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Chemical Structure| 785051-54-9
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Product Details of [ 785051-54-9 ]

CAS No. :785051-54-9 MDL No. :MFCD16294549
Formula : C24H24BNO2 Boiling Point : -
Linear Structure Formula :- InChI Key :AHDSYMVAUJZCOP-UHFFFAOYSA-N
M.W : 369.26 Pubchem ID :11850073
Synonyms :

Calculated chemistry of [ 785051-54-9 ]

Physicochemical Properties

Num. heavy atoms : 28
Num. arom. heavy atoms : 19
Fraction Csp3 : 0.25
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 117.26
TPSA : 23.39 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : Yes
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -4.31 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 5.98
Log Po/w (WLOGP) : 5.08
Log Po/w (MLOGP) : 3.92
Log Po/w (SILICOS-IT) : 3.97
Consensus Log Po/w : 3.79

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -6.27
Solubility : 0.0002 mg/ml ; 0.000000541 mol/l
Class : Poorly soluble
Log S (Ali) : -6.25
Solubility : 0.000209 mg/ml ; 0.000000565 mol/l
Class : Poorly soluble
Log S (SILICOS-IT) : -8.2
Solubility : 0.00000235 mg/ml ; 0.0000000064 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 3.22

Safety of [ 785051-54-9 ]

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 [ 785051-54-9 ]

* 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.

  • Upstream synthesis route of [ 785051-54-9 ]
  • Downstream synthetic route of [ 785051-54-9 ]

