of a pale yellow powder. The powder was identified as compound (14) through an NMR spectrum (see FIG. 10) and an FD-MS (yield: 94%). The NMR spectrum was obtained under the same conditions as employed in Synthesis Example 1.
  • 18
  • [ 3001-15-8 ]
  • [ 532-18-3 ]
  • [ 910455-94-6 ]
YieldReaction ConditionsOperation in experiment
With copper; potassium carbonate In decalin at 200℃; for 144h;
  • 19
  • [ 872705-64-1 ]
  • [ 532-18-3 ]
  • C64H48N2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% With sodium t-butanolate In toluene at 100℃;
80% With sodium t-butanolate In toluene at 100℃; 3 In a stream of argon, 4.7 g (10 mmol) of Intermediate 5, 6.7 g (25 mmol) of bis(2-naphthyl)amine, 0.03 g (1.5 mol%) of palladium acetate, 0.06 g (3 mol%) of tri-t-butylphosphine, 2.4 g (25 mmol) of t-butoxysodium, and 100 mL of dry toluene were added to a 300-mL three-necked flask provided with a cooling pipe, and then the whole was stirred under heat at 100°C overnight. After the completion of the reaction, the precipitated crystal was taken by filtration, and was washed with 50 mL of toluene and 100 mL of methanol, whereby 6.7 g of a pale yellow powder were obtained (80% yield). The 1H-NMR spectrum and FD-MS spectrum of the resultant compound were measured, whereby the compound was identified as Compound (5). It should be noted that the 1H-NMR spectrum (see Fig. 1 and Table 1) was measured with a DRX-500 (heavy methylene chloride solvent) manufactured by Brucker. In addition,the maximum absorption wavelength and maximum fluorescent wavelength of the resultant compound measured in a toluene solution were 410 nm and 428 nm, respectively. [Table 1] Table 1 Peak No. Position Height (ppm) (%) 1 0.08 71.55 2 1.26 15.86 3 2.06 13.96 4 2.12 77.87 5 2.34 11.48 6 7.13 23.07 7 7.15 23.61 8 7.31 39.56 9 7.36 22.93 10 7.37 45.22 11 7.38 51.93 12 7.39 87.14 13 7.39 81.02 14 7.39 62.22 15 7.40 54.30 16 7.40 77.62 17 7.42 29.66 18 7.52 63.93 19 7.59 49.00 20 7.61 43.63 21 7.66 36.06 22 7.68 34.43 23 7.70 74.43 24 7.77 64.64 25 7.79 100.00 26 7.81 48.39
  • 20
  • [ 532-18-3 ]
  • [ 20870-38-6 ]
  • C58H50N2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
82% With sodium t-butanolate In toluene at 100℃;
  • 21
  • [ 914281-87-1 ]
  • [ 532-18-3 ]
  • C66H50N2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
94% With sodium t-butanolate In toluene at 100℃;
  • 22
  • [ 27973-29-1 ]
  • [ 532-18-3 ]
  • C56H36N2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With tri-tert-butyl phosphine; sodium t-butanolate In toluene at 100℃; 8 Preparation Example 8 (Synthesis of Compound (26)) Under the stream of argon, 3.6 g (10 mmole) of 1,6-dibromopyrene, 6.7 g (25 mmole) of di(2-naphthyl)amine, 0.03 g (1.5% by mole) of palladium acetate, 0.06 g (3% by mole) of tri-t-butylphosphine, 2.4 g (25 mmole) of t-butoxysodium and 100 ml of dry toluene were placed into a 300 ml three-necked flask equipped with a condenser, and the resultant mixture was heated at 100 C under stirring for one night. After the reaction was completed, the formed crystals were separated by filtration and washed with 50 ml of toluene and 100 ml of methanol, and 6.6 g of a light yellow powder substance was obtained. The obtained product was identified to be Compound (26) from the 1H-NMR spectrum (Figure 8) and by the measurement in accordance with FD-MS (the yield: 90%). The 1H-NMR spectrum was obtained under the same condition as that in Synthesis Example 1.
  • 23
  • [ 1025456-40-9 ]
  • [ 532-18-3 ]
  • [ 1025456-41-0 ]
YieldReaction ConditionsOperation in experiment
11% With sodium t-butanolate In toluene for 7h; Inert atmosphere; Reflux; 7 Synthesis Example 7 (Synthesis of Compound 4-3); Under an atmospheric argon gas, adding 0.10 ml (62 mass %, 0.30 mmol) of tri-t-butylphosphine / toluene solution into a suspension made by throwing 3.50 g (6.26 mmol) of 3-(3-bromophenyl)-7,12-diphenylbenzo[k]-fluoranthene, 2.53 g (9.39 mmol) of dinaphthalen-2-ylamine, 0.17 g (0.19 mmol) of tris(dibenzylideneacetone)dipalladium(II) and 0.90 g (9.39 mmol) of t-butoxy sodium into 30 ml of anhydrous toluene; the reaction was allowed to proceed under refluxing while heating for 7 h. Methanol was added to the reacted mixture, precipitated solids were separated by filtration and washed with methanol. The resultant solid was purified through column chromatography (silicagel : toluene). Further, the solid was recrystallized through toluene and methanol to obtain 0.52 g (yield: 11 %) of 3-(3-(dinaphthalen-2-ylamino)phenyl)-7,12-diphenylbenzo[k]fluoranthene (Compound 4-3). The measured results of FDMS analysis, ultraviolet absorption peak wavelength λmax (molar absorption coefficient ε) in toluene solution and fluorescent light emission peak wavelength (FL) about the resultant compound are described below. Further, measured result of 1H-NMR spectrum is shown in FIG. 7. FDMS, calcd for C58H37N=747, found m/z=747 (M+) UV(PhMe); λmax, 422nm (ε 4.28), FL (PhMe, λex=322nm); λmax, 461nm
  • 24
  • [ 532-18-3 ]
  • [ 1391999-36-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: copper(I) oxide / N,N-dimethyl acetamide / 72 h / 190 °C / Inert atmosphere 2: potassium <i>tert</i>-butylate / tetrahydrofuran / 8 h / 20 °C / Inert atmosphere
  • 25
  • [ 532-18-3 ]
  • [ 1391999-40-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: copper(I) oxide / N,N-dimethyl acetamide / 72 h / 190 °C / Inert atmosphere 2: potassium <i>tert</i>-butylate / tetrahydrofuran / 8 h / 20 °C / Inert atmosphere 3: trans-di(μ-acetato)bis[o-(di-o-tolylphosphino)benzyl]dipalladium(II); 2,6-di-tert-butyl-4-methyl-phenol; sodium carbonate / N,N-dimethyl acetamide / 24 h / 130 °C / Inert atmosphere
  • 26
  • [ 532-18-3 ]
  • [ 1391999-42-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: copper(I) oxide / N,N-dimethyl acetamide / 72 h / 190 °C / Inert atmosphere 2: potassium <i>tert</i>-butylate / tetrahydrofuran / 8 h / 20 °C / Inert atmosphere 3: trans-di(μ-acetato)bis[o-(di-o-tolylphosphino)benzyl]dipalladium(II); 2,6-di-tert-butyl-4-methyl-phenol; sodium carbonate / N,N-dimethyl acetamide / 24 h / 130 °C / Inert atmosphere 4: piperidine / acetonitrile / 24 h / 90 °C / Inert atmosphere
  • 27
  • [ 532-18-3 ]
  • [ 15164-44-0 ]
  • [ 445256-89-3 ]
YieldReaction ConditionsOperation in experiment
43% With copper(I) oxide In N,N-dimethyl acetamide at 190℃; for 72h; Inert atmosphere;
  • 28
  • [ 532-18-3 ]
  • [ 1392276-02-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 6 h / Reflux 2: oxalyl dichloride / dichloromethane / 20 °C
  • 29
  • [ 626-39-1 ]
  • [ 532-18-3 ]
  • [ 865-48-5 ]
  • [ 1300028-58-3 ]
YieldReaction ConditionsOperation in experiment
69% With triphenylphosphine In toluene 5 (5) (5) Synthesis of 5-bromo-N1,N1,N3,N3-tetra(naphthalen-2-yl)benzene-1,3-diamine 23.86 g of a product (yield: 69%) was obtained in the same manner as described in the synthesis method of intermediate 2-1 except that 1,3,5-tribromobenzene (15.74 g, 50 mmol), dinaphthalen-2-ylamine (26.934 g, 100 mmol), Pd2(dba)3 (2.75 g, 3 mmol), PPh3 (2.62 g, 10 mmol), NaOt-Bu (28.83 g, 300 mmol), and toluene (525 mL) were used.
