[ CAS No. 1205748-61-3 ] {[proInfo.proName]}

Name: 1205748-61-3|2,4-Di([1,1'-biphenyl]-3-yl)-6-chloro-1,3,5-triazine|97%
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Quality Control of [ 1205748-61-3 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 1205748-61-3 ]

SDS Specification

Alternatived Products of [ 1205748-61-3 ]

Product Details of [ 1205748-61-3 ]

CAS No. :	1205748-61-3	MDL No. :	MFCD30536777
Formula :	C₂₇H₁₈ClN₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	SVNMSEVGOAHNKQ-UHFFFAOYSA-N
M.W :	419.91	Pubchem ID :	58299118
Synonyms :

Calculated chemistry of [ 1205748-61-3 ] Expand+

Physicochemical Properties

Num. heavy atoms :	31
Num. arom. heavy atoms :	30
Fraction Csp3 :	0.0
Num. rotatable bonds :	4
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	126.58
TPSA :	38.67 Å²

Pharmacokinetics

GI absorption :	Low
BBB permeant :	No
P-gp substrate :	Yes
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-3.53 cm/s

Lipophilicity

Log Po/w (iLOGP) :	4.64
Log Po/w (XLOGP3) :	7.51
Log Po/w (WLOGP) :	7.19
Log Po/w (MLOGP) :	5.22
Log Po/w (SILICOS-IT) :	7.09
Consensus Log Po/w :	6.33

Druglikeness

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

Water Solubility

Log S (ESOL) :	-7.63
Solubility :	0.00000992 mg/ml ; 0.0000000236 mol/l
Class :	Poorly soluble
Log S (Ali) :	-8.16
Solubility :	0.00000293 mg/ml ; 0.000000007 mol/l
Class :	Poorly soluble
Log S (SILICOS-IT) :	-11.87
Solubility :	0.0000000006 mg/ml ; 0.0 mol/l
Class :	Insoluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	2.0
Synthetic accessibility :	3.01

Safety of [ 1205748-61-3 ]

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 [ 1205748-61-3 ]

* 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.

Upstream synthesis route of [ 1205748-61-3 ]
Downstream synthetic route of [ 1205748-61-3 ]

[ 1205748-61-3 ] Synthesis Path-Upstream 1~3

1
[ 108-77-0 ]
[ 2113-57-7 ]
[ 1205748-61-3 ]

Yield	Reaction Conditions	Operation in experiment
84%	Stage #1: With magnesium In tetrahydrofuran for 1.5 h; Heating Stage #2: at 20℃; for 12 h;	5.2 g Magnesium (0.215 mol) was introduced in 500 ml 4-necked flask, 50 g of bromobiphenyl (214 mmol) in 200 ml THF was added dropwise. The reaction mixture was heated for 1.5 h and then subsequently cooled to room temperature. Cyanuric chloride (17.2 g, 93 mmol) in 150 ml THF was introduced to the second flask,and cooled to 0°C. Grignard reagent was added, and the mixture was stirred at room temperature for 12 h. After this, 150 ml of HCl was added to the reaction mixture, aqueous phase was extracted 3 times with dichloromethane. The combined organic phases washed with water, dried using Na2SO4 and evaporated. Then the residue was recrystallized from EtOH. The yield is 32.8 g (78 mmol, 84percent).
65%	Stage #1: With magnesium In tetrahydrofuran for 2 h; Reflux Stage #2: at 0 - 20℃; for 16 h;	In THF (20ml), was prepared 3-bromo-1,1'-biphenyl (10.73l, 64.3mmol) and Mg (4.69g, 193mmol) and then refluxed for 2 hours [1,1' biphenyl]-3-solution in THF (80ml) of the Il magnesium bromide was added dropwise at 0 to a solution of 2,4,6-trichloro-1,3,5-triazine (3.96g, 21.45mmol). The reaction mixture was slowly warmed to room temperature, and stirred for 16 hours and quenched with 10percent aqueous HCl. Extracted with DCM, washed with water, and dried with sodium sulfate (Na2SO4). Evaporation of the solvent by silica gel column chromatography using heptane / DCM as eluent (9/1 ~ 7/3, v / v), purified the crude product as a white solid of 2,4-di-([1,1'-biphenyl]-3-yl)-6-chloro-1,3,5-triazine (2.30g, 65percent)

Reference： [1] Patent: KR2016/28524, 2016, A, . Location in patent: Paragraph 0221-0223
[2] Patent: JP2016/6039, 2016, A, . Location in patent: Paragraph 0109; 0110

2
[ 2113-57-7 ]
[ 506-77-4 ]
[ 1205748-61-3 ]