[ 785051-54-9 ] Synthesis Path-Upstream   1~19

  • 1
  • [ 57102-42-8 ]
  • [ 73183-34-3 ]
  • [ 785051-54-9 ]
YieldReaction ConditionsOperation in experiment
87% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In 1,4-dioxane at 85℃; for 48 h; To a 100 ml round bottom flask was added 1 g of 4-bromobenzoxazole (3.1 mmol), 0.79 g of bis(pinacol) diboron(3.1 mmol), 30 ml of 1,4-dioxane, 0.4 g of potassium acetate ( 4 mmol), 0.13 g of [1,1'-bis(diphenylphosphino)ferrocene]palladium dichloride dichloromethane complex (0.16 mmol), and reacted at 85 ° C for 48 hours.After cooling to room temperature, thereaction was quenched by theaddition of 200 mL(3M) aqueous hydrochloric acid,The organic layers were combined, washed with aq.After evaporating the solvent, it was purified by column chromatographyusing dichloromethane: petroleum ether = 1:2 (volume ratio) as a eluting solvent to afford 1 g of product E1, yield 87percent.
86%
Stage #1: With potassium acetate In dimethyl sulfoxide at 60℃; for 0.25 h;
Stage #2: With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In dichloromethane; dimethyl sulfoxide at 80℃; for 6 h;
Under nitrogen flow, the target compound 21 (4.50 g), bis(pinacolate)diboron (4.61 g), potassium acetate (4.61 g), and dimethylsulfoxide (75 ml) were stirred while heating to 60°C for 15 min, and [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane complex (0.343 g) was added thereto. The resulting mixture was stirred while heating to 80°C for 6 hr and then allowed to cool to room temperature. To the reaction solution, water (250 ml) and toluene (500 ml) were added, and the resulting mixture was stirred. After the water layer was reextracted twice with toluene, the organic layers were mixed. Further, magnesium sulfate and active clay were added thereto. The magnesium sulfate and active clay were removed by filtration, and the toluene was evaporated under reduced pressure. The precipitated crystal was washed with cold methanol and dried under reduced pressure to obtain a target compound 22 (4.46 g, yield: 86percent) as a white crystal.
85.1% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxaneInert atmosphere; Reflux General procedure: A solution of haloarene (1.0 mmol ratio), bis(pinacolate)diboron (1.2 mmol ratio), KOAc (1.5 mmol ratio), andPdCl2(dppf) (0.02 mmol ratio) in dry 1,4-dioxane (20 ml)was refluxed for overnight under N2. After being cooledto room temperature, the mixture was poured into H2Oand then extracted with dichloromethane. The combinedorganic layer was washed with brine and dried over magnesiumsulfate. The solvent was removed in vacuo andcrude product was purified by chromatography (SiO2) elutingwith a mixture of DCM and n-hexane to afford the pureproducts. 2.2.3. 9-(4-(4,4,5,5,-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-9H-carbazole (2); 9-(4-Bromophenyl)-9H-carbazole (5.5 g, 17.19 mmol),bis(pinacolate)diboron (5.24 g, 20.63 mmol), KOAc (2.63 g,25.76 mmol), and PdCl2(dppf) (0.15 g, 0.02 mmol) wereused to yield compound 2 (5.36 g, 85.1percent) as a white solid:m.p. = 170 °C
81% With potassium acetate In 1,4-dioxane at 80℃; for 67 h; Inert atmosphere 0132] 9-(4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)phenyl)-9H- carbazole (5). Compound 5 was prepared as follows: a mixture of 4 (11.64 g, 36.12 mmol), bis(pinacolato)diboron (19.26 g, 75.85 mmol), [l ,l '-bis(diphenylphosphino)- ferrocene]dichloropalladium(II) (1.59 g, 2.17 mmol), potassium acetate (10.64, 108.4 mmol) and anhydrous 1 ,4-dioxane (200 mL) was degassed with argon for about 2 h while stirring. The stirring reaction mixture was then maintained under argon at about 80 °C for about 67 h. Upon confirming consumption of the starting material by TLC (Si02, hexanes), the mixture was cooled to RT, filtered through a short silica gel plug and the filtrant washed copiously with EtOAc (ca. 400 mL). The organics were then washed with sat. NaHCC>3, H20 and brine, dried over MgS04, filtered and concentrated in vacuo. Purification of the crude product via flash chromatography (Si02, 7:3 to 1 : 1 hexanes- dichloromethane) provided compound 5 (10.8 g, 81 percent yield) as a colorless solid. (See Sun, Y.; Zhu, X.; Chen, Z.; Zhang, Y.; Cao, Y. /. Org. Chem. , 2006, 71(16), 6281-6284.)