  • 30
  • [ 3141-24-0 ]
  • [ 532-18-3 ]
  • [ 865-48-5 ]
  • [ 1300028-64-1 ]
YieldReaction ConditionsOperation in experiment
68% With triphenylphosphine;tris-(dibenzylideneacetone)dipalladium(0); In toluene; (11) Synthesis of 3-Bromo-N2,N2,N5,N5-tetra(naphthalen-2-yl)thiophene-2,5-diamine 23.7 g of a product (yield: 68%) was obtained in the same manner as described in the synthesis method of 2-1 except that <strong>[3141-24-0]2,3,5-tribromothiophene</strong> (16.04 g, 50 mmol), dinaphthalen-2-ylamine (26.94 g, 100 mmol), Pd2(dba)3 (2.75 g, 3 mmol), PPh3 (2.62 g, 10 mmol), NaOt-Bu (28.83 g, 300 mmol), and toluene (525 mL) were used.
  • 31
  • [ 532-18-3 ]
  • [5,15-dibromo-10,20-bis[3,4,5-tris(decyloxy)phenyl]porphyrinato]nickel(II) [ No CAS ]
  • [5,15-bis[3,4,5-tris(decyloxy)phenyl]-10,20-bis(2,2’-dinaphthylamino)porphyrinato]nickel(II) [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% Stage #1: 2,2'-dinaphthylamine; [5,15-dibromo-10,20-bis[3,4,5-tris(decyloxy)phenyl]porphyrinato]nickel(II) Schlenk technique; Stage #2: With 18-crown-6 ether; palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In tetrahydrofuran at 70℃; for 2.5h; Schlenk technique; Inert atmosphere;
  • 32
  • [ 532-18-3 ]
  • 3-bromo-8-diphenylamino-5,10-diphenyl-5,10-dihydroindolo[3,2-b]indole [ No CAS ]
  • N3,N3-di(naphthalen-2-yl)-N8,N8,5,10-tetraphenyl-5,10-dihydroindolo[3,2-b]indole-3,8-diamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
58% With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In toluene at 80℃; for 12h; Reflux; 4 Synthesis Example 4 Synthesis of Compound 43 of Formula 1 Synthesis Example 4 Synthesis of Compound 43 of Formula 1 (0189) (0190) Synthesis of Compound 43 of Formula 1 (0191) After dissolving 15.1 mg (0.017 mmol) of Pd2(dba)3 and 6.70 mg (0.033 mmol) of t-Bu3P in 10 ml of toluene to prepare a mixture, the mixture was agitated for 10 minutes at room temperature. Quantities of 1 g (1.654 mmol) of 3-bromo-8-diphenylamino-5,10-diphenyl-5,10-dihydroindolo[3,2-b]-indole, 445 mg (1.654 mmol) of N,N-di(2-naphthyl)amine, and 95 mg (0.992 mmol) of t-BuONa were added to the mixture, and the mixture was refluxed and agitated for 12 hours at a temperature of 80° C. Then, 20 ml of cold distilled water was added to the mixture, and the mixture was extracted using ethyl acetate. After drying the extracts using magnesium sulfate, the extracts were filtered, and the solvent was evaporated. Thereafter, 756 mg of compound 43 (N3,N3-di(naphthalen-2-yl)-N8,N8,5,10-tetraphenyl-5,10-dihydroindolo[3,2-b]indole-3,8-diamine) (yield 58%) was obtained through column chromatography. (0192) 1H NMR (300 MHz, CDCl3), d (ppm): 7.83-7.77 (2H, m), 7.75-7.67 (4H, m), 7.65-7.56 (6H, m), 7.52-7.47 (3H, m), 7.47-7.44 (1H, m), 7.43-7.32 (10H, m), 7.27-7.20 (6H, m), 7.15-7.05 (6H, m), 6.98-6.91 (2H, m) EI-MS, m/e, calcd for C58H40N4 792.33. found 792.35.
  • 33
  • [ 532-18-3 ]
  • C41H24F6O6S2 [ No CAS ]
  • C79H52N2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
45% With tris-(dibenzylideneacetone)dipalladium(0); tributylphosphine; sodium t-butanolate In 5,5-dimethyl-1,3-cyclohexadiene for 48h; Reflux; Inert atmosphere; 5 Synthesis of Compound II-7 A mixture of 7.4 g (9.3 mmole)product of Step 2, 7.5 g (28 mmole) of dinaphthalen-2-ylamine, 0.18 g (0.2 mmole)of pd2(dba)3, 0.08 g (0.4 mmole) of tri-tert-butylphosphine, 2.7 g (27.9 mmole) of sodium tert-butoxide and o-xylene 100 ml were refluxed under nitrogen for 48 hours. Then, the solution was filtered at 130° C. To receive the filtrate, the o-xylene was removed under reduced pressure from the filtrate. The organic layer was extracted with dichloromethane and water, dried with anhydrous magnesium sulfate, the solvent was removed and the residue was purified by column chromatography on silica(hexane-dichloromethane) to give 4.3 g of compound II-7 (45%). MS (m/z, FAB+): 1028.1; 1H NMR (CDCl3, 400 MHz): chemical shift (ppm) 9.14 (s, 2H), 8.94 (d, J=8.00 Hz, 2H), 8.82 (s, 2H), 8.67 (d, J=9.20 Hz, 2H), 8.47 (d, J=8.00 Hz, 2H), 8.21 (d, J=8.00 Hz, 4H), 7.987.91 (m, 2H), 7.777.48 (m, 20H), 7.297.14 (m, 4H), 7.087.00 (m, 6H), 1.82 (s, 6H).
  • 34
  • [ 580-13-2 ]
  • [ 91-59-8 ]
  • [ 532-18-3 ]
YieldReaction ConditionsOperation in experiment
85% With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; triphenylphosphine; sodium t-butanolate In toluene at 100℃; for 24h; I.1.3 synthesis of Sub 1-219 In round bottom flask Sub 1-2-1(3) (4.1g, 20mmol), Sub 1-2-2(3) (2.9g, 20mmol), Pd2 (dba) 3 (0.9g, 1mmol), PPh3 ( 0.5g, 2mmol), NaOt-Bu (5.8g, 60mmol), were added to toluene (210mL), respectively and refluxed under stirring for 24 hours at 100°C. The organic layer was dried and the ether was extracted with water over MgSO4 and concentrated to the resulting organic silicagel column and recrystallized 1-2(19) 4.6g (yield: 85%) was obtained.
With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In toluene for 24h; Reflux; General procedure: R1 amino compound and R2 Bromine compound200 mmol was added to a 1000 mL flask and Pd2 (dba) 3 (6 g, 14 mmol), P (t-Bu) 3 (1.4 g, 7 mmol) and NaOt-Bu (29.6 g, 300 mmol) And the mixture is refluxed with stirring for 24 hours. After the reaction was completed, the reaction mixture was extracted with ether and water. The organic layer was dried over MgSO 4 and concentrated. The resulting organic material was purified by silica gel column and recrystallized to obtain the product.