Yield	Reaction Conditions	Operation in experiment
84%	Stage #1: With magnesium In tetrahydrofuran at 20℃; for 1.5 h; Stage #2: at 0 - 20℃; for 12 h;	Magnesium (0.215 mol) of 5.2 g ofInitially, 500 ml 4- nine (four-necked) Introduced into the flask, and 200 ml of THF in 50 gA solution of bromobiphenyl (214 mmol) was slowly added dropwise thereto.Heating for 1.5 hours at the boiling point of the reaction mixture, andThen allowed to cool to room temperature.The cyanogen chloride (cyanogenchloride) (17.2 g, 93 mmol) in 150 ml of THF First it introduced into a second flask and cooled to 0 . Then, the coolingIt was added dropwise a Grignard (Grignard) reagent at this temperature and the mixture was stirred at room temperature for 12 hours.After said time, and extracted three times, the aqueous phase was added to 150 ml of HCl to the reaction mixture with dichloromethane.Washing the organic phase with water, combined, dried over Na2SO4, and evaporated.The residue was recrystallized from EtOH. The yield was 32.8 g (78 mmol, 84percent).

Reference： [1] Patent: KR2015/93836, 2015, A, . Location in patent: Paragraph 0217-0219

3
[ 108-77-0 ]
[ 103068-18-4 ]
[ 1205748-61-3 ]

Yield	Reaction Conditions	Operation in experiment
89%	at 0 - 20℃; Inert atmosphere	General procedure: 295g (1.6mol, 1.0eq) of 2,4,6-trichloro-1 ,3,5-triazine [108-77-0] 1 are solved in 800ml dried THF in a four-necked flask under an inert atmosphere. The solution is cooled with an ice bath to about 0°C and 800ml (1.6mol, 1.0eq) of a 2mol/l phenylmagnesiumchloride solution are added slowly to maintain the temperature below 10°C. Then, the mixture is stirred at room temperature overnight and after the reaction had finished, 800ml of toluene and 1.2L of HCI 2percent are added. The organic phase is separated, extracted three times with water and dried over sodium sulfate. The solvent is evaporated under reduced pressure until the product precipitates. After washing the solid with ethanol, 242g (1.1mol, 67percent) of the desired product 3a are obtained. Other examples are obtained analogously:
55%	at 0℃;	100.0 g (542.3 mmol) of cyanuric chloride and 700 mL of anhydrous THF were put in a 2 L flask, 361.4 mL of 3-Biphenylmagnesium bromide (3 M) was added thereto, and the mixture was slowly added thereto in a dropwise fashion at 0° C. When a reaction was complete, water was poured into the reaction solution, the mixture was stirred for 30 minutes, and an organic layer therefrom was separated, concentrated after removing moisture by using magnesium sulfate, and purified with methanol and hexane to obtain white solid Intermediate 5-1 (122.9 g, yield of 55percent). (0188) calcd. C27H18ClN3: C, 77.23; H, 4.32; Cl, 8.44; N, 10.01; found: C, 77.25; H, 4.31; Cl, 8.44; N, 10.00.

Reference： [1] Patent: WO2017/16630, 2017, A1, . Location in patent: Page/Page column 50; 51
[2] Patent: US2017/317293, 2017, A1, . Location in patent: Paragraph 0185-0188

[ 1205748-61-3 ] Synthesis Path-Downstream 1~28

1
[ 1255519-88-0 ]
[ 1205748-61-3 ]
[ 1383614-46-7 ]