81% With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; tris-(dibenzylideneacetone)dipalladium(0); potassium acetate In 1,4-dioxane for 24 h; Inert atmosphere; Reflux In 500 mL three-necked flask, followed by adding intermediate M9 (20g, 62.lmmol), bis (pinacolato) diboron (23.6g, 93.2mmol), CH3COOK (17.5g, 178.2mmol), 1, 4- dioxane, 300 mL, and S-phos (5.35g, 13.04mmol), N2 replaced three times, was added Pd2 (dba) 3 (3.98g, 4.35mmol) and heated to reflux. After 24h the reaction was stopped.It cooled to room temperature, filtered, and the filtrate was collected, concentrated, and purified by column chromatography (dichloromethane: n-hexane = 0-1 as the mobile phase), to receive an off-white solid 18.5g (81percent),
80% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 20 - 80℃; for 21 h; Inert atmosphere A Schlenk flask was charged with compound 1 (600 mg, 1.87 mmol), then bis(pinacolato)diboron (522 mg, 2.06 mmol), PdCl2DPPF (113 mg, 0.14 mmol), KOAc (550 mg, 5.61 mmol) and dry 1, 4-dioxane (15 mL) were added to the flask under argon. The mixture was preactivated for 1 h under room temperature followed by immersing in an oil bath at 80 °C with stirring for about 20 h until the starting material had completely disappeared as judged by TLC. The solvent was evaporated under reduced pressure and purified by column chromatography (Hexanes/EtOAc=200/1) to give compound 2 (546.4 mg, 1.48 mmol, 80percent) as pale yellow solid; mp: 173-174 °C; 1H NMR (400 MHz, CDCl3): δ 8.14 (d, J=7.7 Hz, 2H), 8.05 (d, J=8.2 Hz, 2H), 7.59 (d, J=8.2 Hz, 2H), 7.48-7.36 (m, 4H), 7.33-7.25 (m, 2H), 1.40 (s, 12H).
75% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In N,N-dimethyl-formamide at 100℃; for 6 h; Inert atmosphere 9-(4-bromophenyl)-9H-carbazole (3.2 g, 10 mmol),bis(pinacolato)diboron (3.3 g, 13 mmol), PdCl2(dppf)CH2Cl2(244.8 mg, 0.3 mmol) and KOAc (3.0 g, 30 mmol) were dissolved inN,N-dimethylformamide (50 mL), and were heated to 100 °C underthe nitrogen atmosphere for 6 h. The mixture was washed withgreat deal of distilled water after cooling to the room temperature.The organic phase was dried with anhydrous sodium sulfate,filtered and concentrated in vacuum. The crude product was subjectedto silica gel column chromatography using a 5:1 (V/V)mixture of petroleum ether and dichloromethane as the eluent toafford the white solid (yield 75percent). 1H NMR (600 MHz, CDCl3, δ): 8.14(d, 2H, J = 7.8 Hz), 8.06-8.03 (m, 2H), 7.61-7.57 (m, 2H), 7.45-7.43(m, 2H), 7.40 (d, 2H, J = 8.3 Hz), 7.28 (d, 2H, J = 8.0 Hz), 1.40 (s, 12H).Anal. Calcd for C24H24O2NB: C, 78.26; H, 6.52; N, 3.80. Found: C,78.92; H, 6.306; N, 3.74.
72% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 130℃; for 12 h; Inert atmosphere Under a nitrogen flow 9- (4-bromophenyl) -9H-carbazole (30g, 0.093mol), 4,4,4 ', 4', 5,5,5 ', 5'-octamethyl-2,2'-bi ( 1,3,2-dioxaborolane) (47.2g, 0.186 mol), Pd (dppf) Cl2 (3.4g, 0.004 mol), KOAc (27.4g, 0.279 mol), and A mixture of 1,4-dioxane (600ml) and stirred for 12 hours at 130 . After the reaction was terminated, extracted with ethyl acetate, and the removal of water with MgSO4, and purified by column chromatography [Hexane: Dichloromethane (MC) = 10: 1 (v / v)] purified intermediate 1-A [9- (by a 4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) -9H-carbazole] to obtain a (24.75 g, 72percent yield).