  • 35
  • [ 201230-82-2 ]
  • [ 532-18-3 ]
  • [ 105467-74-1 ]
YieldReaction ConditionsOperation in experiment
66% With di-tert-butyl peroxide; palladium dichloride In dimethyl sulfoxide at 100℃; for 24h; Schlenk technique; 15 Example 15 Was added in a dry Schlenk reaction tube Palladium chloride (0.025 mmol),Copper pentapentate (0.05 mmol),2,2-dinaphthylamine (0.25 mmol),The system was displaced three times under one atmosphere of carbon monoxide atmosphere.Then, the solvent was added successively to dry dimethylsulfoxide (1.0 mL)DTBP (0.75 mmol) and solvent dry dimethylsulfoxide (2.0 mL)The reaction was stopped at 100 ° C for 24 hours,After cooling to room temperature, ethyl acetate was added to the reaction system to quench the reaction, a saturated potassium carbonate solution (30.0 mL) was added, and the mixture was extracted with dichloromethane (20 × 3). The acridone derivative was isolated by column chromatography,Separation yield of 66%
66% With di-tert-butyl peroxide; copper(II) dipivaloate; palladium dichloride In dimethyl sulfoxide at 100℃; for 24h; Schlenk technique;
  • 36
  • [ 532-18-3 ]
  • C35H21Br [ No CAS ]
  • N-(naphth-2-yl)-N-(4-(13-phenyl-13H-benzo[4,5]indeno[1,2-a]acenaphthylen-13-yl)phenyl)naphthalen-2-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
64.08% With palladium diacetate; sodium t-butanolate; tri tert-butylphosphoniumtetrafluoroborate In toluene at 105 - 108℃; for 7h; Inert atmosphere; 3.4 (4) Preparation of compound 16: The compound VIII (10.4 g, 20.0 mmol) obtained in step (3), bis(2-naphthyl)amine (5.9 g, 22 mmol), sodium tert-butoxide (2.9 g, 30 mmol) and 200 g of toluene, under nitrogen protection, was added palladium acetate (135 mg, 0.6 mmol) and P(T-Bu)3·HBF4 (348 mg, 1.2 mmol) and reacted at 105 to 108 ° C for 7.0 hours while TLC followed the reaction. After completion of the reaction, adding 300 g of water to quench the reaction, the system layer, the use of washed organic phase, the organic phase decompression solvent to no fractions. The residue was then subjected to column chromatography with a mixture of petroleum ether and ethyl acetate. The volume ratio of petroleum ether to ethyl acetate was petroleum ether: ethyl acetate = 10: 1, 10.6 g of compound 17 was obtained, and further the crude product was sublimed in a chemical vapor deposition system at 320 ° C to give 9.1 g of a white solid powder was obtained in a yield of 64.08%.
  • 37
  • [ 532-18-3 ]
  • N-(2,5-dichloro-4-oxo-2,5-cyclohexadien-1-ylidene)-4-methylbenzenesulfonamide [ No CAS ]
  • C33H24Cl2N2O3S [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With (R)-3,3'-bis(2,4,6-triisopropylphenyl)binol phosphoric acid In dichloromethane at 25℃; for 12h; Inert atmosphere; Schlenk technique; enantioselective reaction;
  • 38
  • [ 532-18-3 ]
  • N-(2,5-dichloro-4-oxo-2,5-cyclohexadien-1-ylidene)-4-methylbenzenesulfonamide [ No CAS ]
  • C33H24Cl2N2O3S [ No CAS ]
YieldReaction ConditionsOperation in experiment
With diphenyl hydrogen phosphate In dichloromethane at 25℃; for 12h; Inert atmosphere; Schlenk technique;
  • 39
  • N-tosyl-2,5-dimethyl-1,4-benzoquinone monoimine [ No CAS ]
  • [ 532-18-3 ]
  • C35H30N2O3S [ No CAS ]
YieldReaction ConditionsOperation in experiment
With diphenyl hydrogen phosphate In dichloromethane at 25℃; for 12h; Inert atmosphere; Schlenk technique;
  • 40
  • N-tosyl-2,5-dimethyl-1,4-benzoquinone monoimine [ No CAS ]
  • [ 532-18-3 ]
  • C35H30N2O3S [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% With (R)-3,3'-bis(2,4,6-triisopropylphenyl)binol phosphoric acid In dichloromethane at 25℃; for 24h; Inert atmosphere; Schlenk technique; enantioselective reaction;
  • 41
  • [ 532-18-3 ]
  • [ 1232102-18-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: palladium diacetate; sodium t-butanolate / toluene / Reflux; Inert atmosphere 2.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C 2.2: 0.5 h / 20 °C
Multi-step reaction with 2 steps 1.1: sodium t-butanolate; palladium diacetate / toluene / Inert atmosphere; Reflux 2.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C 2.2: 0.5 h / 20 °C
Multi-step reaction with 2 steps 1.1: sodium t-butanolate; palladium diacetate / toluene / Reflux; Inert atmosphere 2.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C 2.2: 0.5 h / -78 - 20 °C
Multi-step reaction with 2 steps 1.1: sodium t-butanolate; palladium diacetate / toluene / Inert atmosphere; Reflux 2.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C 2.2: 0.5 h / 20 °C

  • 42
  • [ 532-18-3 ]
  • C44H29N3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: palladium diacetate; sodium t-butanolate / toluene / Reflux; Inert atmosphere 2.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C 2.2: 0.5 h / 20 °C 3.1: toluene-4-sulfonic acid hydrazide / toluene / 2 h / 80 °C 3.2: 5 h / 110 °C
  • 43
  • [ 589-87-7 ]
  • [ 532-18-3 ]
  • [ 690658-65-2 ]
YieldReaction ConditionsOperation in experiment
76% With palladium diacetate; sodium t-butanolate In toluene Reflux; Inert atmosphere; 2 Preparation of compound III-2 Compound I-2 (19.9 g, 73.8 mmol) was sequentially added to a round bottom flask.Compound II-2 (20.9 g, 73.8 mmol),t-BuONa (10.7 g, 111 mmol),Pd(OAc)2 (0.33 g, 1.47 mmol) and ultrasonically deoxygenated toluene (1.5 L),Reflux overnight under nitrogen,After the reaction solution was cooled, treated with ethyl acetate and water,The resulting organic layer was dried over MgSO4.The solvent was evaporated under reduced pressure to obtain a crude product of compound III-2. Using silica gel as a stationary phase and methylene chloride/hexane as an eluent, the crude product was subjected to column chromatography to give compound III-2 (23.8 g, 76%). .
75% With palladium diacetate; sodium t-butanolate In toluene Inert atmosphere; Reflux; 3 Preparation of compound III-3 Compound I-3 (19.9 g, 73.8 mmol) was sequentially added to a round bottom flask.Compound II-3 (20.9 g, 73.8 mmol),t-BuONa (10.7 g, 111 mmol),Pd(OAc)2 (0.33 g, 1.47 mmol) and ultrasonically deoxygenated toluene (1.5 L),Reflux overnight under nitrogen,After the reaction solution was cooled, treated with ethyl acetate and water,The resulting organic layer was dried over MgSO 4 and the solvent was evaporated under reduced pressure.The crude product of compound III-3 was obtained using silica gel as stationary phase and dichloromethane/hexane as eluent.The crude product was subjected to column chromatography to give Compound III-3 (23.5 g, 75%).