Yield	Reaction Conditions	Operation in experiment
59%	With potassium phosphate;tris-(dibenzylideneacetone)dipalladium(0); tricyclohexylphosphine; In 1,4-dioxane; water; for 18h;Inert atmosphere; Reflux;	Synthesis Example 2; This example illustrates the preparation of Compound A2, shown below. A 500mL one-neck round-bottom flask equipped with a condenser and nitrogen inlet was charged with 5.55g (26.1 mmol) of potassium phosphate and 10OmL of Dl water. To this solution, 6.74g (17.44 mmol) of 2-(3-(dibenzo[b,d]thiophen-4-yl)phenyl)-4,4,5,5-tetramethyl-1 ,3,2- dioxaborolane, 6.1 g (14.53 mmol) of 2,4-di(biphenyl-3-yl)-6-chloro-1 ,3,5- triazine, and 160ml_ of 1 ,4-dioxane were added. The reaction mixture was sparged with nitrogen for 35 minutes. In the drybox, 0.4g (0.44 mmol) of tris(dibenzylideneacetone)dipalladium(0) and 0.28g (1 .15 mmol) of tricyclohexylphosphine were mixed together in 40ml_ of 1 ,4-dioxane, taken out of the box and added to the reaction mixture. Reaction mixture was sparged nitrogen for five minutes then refluxed for 18 hours. The reaction was cooled to room temperature and 1 ,4-dioxane was removed on the rotary evaporator. The residue was diluted with methylene chloride and water, then brine was added to the mixture, which was let to stand for 30 minutes. Lower level was removed along with gray solids. The aqueous layer was extracted two more times with methylene dichloride. The combined organic layers were stripped until dry. The resulting gray solid was placed on a filter paper at the bottom of a coarse fritted glass funnel and washed with 100 ml_ of water, 800 ml_ of LC grade methanol and 500 ml_ of diethyl ether. Solids were recrystallized from minimal amount of hot toluene. Yield 5.48g (59%) of desired product. Mass spectrometry and 1H NMR (CDCI2CCI2D) data were consistent with the structure of the desired product.
59%	With potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0); tricyclohexylphosphine; In 1,4-dioxane; water; for 18h;Reflux; Inert atmosphere;	A 500ml_ one-neck round-bottom flask equipped with a condenser and nitrogen inlet was charged with 5.55g (26.1 mmol) of potassium phosphate and 10OmL of Dl water. To this solution, 6.74g (17.44 mmol) of 2-(3-(dibenzo[b,d]thiophen-4-yl)phenyl)-4,4,5,5-tetramethyl-1 ,3,2- dioxaborolane, 6.1 g (14.53 mmol) of 2,4-di(biphenyl-3-yl)-6-chloro-1 ,3,5- triazine, and 160ml_ of 1 ,4-dioxane were added. The reaction mixture was sparged with nitrogen for 35 minutes. In the drybox, 0.4g (0.44 mmol) of tris(dibenzylideneacetone)dipalladium(0) and 0.28g (1 .15 mmol) of tricyclohexylphosphine were mixed together in 40ml_ of 1 ,4-dioxane, taken out of the box and added to the reaction mixture. Reaction mixture was sparged nitrogen for five minutes then refluxed for 18 hours. The reaction was cooled to room temperature and 1 ,4-dioxane was removed on the rotary evaporator. The residue was diluted with methylene chloride and water, then brine was added to the mixture, which was let to stand for 30 minutes. Lower level was removed along with gray solids. The aqueous layer was extracted two more times with methylene dichloride. The combined organic layers were stripped until dry. The resulting gray solid was placed on a filter paper at the bottom of a coarse fritted glass funnel and washed with 100 mL of water, 800 mL of LC grade methanol and 500 mL of diethyl ether. Solids were recrystallized from minimal amount of hot toluene. Yield 5.48g (59%) of desired product. Mass spectrometry and1H NMR (CDCI2CCI2D) data were consistent with the structure of the desired product.

Reference： [1]Patent: WO2012/87960,2012,A1 .Location in patent: Page/Page column 40-41
[2]Patent: KR2019/136140,2019,A .Location in patent: Paragraph 0409-0412

2
[ 108-77-0 ]
[ 2113-57-7 ]
[ 1205748-61-3 ]

Yield	Reaction Conditions	Operation in experiment
84%		5.2 g Magnesium (0.215 mol) was introduced in 500 ml 4-necked flask, 50 g of bromobiphenyl (214 mmol) in 200 ml THF was added dropwise. The reaction mixture was heated for 1.5 h and then subsequently cooled to room temperature. Cyanuric chloride (17.2 g, 93 mmol) in 150 ml THF was introduced to the second flask,and cooled to 0C. Grignard reagent was added, and the mixture was stirred at room temperature for 12 h. After this, 150 ml of HCl was added to the reaction mixture, aqueous phase was extracted 3 times with dichloromethane. The combined organic phases washed with water, dried using Na2SO4 and evaporated. Then the residue was recrystallized from EtOH. The yield is 32.8 g (78 mmol, 84%).
65%		In THF (20ml), was prepared 3-bromo-1,1'-biphenyl (10.73l, 64.3mmol) and Mg (4.69g, 193mmol) and then refluxed for 2 hours [1,1' biphenyl]-3-solution in THF (80ml) of the Il magnesium bromide was added dropwise at 0 to a solution of 2,4,6-trichloro-1,3,5-triazine (3.96g, 21.45mmol). The reaction mixture was slowly warmed to room temperature, and stirred for 16 hours and quenched with 10% aqueous HCl. Extracted with DCM, washed with water, and dried with sodium sulfate (Na2SO4). Evaporation of the solvent by silica gel column chromatography using heptane / DCM as eluent (9/1 ~ 7/3, v / v), purified the crude product as a white solid of 2,4-di-([1,1'-biphenyl]-3-yl)-6-chloro-1,3,5-triazine (2.30g, 65%)