71.5% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In toluene for 10 h; Reflux 9-(4- bromophenyl)-9H-carbazole 24 g (34mmol),the bis pinacolrato diboron 20.4 g (41 mmol), the palladium(II)chloridation-1,1'-bis(diphenyl phosphino)ferrocene 1.4 g (1 mmol), potassiumacetate 6.7 g (68mmol), toluene 240 ml is put in dried 500mL reactor and it mixes reflux for 10 hours. After solid is filtered after thecompletion of reaction the filtrate is reduced pressureand it concentrates. It separated according to the methylene chloride and heptane into the column chromatography and 003c3-c003e 20.5 g was obtained. (yield71.5percent)
70% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 90℃; for 24 h; Inert atmosphere Synthesis of M6: M6 was prepared by Suzuki coupling.In a 100 mL round bottom flask,Will M5 (5mmol, 1.61g),Bornazolium diborate (10 mmol, 2.54 g),Potassium acetate (15 mmol, 1.47 g),[1,1'-bis(diphenylphosphino)ferrocene]palladium dichloride (0.1 mmol, 73 mg) was dissolved in 60 mL of dioxane.The mixture was stirred under reflux at 90 ° C for 24 hours under nitrogen.After the reaction is over,Extracted with dichloromethane,Concentrate the extract by rotary evaporation,Column chromatography separation (petroleum ether: dichloromethane = 4:1, volume ratio) gave a white solid(1.29 g, yield: 70percent).
69.8% at 80℃; for 8 h; Synthesis of 9- (4-bromophenyl) -9H-carbazole Reference is made to the method described in Journal of Materials Science 2004, 14, 895-900.A solution of 0.99 g (3.1 mmol) of 9- (4-bromophenyl) -9H-carbazole, 0.87 g (3.4 mmol) of pinacol bisborate, 71 mg (87 mol) of PdCl2(Dppf), 0.90 g (9.2 mmol) of potassium acetate, argon was purged three times, 18 mL of dimethylsulfoxide (DMSO) was added, and the mixture was again purged with air and heated in an oil bath to 80 ° C.After the end of the reaction, the reaction product was poured into a large number of distilled water, ether extraction, dry spinning, with VPetroleum ether: VtwoChloromethane= 5: 1 for the eluent, 200-300 mesh silica gel as the stationary phase, column separation of 9 - (4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolane -2-yl) phenyl) -9H-carbazole as a white solid. The yield was 69.8percent.
61.2% With palladium bis[bis(diphenylphosphino)ferrocene] dichloride; potassium acetate In 1,4-dioxane at 80℃; for 24 h; Inert atmosphere Under a nitrogen atmosphere, A1 (6.4 g, 20.0 mmol), boronic acid pinacol ester (5.59 g, 22.0 mmol), PdCl2(Dppf)2(0.4 g, 0.6 mmol), potassium acetate (5.9 g, 60.0 mmol) and 120 ml of anhydrous dioxane were added and heated to 80 ° C with stirring for 24 hours.After completion of the reaction, the reaction solution was allowed to cool to room temperature and then poured into an appropriate amount of water and extracted with methylene chloride. The resulting organic phase was dried over anhydrous magnesium sulfate and the organic solvent was removed by rotary evaporator. The initial product was purified by chromatography And the eluent was petroleum ether / dichloromethane to give 4.5 g of a pale yellow solid (yield: 61.2percent).
55% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 20 - 80℃; for 47 h; Inert atmosphere Example 1.7.11
9-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-9H-carbazole (Compound 11)
A mixture of 9-(4-bromophenyl)-9H-carbazole (7.39 g, 22.93 mmol), bis(pinacolato)diboron (6.40 g, 25.22 mmol), [1,1'-bis(diphenyl-phosphino)ferrocene]-dichloropalladium(II) (0.836 g, 1.15 mmol), potassium acetate (6.75 g, 68.78 mmol), and anhydrous 1,4-dioxane (125.00 mL) was degassed with bubbling argon for 1 hour at room temperature.
The reaction was then heated to 80° C. and was stirred over two nights (46 hours), maintaining an argon atmosphere.
Consumption of the starting material was confirmed by thin-layer chromatography and the reaction was cooled to room temperature.
The product was then extracted with ethyl acetate, dried, and purified by silica gel column chromatography with dichloromethane in hexanes as the eluent.
The product fractions were then dried to yield Compound 11 (4.63 g, 55percent).