75% With palladium diacetate; sodium t-butanolate In toluene Reflux; Inert atmosphere; 2 Preparation of compound III-2 Compound I-2 (19.9 g, 73.8 mmol) was sequentially added to a round bottom flask.Compound II-2 (20.9 g,73.8mmol),t-BuONa (10.7 g, 111 mmol),Pd(OAc)2 (0.33 g, 1.47 mmol) and ultrasonically deoxygenated toluene (1.5 L),Reflux overnight under nitrogen,After the reaction solution was cooled, treated with ethyl acetate and water,The resulting organic layer was dried over MgSO4.Evaporate the solvent under reduced pressureThe crude compound III-2 was obtained,With silicone as the stationary phase,Dichloromethane/hexane as eluent,The crude product is subjected to column chromatography.Compound III-2 (23.5 g, 75%) was obtained.
75% With palladium diacetate; sodium t-butanolate In toluene Inert atmosphere; Reflux; 3 Preparation of compound III-3 Compound I-3 (19.9 g, 73.8 mmol), compound II-3 (20.9 g, 73.8 mmol) were sequentially added to a round bottom flask. t-BuONa (10.7 g, 111 mmol), Pd(OAc) 2 (0.33 g, 1.47 mmol), and ultrasonically deoxygenated toluene (1.5 L),After refluxing under nitrogen atmosphere, the reaction mixture was cooled, treated with ethyl acetate and water, and the organic layer was dried over MgSO4.The solvent was distilled off under reduced pressure to give a crude product of compound III-3 with silica gel as the stationary phase.Column chromatography of the crude product with dichloromethane/hexane as eluent afforded compound III-3 (23.5 g, 75%).
71% With 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0); potassium <i>tert</i>-butylate In toluene at 105℃; for 8h; Inert atmosphere; 3 Synthesis of compound 7 2,2"-Dinaphthylamine (5g, 18.5mmol), p-bromoiodobenzene (6.5g, 19.4mmol), d2(dba) 3 (200mg), dppf (110mg), potassium tert-butoxide (5.2g, 46.25mmol), placed in a double-necked flask; after changing the nitrogen for three times, add 40mL of anhydrous toluene; the reaction was carried out under nitrogen protection; after 8 hours of reaction at 105C, the reaction was completed and cooled to room temperature, and water/dichloromethane extraction, The organic layer was dried with anhydrous sodium sulfate, the solvent was spun off, and the crude product was subjected to column chromatography to obtain compound 7 with a mass of 5.7 g and a yield of 71%.

  • 44
  • [ 110435-98-8 ]
  • [ 532-18-3 ]
YieldReaction ConditionsOperation in experiment
77% With triethyl borane; sodium hydroxide In tert-butyl methyl ether at 80℃; for 6h; Inert atmosphere; Sealed tube; 17 Example 17, wherein the amide substrate is as follows: Under argon atmosphere,Firstly, NaOH and triethylboron are stirred to form a transparent clear solution at room temperature.The concentration is 1M/L;Then,The above triethylboron solution was successively treated with 10umol (2mol%),Amide substrate 5mmol,Triethoxysilane or polymethylhydrogensiloxane 15mmol,MTBE 2mL added to the 10mL sealed tube,It is heated and stirred in an 80°C oil bath for 6 hours.The reaction is over,Exposing the reaction to air quenching,The amine product is then separated directly by column chromatography.According to the results of column chromatography separation, when using triethoxysilane or polymethylhydrogensiloxane (PMHS),The yield of the target product was:
75% Stage #1: <i>N</i>,<i>N</i>-di-[2]naphthyl-acetamide With Triethoxysilane; sodium triethylborohydride In tert-butyl methyl ether at 80℃; for 6h; Stage #2: With hydrogenchloride In tert-butyl methyl ether; water at 20℃; for 1h; chemoselective reaction;
Multi-step reaction with 2 steps 1: potassium hydroxide; triethyl borane / tetrahydrofuran / 24 h / 25 °C / Inert atmosphere; Schlenk technique; Sealed tube 2: sodium hydroxide; water / tetrahydrofuran / 1 h / 25 °C / Inert atmosphere; Schlenk technique; Sealed tube
  • 45
  • [ 532-18-3 ]
  • C39H27N [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: sodium t-butanolate; palladium diacetate / toluene / Inert atmosphere; Reflux 2.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C 2.2: 0.5 h / 20 °C 3.1: toluene-4-sulfonic acid hydrazide / toluene / 2 h / 80 °C 3.2: 5 h / 110 °C
  • 46
  • [ 532-18-3 ]
  • C48H31N3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: sodium t-butanolate; palladium diacetate / toluene / Reflux; Inert atmosphere 2.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C 2.2: 0.5 h / -78 - 20 °C 3.1: toluene-4-sulfonic acid hydrazide / toluene / 2 h / 80 °C 3.2: 5 h / 110 °C
  • 47
  • [ 532-18-3 ]
  • [ 105946-82-5 ]
  • [ 897921-62-9 ]
YieldReaction ConditionsOperation in experiment
78% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium t-butanolate In toluene Inert atmosphere; Reflux; Sonication; 3 Example 2: Preparation of Intermediate A-3 Compound I-3 (19.9 g, 73.8 mmol), 4-bromo-4'-iodobiphenyl (26.5 g, 73.8 mmol), t-BuONa (10.7 g, 111 mmol), and Pd (dppf) were successively added to a round bottom flask. ) Cl 2 ·CH 2 Cl 2 (1.2 g, 1.47 mmol) and ultrasonically deoxygenated toluene (1.5L), and refluxed under nitrogen atmosphere overnight. After the reaction solution was cooled, it was treated with ethyl acetate and water. The organic layer was dried over MgSO 4 , and the solvent was evaporated under reduced pressure to give a crude product of Compound II-3. The silica gel was used as the stationary phase. Dichloromethan Column chromatography of the crude product with alkane/hexane as eluent afforded compound II-3 (25.1 g, 78%).
74% With palladium diacetate; sodium t-butanolate In toluene Inert atmosphere; Reflux; 5 Preparation of compound III-38 Compound I-38 (19.9 g, 73.8 mmol), compound II-38 (26.5 g, 73.8 mmol) were sequentially added to a round bottom flask. t-BuONa (10.7 g, 111 mmol), Pd(OAc) 2 (0.33 g, 1.47 mmol), and ultrasonically deoxygenated toluene (1.5 L),After refluxing under nitrogen, the reaction solution was cooled and treated with ethyl acetate and water.The resulting organic layer was dried over MgSO 4 and the solvent was evaporated under reduced pressure.The crude product of compound III-38 was obtained using silica gel as stationary phase and dichloromethane/hexane as eluent.The crude product was subjected to column chromatography to give compound III-38 (27.3 g, 74%).