Reference： [1]Patent: KR2016/28524,2016,A .Location in patent: Paragraph 0221-0223
[2]Patent: JP2016/6039,2016,A .Location in patent: Paragraph 0109; 0110

3
[ 890042-13-4 ]
[ 1205748-61-3 ]
C₄₅H₂₉N₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; at 80℃; for 23h;Inert atmosphere;	Intermediate 26 (39.5 mmol) was dissolved in 0.2 L of tetrahydrofuran (THF) under a nitrogen environment, Intermediate 27 (39.5 mmol) and tetrakis(triphenylphosphine)palladium (0.46 g, 0.4 mmol) were added thereto, and the mixture was stirred. Potassium carbonate saturated in water (13.6 g, 98.8 mmol) was added thereto, and the obtained mixture was heated and refluxed at 80 C. for 23 hours. When a reaction was complete, water was added to the reaction solution, dichloromethane (DCM) was used for an extraction, anhydrous MgSO4 was used to remove moisture from an extract, and the extract was filtered and concentrated under a reduced pressure. The obtained residue was separated and purified through flash column chromatography to obtain Compound A-2 (a yield of 75%). (0188) calcd. C45H29N3: C, 88.35; H, 4.78; N, 6.87. found: C, 88.35; H, 4.78; N, 6.87.
74%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In monoethylene glycol diethyl ether; water; toluene; for 16h;Reflux; Inert atmosphere;	DME (100 ml), toluene (100 ml), and in water (10 ml), 4,4,5,5-tetramethyl-2-(triphenylene-2-yl) 1,3,2-dioxaborolane (2.53 g, 7.14 mmol), 2,4-di-([1,1'-biphenyl]-3-yl)-6-chloro-1,3,5-triazine (2.50g, 5.95mmol), Pd(PPh3)4 (0.69g, 0.60mmol), and K2CO3 (1.65g, 11.91mmol) was the solution of the reflux for 16 hours under nitrogen. After cooling to room temperature, the reaction mixture was diluted with water. The solid was collected by filtration, washed with water, ethanol, and washed with toluene, then redissolved in boiling toluene and filtered through a short plug of silica gel. Evaporation of the solvent, toluene, was re-crystallized compound 5 as a white solid (2.70g, 74%).

Reference： [1]Patent: US2018/90689,2018,A1 .Location in patent: Paragraph 0186-0188
[2]Patent: JP2016/6039,2016,A .Location in patent: Paragraph 0111

4
[ 2113-57-7 ]
[ 506-77-4 ]
[ 1205748-61-3 ]

Yield	Reaction Conditions	Operation in experiment
84%		Magnesium (0.215 mol) of 5.2 g ofInitially, 500 ml 4- nine (four-necked) Introduced into the flask, and 200 ml of THF in 50 gA solution of bromobiphenyl (214 mmol) was slowly added dropwise thereto.Heating for 1.5 hours at the boiling point of the reaction mixture, andThen allowed to cool to room temperature.The cyanogen chloride (cyanogenchloride) (17.2 g, 93 mmol) in 150 ml of THF First it introduced into a second flask and cooled to 0 . Then, the coolingIt was added dropwise a Grignard (Grignard) reagent at this temperature and the mixture was stirred at room temperature for 12 hours.After said time, and extracted three times, the aqueous phase was added to 150 ml of HCl to the reaction mixture with dichloromethane.Washing the organic phase with water, combined, dried over Na2SO4, and evaporated.The residue was recrystallized from EtOH. The yield was 32.8 g (78 mmol, 84%).

Reference： [1]Patent: KR2015/93836,2015,A .Location in patent: Paragraph 0217-0219

5
[ 1205748-61-3 ]
C₂₃H₁₆N₂ [ No CAS ]
C₅₀H₃₃N₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		3.5 g of intermediate A1A from above was slurried into 125 mL dry THF in a nitrogen filled glove box and 0.32 g sodium hydride was added with stirring. After 4 hrs, 4.725 g 1,3,5-Triazine, 2,4-bis([1,1?-biphenyl]-3-yl)-6-chloro- was added as a solid over a period of 10 mins. The slurry rapidly darkens to a deep red after heating to 40 C. The red slurry was filtered through a fine frit and the filter cake was washed with dry THF until all red color was eluted. Evaporation of the red solution yielded golden yellow crude solid of structure A2B

Reference： [1]Patent: US2016/343957,2016,A1 .Location in patent: Paragraph 0299; 0300