Reference: [1] Chemical Communications, 2012, vol. 48, # 71, p. 8970 - 8972
[2] Patent: CN108191739, 2018, A, . Location in patent: Paragraph 0087; 0088; 0089
[3] Patent: EP1820801, 2007, A1, . Location in patent: Page/Page column 88
[4] Organic Electronics: physics, materials, applications, 2014, vol. 15, # 7, p. 1413 - 1421
[5] Patent: WO2012/37269, 2012, A1, . Location in patent: Page/Page column 45-46
[6] Patent: CN103951621, 2016, B, . Location in patent: Paragraph 0081; 0082; 0083; 0086; 0087
[7] Tetrahedron, 2016, vol. 72, # 35, p. 5495 - 5501
[8] Dyes and Pigments, 2017, vol. 146, p. 316 - 322
[9] Patent: KR2015/118847, 2015, A, . Location in patent: Paragraph 0073; 0075-0078
[10] Patent: KR2016/26661, 2016, A, . Location in patent: Paragraph 0506-0511
[11] Patent: CN108191847, 2018, A, . Location in patent: Paragraph 0063-0064
[12] Patent: CN102977143, 2016, B, . Location in patent: Paragraph 0133-0135
[13] RSC Advances, 2015, vol. 5, # 22, p. 17030 - 17033
[14] Patent: CN103951705, 2016, B, . Location in patent: Paragraph 0048-0050
[15] Patent: US9425408, 2016, B2, . Location in patent: Page/Page column 34-35
[16] Chemistry Letters, 2007, vol. 36, # 9, p. 1156 - 1157
[17] Patent: KR2016/51210, 2016, A, . Location in patent: Paragraph 0122; 0123; 0124
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  • [ 785051-54-9 ]
YieldReaction ConditionsOperation in experiment
80%
Stage #1: With n-butyllithium In tetrahydrofuran at -78℃; Inert atmosphere
Stage #2: at 20℃; Inert atmosphere
Under nitrogen, 9- (4-bromophenyl) carbazole (3g, 9.32mmol) was dissolved in dry tetrahydrofuran (120mL) And cooled to about -78 ° C, was slowly added dropwise a solution of n-butyllithium (1.6mL, 2.5M, 4.84mmol) via syringe, and the Temperature for 15 to 20 minutes, and then added isopropoxy pinacol boronate (2.6mL, 13.04mmol); slow reaction system Slow return to room temperature and under N 2 atmosphere overnight. After completion of the reaction was added 1 ~ 2mL of ethanol to terminate the reaction, and evaporate After the solvent was distilled off, and distilled water was added methylene chloride. The organic layer was dried over anhydrous magnesium sulfate, filtered, and evaporated under reduced pressure After the solvent was separated by a silica gel column, eluted with dichloromethane and petroleum ether to give a white solid, a yield of 80percent (2.75g).
71%
Stage #1: With n-butyllithium In tetrahydrofuran at -78℃; for 2 h; Inert atmosphere
Stage #2: at -78 - 20℃; for 25 h; Inert atmosphere
In an argon atmosphere,9-(4-bromophenyl)-9H-carbazole (12.4 g, 38.4 mmol)Dissolved in 180 mL refined THF2.4 mL of n-butyllithium (2.4 mL) was gradually added dropwise at -78°C.After reacting for 2 hours, 12.5 g of 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane was added.The reaction was continued at -78 °C for 1 hour.Then warmed to room temperature for 24 hours;The reaction mixture was poured into water, extracted with ethyl acetate, the organic layer was completely washed with brine, and dried over anhydrous magnesium sulfate;After the solution was concentrated, a pale yellow viscous crude product was obtained, which was purified by silica gel column chromatography. The mixture of petroleum ether and dichloromethane (6/1, v/v) was used as eluent to obtain a white solid with a yield of 71percent.
66.7%
Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -70 - -40℃; for 1 h; Inert atmosphere
Stage #2: at -70 - 20℃;
37.8 g (117 mmol) of the intermediate product (F) was dissolved in 378 ml of tetrahydrofuran, 100.5 ml (lδlmmol) of 1.6M n-butyl lithium hexane solution was added at -70 ° C under argon atmoshhere, and then the resulting solution was agitated at -70 ° C to -40 C for 1 hour. The reaction fluid was cooled to -70 ° C and 47.9 ml (235 mmol) of isopropyl tetramethyl dioxaboloane was added in a dropwise fashion. After the resulting solution was agitated at -70 °C for 1 hour, the temperature increased to a room temperature and agiting was performed for 6 hours. 200 ml of water was added to the resulting solution and then agitated for 20 minutes.<159> After separating the reaction fluid into two layers, an organic layer was washed with a saturated sodium chloride aqueous solution and dried with anhydrous sodium sulfate.<i60> The organic solvent was distillated and removed under reduced pressure, and then the residue was recrystallized with toluene. The obtained crystal was separated by filtration and washed with toluene to obtain 28.9 g (yield- 66.7 percent) of intermediate product (G).
66.7%
Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -70 - 40℃; for 1 h; Inert atmosphere
Stage #2: at -70 - 20℃; for 7 h;
Step 2: Synthesis of Intermediate (B)37.8 g (117 mmol) of the intermediate (A) was dissolved in 378 ml of tetrahydrofuran, then 100.5 ml (161 mmol) of n-butyl lithium hexane solution (1.6M) was added thereto under an argon atmosphere at -70° C. The obtained solution was agitated at -70° C. to 40° C. for 1 hour. The reaction fluid was frozen to -70° C., and 47.9 ml (235 mmol) of isopropyl tetramethyl dioxaborolane was slowly added thereto in a dropwise fashion. The obtained solution was agitated at -70° C. for 1 hour and heated to room temperature, and then agitated for 6 hours. To the obtained reaction solution, 200 ml of water was added and agitated for 20 minutes.The reaction solution was separated into two liquid layers, and an organic layer thereof was dried with anhydrous sodium sulfate. After the organic solvent was removed under a reduced pressure, the obtained residue was purified with silica gel column chromatography to provide 28.9 g of the intermediate (B) (yield 66.7percent).
54%
Stage #1: With n-butyllithium In tetrahydrofuran at -78℃; for 0.5 h; Inert atmosphere
Stage #2: at 20℃; for 12 h; Inert atmosphere
n-Butyllithium (26 ml, 41.59 mmol) was added to a solution of 9-(4-bromophenyl)-9H-carbazole (6.7 g, 20.79 mmol) in anhydrous tetrahydrofuran (70 ml) at −78°C under nitrogen atmosphere. The mixture was stirred for 30 min at the same temperature. And then, 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (21.2 ml, 103.97 mmol) was added dropwise to the reaction mixture and stirred for 12h at room temperature. The reaction mixture was poured into water and extracted with chloroform. The organic layer was separated, dried over anhydrous magnesium sulfate, and evaporated under reduced pressure. The crude product was purified by silica gel column chromatography using toluene eluent to afford ( 2) a white powder, yield 54percent. 1H NMR (CDCl3, 400MHz) 8.17–7.15 (d, J=8Hz, 2H), 8.10–8.08 (d, J=8Hz, 2H), 7.64–7.62 (d, J=8.4Hz, 2H), 7.49–7.47 (d, J=8Hz, 2H), 7.45–7.41 (t, J=6.8Hz, 2H), 7.33–7.29 (t, J=6.8Hz, 2H), 1.43 (s, 12H) ppm.