  • 48
  • [ 532-18-3 ]
  • C55H37N7 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: sodium t-butanolate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / toluene / Inert atmosphere; Reflux; Sonication 2: sodium t-butanolate; ammonium hydroxide; tris-(dibenzylideneacetone)dipalladium(0) / 5,5-dimethyl-1,3-cyclohexadiene / 6 h / Inert atmosphere; Reflux; Sonication 3: sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine / toluene / Inert atmosphere; Reflux; Sonication 4: sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine / toluene / 6 h / Inert atmosphere; Reflux; Sonication
  • 49
  • [ 532-18-3 ]
  • C51H35N7 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: sodium t-butanolate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / toluene / Inert atmosphere; Reflux; Sonication 2: sodium t-butanolate; ammonium hydroxide; tris-(dibenzylideneacetone)dipalladium(0) / 5,5-dimethyl-1,3-cyclohexadiene / 6 h / Inert atmosphere; Reflux; Sonication 3: sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine / toluene / Inert atmosphere; Reflux; Sonication 4: sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine / toluene / 6 h / Inert atmosphere; Reflux; Sonication
  • 50
  • [ 532-18-3 ]
  • N,N-Di(β-naphthyl)-p-phenylendiamin [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium t-butanolate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / toluene / Inert atmosphere; Reflux; Sonication 2: sodium t-butanolate; ammonium hydroxide; tris-(dibenzylideneacetone)dipalladium(0) / 5,5-dimethyl-1,3-cyclohexadiene / 6 h / Inert atmosphere; Reflux; Sonication
  • 51
  • [ 532-18-3 ]
  • C42H30N2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: sodium t-butanolate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / toluene / Inert atmosphere; Reflux; Sonication 2: sodium t-butanolate; ammonium hydroxide; tris-(dibenzylideneacetone)dipalladium(0) / 5,5-dimethyl-1,3-cyclohexadiene / 6 h / Inert atmosphere; Reflux; Sonication 3: sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine / toluene / Inert atmosphere; Reflux; Sonication
  • 52
  • [ 532-18-3 ]
  • C38H28N2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: sodium t-butanolate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / toluene / Inert atmosphere; Reflux; Sonication 2: sodium t-butanolate; ammonium hydroxide; tris-(dibenzylideneacetone)dipalladium(0) / 5,5-dimethyl-1,3-cyclohexadiene / 6 h / Inert atmosphere; Reflux; Sonication 3: sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine / toluene / Inert atmosphere; Reflux; Sonication
  • 53
  • [ 532-18-3 ]
  • C42H33N [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: sodium t-butanolate; palladium diacetate / toluene / Inert atmosphere; Reflux 2.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C 2.2: 0.5 h / 20 °C 3.1: toluene-4-sulfonic acid hydrazide / toluene / 2 h / 80 °C 3.2: 5 h / 110 °C
  • 54
  • [ 532-18-3 ]
  • C32H24BNO2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sodium t-butanolate; palladium diacetate / toluene / Inert atmosphere; Reflux 2.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C 2.2: 0.5 h / 20 °C
  • 55
  • [ 532-18-3 ]
  • C48H37N [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: sodium t-butanolate; palladium diacetate / toluene / Inert atmosphere; Reflux 2.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C 2.2: 0.5 h / 20 °C 3.1: toluene-4-sulfonic acid hydrazide / toluene / 2 h / 80 °C 3.2: 5 h / 110 °C
  • 56
  • [ 532-18-3 ]
  • C24H20BrI [ No CAS ]
  • C44H34BrN [ No CAS ]
YieldReaction ConditionsOperation in experiment
77% With palladium diacetate; sodium t-butanolate In toluene Inert atmosphere; Reflux; 9 Preparation of compound III-62 Compound I-62 (19.9 g, 73.8 mmol), compound II-62 (38.0 g, 73.8 mmol) were sequentially added to a round bottom flask. t-BuONa (10.7 g, 111 mmol), Pd(OAc) 2 (0.33 g, 1.47 mmol), and ultrasonically deoxygenated toluene (1.5 L),After refluxing under nitrogen, the reaction solution was cooled and treated with ethyl acetate and water.The resulting organic layer was dried over MgSO 4 , and the solvent was evaporated under reduced pressure to give crude compound III-62.The crude product was subjected to column chromatography using silica gel as a stationary phase and dichloromethane/hexane as eluent to obtain Compound III-62 (37.3 g, 77%).
  • 57
  • [ 532-18-3 ]
  • C23H16BrP [ No CAS ]
  • C43H30NP [ No CAS ]
YieldReaction ConditionsOperation in experiment
8% With Ni2(N,N-bis(2,6-diisopropylphenyl)imidazol-2-ylidene)2(μ-Br)2; triphenylphosphine; sodium t-butanolate In toluene at 80℃; for 24h; Inert atmosphere; Glovebox;
  • 58
  • [ 532-18-3 ]
  • C32H18Cl2N2 [ No CAS ]
  • C72H46N4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
7.45 g With palladium diacetate; triphenylphosphine; sodium t-butanolate In toluene at 80℃; for 8h; Inert atmosphere; 1 13.59 g (40 mmol) of intermediate B1-1,11.32 g (40 mmol) of intermediate C1'-1, 0.93 g (0.8 mmol)Tetrakis(triphenylphosphine)palladium, 115 ml of toluene,56 ml of sodium carbonate aqueous solution (2 M) was added to the flask, and the reaction was refluxed for 8 hours.After cooling to room temperature, it was extracted with toluene, and the organic phase was washed with brine.Drying and purifying by column chromatography gave 15.24 g (30.4 mmol) of Intermediate D1-1. Under an argon atmosphere, 5.01 g (10 mmol) of intermediate D1-1, 5.39 g (20 mmol) of 2,2-dinaphthylamine, 3.84 g (40 mmol) of sodium t-butoxide were dissolved in 200 ml of dehydrated toluene, and 0.05 g was added with stirring. (0.2 mmol) palladium acetate, 0.04 g (0.2 mmol) of triphenylphosphine, and the mixture was heated to 80 ° C for 8 hours. After cooling, it was filtered through a Celite/silica gel funnel, and the solvent was evaporated to remove the solvent, and the residue was crystallized from toluene to afford 7.45 g (7.7 mmol) of Compound GH4, yield 77%.
  • 59
  • [ 532-18-3 ]
  • C26H16BrN3 [ No CAS ]
  • C46H30N4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In toluene for 24h; Reflux; Sub 1 (16.9 g, 100 mmol) and Sub 2 (156 g, 50 mmol)Was dissolved in toluene (1000 mL)Pd2(dba)3 (3 g, 7 mmol), P(t-Bu)3 (0.7 g, 3.5 mmol) and NaOt-Bu (14.8 g, 150 mmol) were added and the mixture was refluxed for 24 hours. After the reaction was completed, the reaction mixture was extracted with ether and water. The organic layer was dried over MgSO 4 and concentrated. The resulting organic material was purified by silica gel column and recrystallized.
  • 60
  • [ 532-18-3 ]
  • C29H19Br [ No CAS ]
  • C49H33N [ No CAS ]
YieldReaction ConditionsOperation in experiment
74% With tri-tert-butyl phosphine; sodium t-butanolate In toluene Inert atmosphere; A9 Embodiment A9: A method for preparing an organic light compound having a structure as shown in the above P9, wherein the preparation method is as follows: Under nitrogen, 25.0 g, 55.89 mmol of intermediate formula 2-1, 16.56 g, 61.48 mmol of intermediate formula 3-9, 500 mL of anhydrous toluene were added to the reaction vessel, and the mixture was added under nitrogen atmosphere. 0.51 g, 0.56 mmol of palladium catalyst, tetrakis(triphenylphosphine)palladium Pd(PPh3)4, 21.46 g, 223.56 mmol of sodium t-butoxide and 0.23 g, 1.12 mmol of tri-tert-butylphosphine, completely replaced with air by nitrogen, heating up to 100 °C, overnight reaction. After the completion of the reaction, the reaction solution was cooled to room temperature, and the palladium catalyst was removed with celite, and water and dichloromethane were combined, and the organic phase was combined, dried over anhydrous magnesium sulfate, and evaporated. Purification of compounds shown 27.34g P9 by silica gel column chromatography, 77%.
  • 61
  • [ 532-18-3 ]
  • C7H4(2)H3BrIN [ No CAS ]
  • C27H18(2)H3BrN2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% Stage #1: 2,2'-dinaphthylamine With tetrakis(triphenylphosphine) palladium(0); sodium t-butanolate In toluene for 1h; Inert atmosphere; Reflux; Stage #2: C7H4(2)H3BrIN In toluene for 2h; Inert atmosphere; Reflux; 2-3 Preparation Example 2-3 Synthesis of Compound 2-C Di (naphthalen-2-yl) amine (32.3 g, 0.12 mol) completely dissolved in 240 mL of toluene in a nitrogen atmosphere, followed by sodium tert-butoxide (23.1 g, 0.24 mol), tetrakistriphenylphosphinepalladium (5.5 g 4.8 mmol) was added and refluxed for 1 hour and stirred. During reflux, Compound 1-C (37.8 g, 0.12 mol) was dissolved in 120 mL of toluene, slowly dropped, and then refluxed and stirred for 2 hours. After the reaction was completed, the organic layer was extracted with water, and then the organic layer was completely distilled and purified by column chromatography (chloroform / hexane) to prepare the compound 2-C (45.4 g, yield: 83%).