6
[ 1205748-61-3 ]
C₂₉H₂₁N₃ [ No CAS ]
C₅₆H₃₈N₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		3.4 g of intermediate A4A from above was slurried into 120 mL dry THF in a nitrogen filled glove box and 0.238 g sodium hydride was added with stirring. After 150 mins, 3.57 g 1,3,5-Triazine, 2,4-bis([1,1?-biphenyl]-3-yl)-6-chloro- was added. The slurry rapidly darkens to a deep red after heating to 50 C. The red slurry was filtered through a fine frit and the filter cake was washed with dry THF until all red color was eluted. Evaporation of the red solution yielded a crude golden yellow solid of structure A4B

Reference： [1]Patent: US2016/343957,2016,A1 .Location in patent: Paragraph 0311; 0312

7
[ 1205748-61-3 ]
C₃₀H₂₀N₄ [ No CAS ]
C₅₇H₃₇N₇ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		4.3 g of intermediate A5A from above was slurried into 150 mL dry THF in a nitrogen filled glove box and 0.284 g sodium hydride was added with stirring. After 30 mins, 4.21 g 1,3,5-Triazine, 2,4-bis([1,1?-biphenyl]-3-yl)-6-chloro was added as a solid over a period of 90 mins. The slurry rapidly darkens to a deep red after heating to 50 C. The red slurry was filtered through a fine frit and the filter cake was washed with dry THF until all red color was eluted. Evaporation of the red solution yielded a crude golden yellow solid of structure A5B

Reference： [1]Patent: US2016/343957,2016,A1 .Location in patent: Paragraph 0317; 0318

8
[ 108-77-0 ]
[ 103068-18-4 ]
[ 1205748-61-3 ]

Yield	Reaction Conditions	Operation in experiment
89%	In tetrahydrofuran; at 0 - 20℃;Inert atmosphere;	General procedure: 295g (1.6mol, 1.0eq) of 2,4,6-trichloro-1 ,3,5-triazine [108-77-0] 1 are solved in 800ml dried THF in a four-necked flask under an inert atmosphere. The solution is cooled with an ice bath to about 0C and 800ml (1.6mol, 1.0eq) of a 2mol/l phenylmagnesiumchloride solution are added slowly to maintain the temperature below 10C. Then, the mixture is stirred at room temperature overnight and after the reaction had finished, 800ml of toluene and 1.2L of HCI 2% are added. The organic phase is separated, extracted three times with water and dried over sodium sulfate. The solvent is evaporated under reduced pressure until the product precipitates. After washing the solid with ethanol, 242g (1.1mol, 67%) of the desired product 3a are obtained. Other examples are obtained analogously:
55%	In tetrahydrofuran; at 0℃;	100.0 g (542.3 mmol) of cyanuric chloride and 700 mL of anhydrous THF were put in a 2 L flask, 361.4 mL of 3-Biphenylmagnesium bromide (3 M) was added thereto, and the mixture was slowly added thereto in a dropwise fashion at 0 C. When a reaction was complete, water was poured into the reaction solution, the mixture was stirred for 30 minutes, and an organic layer therefrom was separated, concentrated after removing moisture by using magnesium sulfate, and purified with methanol and hexane to obtain white solid Intermediate 5-1 (122.9 g, yield of 55%). (0188) calcd. C27H18ClN3: C, 77.23; H, 4.32; Cl, 8.44; N, 10.01; found: C, 77.25; H, 4.31; Cl, 8.44; N, 10.00.
55%	In tetrahydrofuran; at 0℃;	Cyanuric chloride (100.0 g, 542.3 mmol) and anhydrous THF (700 mE) were put in a 2 E flask, and 3-biphenyl magnesium bromide (3 M, 361.4 mE) was slowly added thereto in a dropwise fashion at 00 C. When the reaction wascomplete, water was poured into the reaction solution, themixture was stirred for 30 minutes, an organic layer thereinwas separated, concentrated after removing moisture withmagnesium sulfate, and punfied with methanol and hexaneto obtain an intermediate 1-9 as a white solid (122.9 g, ayield: 55%).