Reference: [1] Chinese Journal of Chemistry, 2015, vol. 33, # 8, p. 873 - 880
[2] Journal of Organic Chemistry, 2006, vol. 71, # 16, p. 6281 - 6284
[3] Chemistry Letters, 2008, vol. 37, # 9, p. 986 - 987
[4] Patent: CN105461717, 2016, A, . Location in patent: Paragraph 0087-0089
[5] Patent: CN107954921, 2018, A, . Location in patent: Paragraph 0085; 0086
[6] Patent: WO2010/24572, 2010, A2, . Location in patent: Page/Page column 27-28
[7] Patent: US2012/280221, 2012, A1, . Location in patent: Page/Page column 22
[8] Dyes and Pigments, 2014, vol. 111, p. 116 - 123
[9] Journal of Materials Chemistry C, 2013, vol. 1, # 24, p. 3871 - 3878
[10] Chemistry Letters, 2007, vol. 36, # 9, p. 1156 - 1157
[11] Chemistry Letters, 2007, vol. 36, # 9, p. 1156 - 1157
[12] European Journal of Organic Chemistry, 2012, # 27, p. 5263 - 5274
[13] Dyes and Pigments, 2013, vol. 99, # 1, p. 41 - 51
  • 3
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  • [ 73183-34-3 ]
  • [ 785051-54-9 ]
YieldReaction ConditionsOperation in experiment
71% With bis[1,2-bis(diphenylphosphino)ferrocene]-palladium(0); potassium acetate In N,N-dimethyl-formamide at 150℃; for 46 h; Inert atmosphere In a nitrogen atmosphere, I-1 (150 g, 540 mmol)Was dissolved in 1,600 mL of dimethylforamide (DMF)Bis (pinacolato) diboron (165 g, 648 mmol) was added thereto,And 1,1-bis (diphenylphosphine) ferrocene) dichloropalladium (II) (4.41 g, 5.4 mmol)And potassium acetate (132 g, 1350 mmol)And the mixture was refluxed by heating at 150 ° C for 46 hours.After completion of the reaction, water was added to the reaction solution, the mixture was filtered, and then dried in a vacuum oven.The residue thus obtained was separated and purified by flash column chromatography to obtain Compound I-2 (142 g, 71percent).
Reference: [1] Patent: KR2015/24669, 2015, A, . Location in patent: Paragraph 0116-0118
[2] Patent: KR2015/84657, 2015, A, . Location in patent: Paragraph 1170
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Reference: [1] Organic Letters, 2016, vol. 18, # 12, p. 2966 - 2969
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Reference: [1] Patent: CN106632269, 2017, A, . Location in patent: Paragraph 0040; 0044; 0045; 0046
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  • [ 1394130-73-4 ]
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  • [ 785051-54-9 ]
Reference: [1] Organic Letters, 2012, vol. 14, # 17, p. 4560 - 4563
  • 7
  • [ 419536-33-7 ]
  • [ 76-09-5 ]
  • [ 785051-54-9 ]
Reference: [1] Journal of Materials Chemistry C, 2018, vol. 6, # 32, p. 8733 - 8737
  • 8
  • [ 57102-42-8 ]
  • [ 76347-13-2 ]
  • [ 785051-54-9 ]
Reference: [1] Chinese Journal of Chemistry, 2017, vol. 35, # 10, p. 1559 - 1568
  • 9
  • [ 589-87-7 ]
  • [ 785051-54-9 ]
Reference: [1] Chemistry Letters, 2007, vol. 36, # 9, p. 1156 - 1157
[2] Dyes and Pigments, 2013, vol. 99, # 1, p. 41 - 51
[3] Tetrahedron, 2016, vol. 72, # 35, p. 5495 - 5501
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