  • 62
  • [ 532-18-3 ]
  • [ 71757-16-9 ]
  • C26H18BrClN2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% Stage #1: 2,2'-dinaphthylamine With tetrakis(triphenylphosphine) palladium(0); sodium t-butanolate In toluene for 1h; Inert atmosphere; Reflux; Stage #2: 2-bromo-4-chloro-6-iodoaniline In toluene for 2h; Inert atmosphere; Reflux; 2-4 Preparation Example 2-4: Synthesis of Compound 2-D Di (naphthalen-2-yl) amine (32.3 g, 0.12 mol) completely dissolved in 240 mL of toluene in a nitrogen atmosphere, followed by sodium tert-butoxide (23.1 g, 0.24 mol), tetrakistriphenylphosphinepalladium (5.5 g 4.8 mmol) was added and refluxed for 1 hour and stirred. During the reflux, compound 1-D (39.9 g, 0.12 mol) was dissolved in 120 mL of toluene, slowly dropped, and refluxed and stirred for 2 hours. After the reaction was completed, the organic layer was extracted with water, and then the organic layer was completely distilled and purified by column chromatography (chloroform / hexane) to prepare the compound 2-D (46.1 g, yield: 81%).
  • 63
  • [ 532-18-3 ]
  • [ 84483-27-2 ]
  • C26H19BrN2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
82% Stage #1: 2,2'-dinaphthylamine With tetrakis(triphenylphosphine) palladium(0); sodium t-butanolate In toluene for 1h; Inert atmosphere; Reflux; Stage #2: 2-bromo-6-iodobenzenamine In toluene for 2h; Inert atmosphere; Reflux; 2-1 Preparation Example 2-1 Synthesis of Compound 2-A Di (naphthalen-2-yl) amine (32.3 g, 0.12 mol) completely dissolved in 240 mL of toluene in a nitrogen atmosphere, followed by sodium tert-butoxide (23.1 g, 0.24 mol), tetrakistriphenylphosphinepalladium (5.5 g 4.8 mmol) was added and refluxed for 1 hour and stirred. During reflux, compound 1-A (35.7 g, 0.12 mol) was dissolved in 120 mL of toluene, slowly dropped, and then refluxed and stirred for 2 hours. After the reaction was completed, the organic layer was extracted with water, and then the organic layer was completely distilled and purified by column chromatography (chloroform / hexane) to prepare the compound 2-A (43.2 g, yield: 82%).
  • 64
  • [ 532-18-3 ]
  • [ 289038-12-6 ]
  • C27H21BrN2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% Stage #1: 2,2'-dinaphthylamine With tetrakis(triphenylphosphine) palladium(0); sodium t-butanolate In toluene for 1h; Inert atmosphere; Reflux; Stage #2: 2-bromo-6-iodo-4-methylaniline In toluene for 2h; Inert atmosphere; Reflux; 2-2 Preparation Example 2-2: Synthesis of Compound 2-B Di (naphthalen-2-yl) amine (32.3 g, 0.12 mol) completely dissolved in 240 mL of toluene in a nitrogen atmosphere, followed by sodium tert-butoxide (23.1 g, 0.24 mol), tetrakistriphenylphosphinepalladium (5.5 g 4.8 mmol) was added and refluxed for 1 hour and stirred. During the reflux, compound 1-B (37.4 g, 0.12 mol) was dissolved in 120 mL of toluene, slowly dropped, and then refluxed and stirred for 2 hours. After the reaction was completed, the organic layer was extracted with water, and then the organic layer was completely distilled to purify with column chromatography (chloroform / hexane) to give the compound 2-B (43.5 g, yield: 80%).
  • 65
  • [ 91-58-7 ]
  • [ 532-18-3 ]
  • 66
  • [ 532-18-3 ]
  • C22H8Br2Cl2O2 [ No CAS ]
  • C62H36Cl2N2O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
73% Stage #1: 2,2'-dinaphthylamine; C22H8Br2Cl2O2 With sodium t-butanolate In toluene for 0.5h; Reflux; Stage #2: With tetrakis(triphenylphosphine) palladium(0) In toluene for 3h; Reflux; Synthesis of Compound 14 10.7 g (20 mmol) of Compound 3-A, 100 mmol of sodium-t-butoxide, 40 mmol of di(naphthalen-2-yl)amine and 200 mL of toluene were mixed, refluxed, heated for 30 minutes, 0.2 mmol of tetrakistriphenylphosphinepalladium was added, followed by stirring for 3 hours in a reflux state. After the reaction, the reaction solution was returned to room temperature, extracted with water, and the organic layer was recrystallized twice with chloroform to obtain 13.3 g of compound 4-L (yield 73%).
  • 67
  • [ 532-18-3 ]
  • C30H19N [ No CAS ]
YieldReaction ConditionsOperation in experiment
54% With acetic acid; silver(l) oxide In toluene at 60℃; for 2h; Sealed tube;
  • 68
  • [ 532-18-3 ]
  • 6-bromo-10,10-dimethyl-10H-indeno[2,1-b]triphenylene [ No CAS ]
  • C47H33N [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In toluene at 90℃; for 24h; Inert atmosphere; 22 Synthesis Example 1: Synthesis of Compound 2-bromo-7-(2-(methylsulfinyl)phenyl)triphenylene General procedure: Under a nitrogen stream 2- (7-bromotriphenylen-2-yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane 5.0 g (11.54 mmol) And 1.78 g (12.70 mmol) of 1-bromo-2- (methylsulfinyl) benzene Was dissolved in 75 ml of toluene, 2M K 2 CO 3 (8 ml) was added thereto, the gas was removed, and 0.73 g of Pd (PPh 3) 4 (5 mol%) was added thereto, followed by stirring at 90 ° C. for 24 hours. After cooling to room temperature, extracted with dichloromethane, water was removed with MgSO4 and separated into columns using EA / Hexane (1: 3) 2-bromo-7- (2- (methylsulfinyl) phenyl) triphenylene 3.49 g (yield 68%) were obtained.
  • 69
  • [ 532-18-3 ]
  • 6-(3-bromo-2-chlorophenoxy)-9,9-dimethyl-N,N-diphenyl-9H-fluorene-2-amine [ No CAS ]
  • 6-(2-chloro-3-(di(naphthalene-2-yl)amino)phenoxy)-9,9-dimethyl-N,N-diphenyl-9H-fluorene-2-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
34.7 g With bis(di-tert-​butyl(4-​dimethylaminophenyl)​phosphine)​dichloropalladium(II); sodium t-butanolate In 5,5-dimethyl-1,3-cyclohexadiene at 85℃; for 2h; Inert atmosphere; 8 Under nitrogen environment, For the addition of 6-(3-bromo-2-chlorophenoxy)-9,9-dimethyl-N,N-diphenyl-9H-fluoren-2-amine (32.7 g), Di(naphthalen-2-yl)amine (15.5 g), Pd-132 (Johnson Matthey) (1.2 g), NaOtBu (13.9 g) and xylene (160 ml) flasks are heated, It was stirred at 85 ° C for 2 hours. After cooling the reaction solution to room temperature, Add water and toluene for liquid separation, After refining the organic layer with a silicone short-range column (dissolved solution: toluene), Refined with a silicone column (dissolved solution: toluene / heptane = 1/3 (volume ratio)), Thus, 6-(2-chloro-3-(bis(naphthalen-2-yl)amino)phenoxy)-9,9-dimethyl-N,N-diphenyl-9H-fluoren-2-amine (34.7 g).