Reference： [1]Patent: WO2017/16630,2017,A1 .Location in patent: Page/Page column 50; 51
[2]Patent: US2017/317293,2017,A1 .Location in patent: Paragraph 0185-0188
[3]Patent: US2018/339967,2018,A1 .Location in patent: Paragraph 0175; 0176

9
[ 1205748-61-3 ]
9,9-dimethyl-9H-fluoren-4-yl-boronic acid [ No CAS ]
C₄₂H₃₁N₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In ethanol; water; toluene; at 110℃;Inert atmosphere;	30g (80mmol, 1.0eq) of 7a, 21g (88mmol, 1.1eq) 9,9-Dimethyl- 9H-fluoren-4-yl-boronic acid [1246022-50-3] and 17g (160mmol, 2.0eq) sodium carbonate are dissolved in 400ml toluene, 250ml water and 170ml ethanol under an inert atmosphere. Then, 0.93g (0.80mmol, 0.01eq) tetrakis(triphenylphosphine)palladium is added and the mixture refluxed over night at 110C. After the reaction is completed, 300ml water were added and the precipitated (36g) solid is filtered. The organic layer is separated, washed with water and dried over sodium sulfate. After evaporation of the solvent, another 5.1g of the crude product are obtained. The combined solids are purified by hot extraction from toluene/heptane, recrystallized twice from toluene/heptane and sublimed to give 20g (38mmol, 47%) of the desired product 9a.

Reference： [1]Patent: WO2017/16630,2017,A1 .Location in patent: Page/Page column 55; 56

Yield	Reaction Conditions	Operation in experiment
	With tetrakis(triphenylphosphine) palladium(0); sodium hydroxide; In tetrahydrofuran; water;Reflux;	General procedure: Sub 1-1 (14.8g, 80 mmol), THF 360 mL, Sub 1-2-1 (16.3g, 80 mmol), Pd (PPh 3 )4 (2.8g, 2.4mmol), NaOH (9.6g, 240mmol ), followed by the addition of 180 mL of water, it was refluxed with stirring. When the reaction was complete, the ether was extracted with water and the organic layer is MgSO 4 dried and concentrated and then the produced organic silicagel column and recrystallized to give the product 12.3g (68%). Sub 1-3-1 (12.2g, 54 mmol), Sub 1-4-1 (11.0g, 54 mmol) for the synthesis in the same manner as in the Sub 1-3-1 and recrystallized product was 9.5g (66% ) it was obtained.

11
[ 1205748-61-3 ]
C₄₂H₃₉BO₂ [ No CAS ]
C₆₃H₄₃N₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,4-dioxane; water; at 60℃; for 12h;Inert atmosphere;	The intermediate 1-9 (3.0 g, 7.1 mmol), the intermediate 1-4 (5.0 g, 8.6 mmol), potassium carbonate (2.5 g, 17.9 mmol), and tetrakis(triphenylphosphine) palladium (0) (0.3 g, 0.2 mmol) were added to 1,4-dioxane (20 mE) and water (10 mE) in a 100 mE flask, and the mixture was heated at 60 C. under a nitrogen flow for 12 hours. The obtained mixture was added to methanol (100 mE), a solid crystallized therein was filtered, dissolved in toluene, filtered through silica gel/Celite, and then, recrystallized with methanol after removing an appropriate amount of an organic solvent to obtain a compound 6 (4.07 g, a yield:68%). calcd. C63H43N3: C, 89.86; H, 5.15; N, 4.99.found: C, 89.86; H, 5.15; N, 4.98.

Reference： [1]Patent: US2018/339967,2018,A1 .Location in patent: Paragraph 0175; 0177; 0178

12
[ 1205748-61-3 ]
C₄₂H₃₉BO₂ [ No CAS ]
C₆₃H₄₃N₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,4-dioxane; water; at 60℃; for 12h;Inert atmosphere;	The intermediate 1-9 (3.0 g, 7.1 mmol), the intermediate 1-14 (5.0 g, 8.6 mmol), potassium carbonate (2.5 g, 17.9 mmol), and tetrakis(triphenylphosphine) palladium (0) (0.3 g, 0.2 mmol) were added to 1,4-dioxane (20 mE) and water (10 mE) in a 100 mE flask, and the mixture was heated at 60 C. under a nitrogen atmosphere for 12 hours. The obtained mixture was added to methanol (100 mE), a solid crystallized therein was filtered, dissolved in toluene, filtered through silica gel/Celite, and recrystallized with methanol afier removing an appropriate amount of an organic solvent to obtain a compound 14 (4.19 g, a yield: 70%). calcd. C63H43N3: C, 89.86; H, 5.15; N, 4.99.found: C, 89.84; H, 5.15; N, 4.99.