34.7 g With bis(di-tert-​butyl(4-​dimethylaminophenyl)​phosphine)​dichloropalladium(II); sodium t-butanolate In 5,5-dimethyl-1,3-cyclohexadiene at 85℃; for 2h; Inert atmosphere; 6 Synthesis of compound (1C-1) In a nitrogen atmosphere, a flask containing 6-(3-bromo-2-chlorophenoxy)-9,9-dimethyl-N,N-diphenyl-9H-fluorene-2-amine (32.7 g), di(naphthalene-2-yl)amine (15.5 g), Pd-132 (Johnson Massey) (1.2 g), NaOtBu (13.9 g) and xylene (160 ml) was heated and stirred at 85° C. for 2 hours. The reaction liquid was cooled to room temperature, water and toluene were added thereto, and the solution was partitioned. The solvent of the organic layer was purified by silica gel short pass column (eluent: toluene), and then purified by silica gel column (eluent: toluene/heptane=1/3 (volume ratio)) to obtain 6-(2-chloro-3-(di(naphthalene-2-yl)amino)phenoxy)-9,9-dimethyl-N,N-diphenyl-9H-fluorene-2-amine (34.7 g).
  • 70
  • [ 532-18-3 ]
  • C22H16Cl2N2 [ No CAS ]
  • C62H44N4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tri-tert-butyl phosphine; potassium <i>tert</i>-butylate; palladium diacetate In toluene at 80 - 120℃; for 4h; Inert atmosphere; 3 General procedure: Take a 1L three-necked flask, equip with magnetic stirring, and add potassium tert-butoxide (33.6g, 0.3mol), diphenylamine (50.7g, 0.3mol) and 400ml of toluene after nitrogen replacement.After replacing with nitrogen again, (1.2 g, 6 mmol) tri-tert-butyl phosphine and (0.7 g, 3 mmol) palladium acetate were sequentially added.After the addition, heat to 85°C.Start dropping a solution consisting of (40.2g, 0.1mol) M1 and 100ml toluene,The temperature is controlled at 80-120°C for 4 hours to complete the reaction.Adjust to neutral, separate the organic phase, extract, dry, column chromatography, spin-dry the solvent,60.8 g of light yellow solid was obtained,The yield is about 75%
  • 71
  • [ 532-18-3 ]
  • C19H10Cl2N2S [ No CAS ]
  • C59H38N4S [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% With tri-tert-butyl phosphine; potassium <i>tert</i>-butylate; palladium diacetate In toluene at 80 - 120℃; for 4h; Inert atmosphere; 14 Synthesis of Compound I-12 General procedure: A 1L three-necked flask equipped with magnetic stirring. After nitrogen replacement, potassium tert-butoxide (33.6g, 0.3mol), diphenylamine (50.7g, 0.3mol) and 400ml of toluene were added in sequence.After replacing with nitrogen again, (1.2 g, 6 mmol) tri-tert-butyl phosphine and (0.7 g, 3 mmol) palladium acetate were sequentially added. After the addition, heat to 85°C.Start dropping a solution consisting of (40.2g, 0.1mol) M1 and 100ml toluene,The temperature is controlled at 80-120°C for 4 hours and the reaction is over. Adjust to neutral, separate the organic phase,Extraction, drying, column chromatography, and spin-drying solvent to obtain 60.1 g of light yellow solid with a yield of about 75%.
  • 72
  • C26H26BNO2 [ No CAS ]
  • [ 532-18-3 ]
YieldReaction ConditionsOperation in experiment
0.25 g With water; sodium hydroxide In tetrahydrofuran at 25℃; for 1h; Inert atmosphere; Schlenk technique; Sealed tube;
  • 73
  • [ 532-18-3 ]
  • C19H10Cl2N2O2S [ No CAS ]
  • C59H38N4O2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
79% With tri-tert-butyl phosphine; potassium <i>tert</i>-butylate; palladium diacetate In toluene at 80 - 120℃; for 4h; Inert atmosphere; 3 Synthesis of compound I-6 General procedure: Take a 1L three-necked flask with magnetic stirring, add potassium tert-butoxide (33.6g, 0.3mol), Diphenylamine (50.7g, 0.3mol) and 400ml of toluene. After replacing with nitrogen again, (1.2 g, 6 mmol) tri-tert-butyl phosphine and (0.7 g, 3 mmol) palladium acetate were sequentially added. After the addition, heat to 85°C, and then start to add (43.4g, 0.1mol) M1 and A solution composed of 100ml of toluene is reacted at 80-120°C for 4 hours at a temperature controlled, and the reaction is complete. Adjust to neutral, separate the organic phase, extract, dry, column chromatography, spin-dry the solvent, Obtain 62.5 g of light yellow solid with a yield of about 75%.
  • 74
  • [ 532-18-3 ]
  • C12H8BrClO [ No CAS ]
  • C32H22ClNO [ No CAS ]
YieldReaction ConditionsOperation in experiment
83.71% With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In toluene at 90℃; for 5h; Inert atmosphere; 1.2 2. Under the protection of nitrogen, dissolve Intermediate 1 (24.69mmol) and raw material C1-3 (24.69mmol) in 140.00ml of toluene solution,Add tris(dibenzylideneacetone)dipalladium (0.25mmol), tri-tert-butylphosphine (1.23mmol) and sodium tert-butoxide (49.38mmol), stir evenly, heat to 90°C, and react under reflux for 5h;After the reaction, the temperature was lowered slightly, and the diatomaceous earth was used to filter to remove the salt and catalyst. After the filtrate was cooled to room temperature, it was washed three times with water, and the organic phase was retained. Then the aqueous phase was extracted with ethyl acetate; Water magnesium sulfate for drying,A solid was obtained, and intermediate 2-1 was prepared; (9.75g, yield: 83.71%);
  • 75
  • [ 532-18-3 ]
  • C40H22ClNO [ No CAS ]
  • C60H36N2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With tri-tert-butyl phosphine; palladium diacetate; sodium t-butanolate In toluene at 80 - 120℃; for 4h; Inert atmosphere; 3 A 2L three-necked flask equipped with magnetic stirring. After nitrogen replacement, sodium tert-butoxide (14.4g, 0.15mol), dinaphthylamine (26.9g, 0.1mol) and 400ml of toluene were added in sequence. After replacing with nitrogen again, (0.4 g, 2 mmol) tri-tert-butyl phosphine and (0.23 g, 1 mmol) palladium acetate were sequentially added. After the addition, heat to 85°C. The solution consisting of (56.7 g, 0.1 mol) I-19-1 and 100 ml of toluene was added dropwise, and the temperature was controlled at 80-120° C. to react for 4 hours, and the reaction was completed. Adjust to neutral, separate the organic phase, extract, dry, column chromatography, spin-dry the solvent to obtain 56.0 g of light yellow solid, with a yield of about 70%.
  • 76
  • [ 532-18-3 ]
  • 4-(furan-2-ylmethylene)-3-(trifluoromethyl)isoxazol-5(4H)-one [ No CAS ]
  • C29H19F3N2O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
32% With 1,1,1,3',3',3'-hexafluoro-propanol In dichloromethane at 23℃; for 24h;
  • 77
  • [ 108-86-1 ]
  • [ 532-18-3 ]
  • N,N-di(2-naphthyl)aniline [ No CAS ]
YieldReaction ConditionsOperation in experiment
89% With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In toluene at 120℃; for 5h; Inert atmosphere; 1 The raw material 3 (59.0mmol),Raw material 4 (70.9mmol) was dissolved in 150mL of toluene and the air was exchanged 3 times,Add palladium catalyst (0.59mmol) under nitrogen atmosphere,The temperature of tri-tert-butyl phosphine (2.95 mmol) and sodium tert-butoxide (118 mmol) was raised to 120° C., stirred for 5 hours, and the reaction was completed. Then the mixture was extracted with dichloromethane and water; then the extracted organic layer was dried with anhydrous sodium sulfate, and the solvent was removed using a rotary evaporator; DCM and absolute ethanol (volume ratio 1:4) were precipitated to obtain Intermediate 2 (18.2 g, the yield is 89.0%, MW: 345.41).
  • 78
  • [ 532-18-3 ]
  • C30H19ClN2O2 [ No CAS ]
  • C50H33N3O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With tri-tert-butyl phosphine; palladium diacetate; sodium t-butanolate In toluene at 80 - 120℃; for 4h; Inert atmosphere; 31 Take a 2L three-necked flask with magnetic stirring. After nitrogen replacement, add sodium tert-butoxide (14.4g, 0.15mol), dinaphthylamine (26.9g, 0.1mol) and 400ml of toluene. After replacing with nitrogen again, (0.4 g, 2 mmol) tri-tert-butyl phosphine and (0.23 g, 1 mmol) palladium acetate were sequentially added. After the addition, heat to 85°C. A solution consisting of (47.4g, 0.1mol) I-23-1 and 100ml of toluene was started to be added dropwise, and the temperature was controlled at 80-120°C for 4 hours to complete the reaction. Adjust to neutral, separate the organic phase, extract, dry, column chromatography, and spin-dry the solvent to obtain 53.0 g of light yellow solid with a yield of about 75%.
  • 79
  • [ 608-21-9 ]
  • [ 532-18-3 ]
  • C26H17Br2N [ No CAS ]
YieldReaction ConditionsOperation in experiment
60% With bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate; XPhos; In toluene; at 80℃; for 3h;Inert atmosphere; 1,2,3-tribrorobenzene (3.15g, 10.0mmol) and bis(naphthalen-2-yl)amine (2.69g, 10.0mmol), t-BuONa (1.92g, 20.0mmol), toluene (45mL) Was put in. Nitrogen was blown, and Pd2(dba)3 (0.183g, 0.200mmol) and Xphos (0.19g, 0.400mmol) were added, followed by stirring at 80 C. for 5 hours, and then cooled to room temperature. After adding dichloromethane and purified water, the layers were separated. An organic layer was obtained, dried over MgSO4, and filtered. After the filtrate was concentrated, compound 5-1 (3.42g, 68%) was obtained by column chromatography (dichloromethane/heptane).
  • 80
  • [ 532-18-3 ]
  • C41H29BrN2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate; XPhos / toluene / 3 h / 80 °C / Inert atmosphere 2: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / toluene / 5 h / 80 °C / Inert atmosphere
  • 81
  • [ 532-18-3 ]
  • C41H27BN2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate; XPhos / toluene / 3 h / 80 °C / Inert atmosphere 2.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / toluene / 5 h / 80 °C / Inert atmosphere 3.1: n-butyllithium / hexane / 3 h / -20 - 20 °C / Inert atmosphere 3.2: 0.5 h / 0 - 20 °C / Inert atmosphere 3.3: alkylamine derivative / 2 h / 0 - 70 °C / Inert atmosphere
  • 82
  • [ 532-18-3 ]
  • C43H28ClNO4S [ No CAS ]
  • C63H42N2O4S [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% With tri-tert-butyl phosphine; palladium diacetate; sodium t-butanolate In toluene at 85 - 120℃; for 6h; Inert atmosphere; 14 A 2L three-necked flask equipped with magnetic stirring. After nitrogen replacement, add sodium tert-butoxide (28.8g, 0.3mol), dinaphthylamine (26.9g, 0.1mol) and 400ml of toluene in sequence.After replacing with nitrogen again, (0.4 g, 2 mmol) tri-tert-butyl phosphine and (0.25 g, 1 mmol) palladium acetate were sequentially added. After the addition, heat to 85°C.Start dropping a solution consisting of (68.9g, 0.1mol) I-70-1 and 100ml of toluene,Heat to reflux (110-120°C) and react for 6 hours, and the reaction is complete. Adjusted to neutral,Separate the organic phase, extract, dry, column chromatography, spin-dry the solvent,73.8 g of light yellow solid I-70 was obtained with a yield of 80%.
  • 83
  • [ 532-18-3 ]
  • C16H7BrO4S [ No CAS ]
  • C36H21NO4S [ No CAS ]
YieldReaction ConditionsOperation in experiment
65.4% With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In toluene at 110 - 120℃; for 4h; Inert atmosphere; 3 Example 3 Synthesis of Compound I-8 The synthetic route is as follows: Take a 2L three-necked flask with magnetic stirring, add sodium tert-butoxide (28.8g, 0.3mol), dinaphthylamine (26.9g, 0.1mol) and 400ml of toluene after nitrogen replacement. After replacing with nitrogen again, (0.4 g, 2 mmol) tri-tert-butyl phosphine and (0.92 g, 1 mmol) tribenzylidene acetone dipalladium were sequentially added. After the addition, heat to 85°C. A solution consisting of (37.5g, 0.1mol) M3 and 100ml of toluene was added dropwise, heated to reflux (110-120°C) for 4 hours, and the reaction was completed. Adjust to neutral, separate the organic phase, extract, dry, column chromatography, and spin-dry the solvent to obtain 36.8 g of pale yellow solid I-8 with a yield of 65.4%.
  • 84
  • [ 532-18-3 ]
  • [ 814-68-6 ]
  • N,N-di-2-naphthylacrylamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
49% With <i>N</i>,<i>N</i>-dimethyl-aniline In dichloromethane at 10 - 20℃; for 24h; Inert atmosphere; 8.1 (1) Synthesis of N,N-di-2-naphthyl-acrylamide A 100 mL four-necked flask substituted with nitrogen was charged with di-2-naphthylamine (5.00 g, 18.6 mmol), N, N-dimethylaniline (4.50 g, 37.1 mmol), and 50 mL of super-dehydrated dichloromethane. The reaction solution was cooled to 10 ° C. or lower in an ice bath, chloride (2.52 g, 27.8 mmol) was slowly added dropwise, and the mixture was stirred for 30 minutes. Then, the reaction solution was heated to room temperature, and the reaction was carried out for 24 hours. After completion of the reaction, the reaction solution was washed with 1N aqueous hydrochloric acid solution, saturated aqueous sodium hydrogen carbonate solution and brine. The organic layer was dehydrated with magnesium sulfate, and then the filtrate was evaporated with an evaporator. Purification by column chromatography (ethyl acetate / hexane = 1/10) gave N, N-di-2-naphthyl-acrylamide (2.94 g, 49% yield).
  • 85
  • [ 532-18-3 ]
  • C26H17NS [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sulfur; iodine / 1,2-dichloro-benzene / 4 h / 160 °C / Inert atmosphere; Schlenk technique 2: palladium diacetate; tri-tert-butyl phosphine; potassium <i>tert</i>-butylate / toluene / 12 h / 110 °C / Inert atmosphere; Schlenk technique
  • 86
  • [ 532-18-3 ]
  • C25H16N2O2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: sulfur; iodine / 1,2-dichloro-benzene / 4 h / 160 °C / Inert atmosphere; Schlenk technique 2: palladium diacetate; tri-tert-butyl phosphine; potassium <i>tert</i>-butylate / toluene / 12 h / 110 °C / Inert atmosphere; Schlenk technique 3: dihydrogen peroxide; acetic acid / dichloromethane; water / 24 h / Reflux
  • 87
  • [ 532-18-3 ]
  • C26H17NO2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: sulfur; iodine / 1,2-dichloro-benzene / 4 h / 160 °C / Inert atmosphere; Schlenk technique 2: palladium diacetate; tri-tert-butyl phosphine; potassium <i>tert</i>-butylate / toluene / 12 h / 110 °C / Inert atmosphere; Schlenk technique 3: dihydrogen peroxide; acetic acid / dichloromethane; water / 24 h / Reflux
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