Reference： [1]Patent: US2018/339967,2018,A1 .Location in patent: Paragraph 0196-0198

13
[ 1205748-61-3 ]
C₁₈H₁₃NSSi [ No CAS ]
C₄₅H₃₀N₄SSi [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate; In toluene; for 3h;Reflux;	General procedure: Sub 1-1 (11.6 g, 33.62 mmol), Sub 2-1 (5.27 g, 33.62 mmol), Pd2 (dba) 3 (1 g, 0.1 mmol)(t-Bu) 3P(0.4 g, 0.002 mmol),After NaOt-Bu (9.61 g, 100 mmol) was dissolved in anhydrous toluene,And refluxed for 3 hours.When the reaction is completed, the temperature of the reaction is cooled to room temperature,Extracted with CH2Cl2 and wiped with water.A small amount of water was removed with anhydrous MgSO4, filtered under reduced pressure, and the organic solvent was concentrated to give the productThe silicagel column and desired by recrystallization11.5 g of P1-1 was obtained. (Yield: 80%).

Reference： [1]Patent: KR2019/1967,2019,A .Location in patent: Paragraph 0206; 0210; 0244-0246

14
[ 1205748-61-3 ]
C₂₂H₁₅NSSi [ No CAS ]
C₄₉H₃₂N₄SSi [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate; In toluene; at 100℃; for 3h;	General procedure: Sub 1-1 (13.3 g, 33.62 mmol), Sub 2-1 (5.27 g, 33.62 mmol), Pd2 (dba) 3 (1 g, 0.1 mmol)(t-Bu) 3P (0.4 g, 0.002 mmol),NaOt-Bu (9.61 g, 100 mmol) was added to a solution ofAfter dissolving in anhydrous toluene,And refluxed for 3 hours.When the reaction is completed, the temperature of the reaction is cooled to room temperature,Extracted with CH2Cl2 and wiped with water. A small amount of water was removed with anhydrous MgSO 4, filtered under reduced pressure, and the organic solvent was concentrated. The resulting product was purified by silicagel column and recrystallized to obtain 12.38 g of desired P 1-1 (yield: 78%).

Reference： [1]Patent: KR2019/10811,2019,A .Location in patent: Paragraph 0205; 0206; 0208-0210; 0236-0238

15
[ 1205748-61-3 ]
[ 2450449-30-4 ]
[ 2450445-32-4 ]

Yield	Reaction Conditions	Operation in experiment
75%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In tetrahydrofuran; water for 12h; Reflux;	8 [Synthesis Example 2] Synthesis of Compound A-08 Target compound of Preparation Example 6 (5.0 g, 11.7 mmol), 2,4-di([1,1'-biphenyl]-3-yl)-6-chloro-1,3,5-triazine (6.4 g, 15.2 mmol) and Pd(PPh3)4(0.7 g, 0.6 mmol), K2CO3(4.9 g, 35.2 mmol) wereadded to a mixture solution ofTHF 100ml and H2O 30ml and heated to reflux for 12 hours.After completion of the reaction, the mixture was extracted with methylene chloride, MgSO4was added and filtered.After removing the solvent of the filtered organic layer, A-08 (6.0 g, yield 75%) as a target compound was obtained using column chromatography.

Reference： [1]Current Patent Assignee: SOLUS ADVANCED MATERIALS CO LTD - KR2020/76814, 2020, A Location in patent: Paragraph 0252-0255

16
[ 1205748-61-3 ]
[ 2173555-59-2 ]
[ 2639694-39-4 ]

Yield	Reaction Conditions	Operation in experiment
60%	With bis(tri-t-butylphosphine)palladium⁽⁰⁾; potassium carbonate In tetrahydrofuran; water for 11h; Inert atmosphere; Reflux;	30 Example 30: Preparation of compound 30 In a nitrogen atmosphere, compound sub_a-20 (15 g, 35.7 mmol) and compound sub_b-26 (9.7 g, 39.3 mmol) were added to THF (300 ml), followed by stirring and refluxing.Thereafter, potassium carbonate (19.7 g, 142.9 mmol) was dissolved in 59 ml of water, and after sufficiently stirring, bis (tri-tert-butylphosphine) palladium (0) (0.4 g, 0.7 mmol) was added.After the reaction for 11 hours, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled.This was again dissolved in chloroform, washed twice with water, and the organic layer was separated, anhydrous magnesium sulfate was added thereto, stirred, filtered, and the filtrate was distilled under reduced pressure.The concentrated compound was purified by silica gel column chromatography to prepare compound sub30 (12.5 g, yield 60%)

Reference： [1]Current Patent Assignee: LG CHEM CO.,LTD. - KR2021/36857, 2021, A Location in patent: Paragraph 0389-0392

17
[ 1205748-61-3 ]
[ 2173555-59-2 ]
[ 2639692-97-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: potassium carbonate; bis(tri-t-butylphosphine)palladium⁽⁰⁾ / tetrahydrofuran; water / 11 h / Inert atmosphere; Reflux 2: bis(tri-t-butylphosphine)palladium⁽⁰⁾; sodium t-butanolate / 5,5-dimethyl-1,3-cyclohexadiene / 2 h / Inert atmosphere; Reflux

Reference： [1]Current Patent Assignee: LG CHEM CO.,LTD. - KR2021/36857, 2021, A

18
[ 1205748-61-3 ]
[ 2244899-49-6 ]
[ 2244899-23-6 ]

Yield	Reaction Conditions	Operation in experiment
71%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In 1,4-dioxane; water at 120℃; for 3h;	7 Preparation of compound 1 General procedure: One neck round bottom flask (One neck r.b.f)9-(7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)dibenzo[b,d]furan-4-yl)-9H-carbazole(12.5 g, 27.2 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (8.74 g, 32.6 mmol), tetrakis (triphenylphosphine) palladium (0) (3.1 g) , 2.72 mmol), potassium carbonate (7.5 g, 54.5 mmol), and 1,4-dioxane/water (150 ml/30 ml) mixture was refluxed at 120° C. for 3 hours. After filtering at 120°C, it was washed with 1,4-dioxane, distilled water, and MeOH at 120°C.Washed to obtain compound 1 (C) (11.2 g, over two step 71%)

Reference： [1]Current Patent Assignee: LT SAMBO CO LTD - KR102143580, 2020, B1 Location in patent: Paragraph 0352-0353; 0368-0369; 0379-0382; 0385

19
[ 1205748-61-3 ]
[ 2244899-53-2 ]
[ 2244899-29-2 ]

Yield	Reaction Conditions	Operation in experiment
59%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In 1,4-dioxane; water at 120℃; for 3h;	8 Preparation of compound 1 General procedure: One neck round bottom flask (One neck r.b.f)9-(7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)dibenzo[b,d]furan-4-yl)-9H-carbazole(12.5 g, 27.2 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (8.74 g, 32.6 mmol), tetrakis (triphenylphosphine) palladium (0) (3.1 g) , 2.72 mmol), potassium carbonate (7.5 g, 54.5 mmol), and 1,4-dioxane/water (150 ml/30 ml) mixture was refluxed at 120° C. for 3 hours. After filtering at 120°C, it was washed with 1,4-dioxane, distilled water, and MeOH at 120°C.Washed to obtain compound 1 (C) (11.2 g, over two step 71%)

Reference： [1]Current Patent Assignee: LT SAMBO CO LTD - KR102143580, 2020, B1 Location in patent: Paragraph 0352-0353; 0368-0369; 0386-0389; 0392

20
[ 1205748-61-3 ]
[ 2244899-58-7 ]
[ 2244899-36-1 ]

Yield	Reaction Conditions	Operation in experiment
63%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In 1,4-dioxane; water at 120℃; for 3h;	9 Preparation of compound 1 General procedure: One neck round bottom flask (One neck r.b.f)9-(7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)dibenzo[b,d]furan-4-yl)-9H-carbazole(12.5 g, 27.2 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (8.74 g, 32.6 mmol), tetrakis (triphenylphosphine) palladium (0) (3.1 g) , 2.72 mmol), potassium carbonate (7.5 g, 54.5 mmol), and 1,4-dioxane/water (150 ml/30 ml) mixture was refluxed at 120° C. for 3 hours. After filtering at 120°C, it was washed with 1,4-dioxane, distilled water, and MeOH at 120°C.Washed to obtain compound 1 (C) (11.2 g, over two step 71%)

Reference： [1]Current Patent Assignee: LT SAMBO CO LTD - KR102143580, 2020, B1 Location in patent: Paragraph 0352-0353; 0368-0369; 0393-0396; 0399

21
[ 1205748-61-3 ]
[ 1801624-63-4 ]
[ 2413719-94-3 ]

Yield	Reaction Conditions	Operation in experiment
65%	With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate In 1,4-dioxane; water; toluene for 16h; Reflux;	T1 Example T1: 42.0 g (100 mmol) of (2,4-bis([1,1'-biphenyl]-3-yl)-6-chloro-1,3,5-triazine [1205748-61-3], 32.4 g (100 mmol) of 2- (hexahydro-6,7,8,9,10,11- -5,9: 7,11- dimethacrylate furnace -5H- benzo cyclo-nonene-2-yl) -4, 4,5,5-tetramethyl-1,3,2-dioxaborolane [1801624-63-4], 31.9 g (150 mmol) of tripotassium phosphate, 821 mg (2 mmol) of S-Phos, 225 A well-stirred mixture of mg (1 mmol) of palladium(II) acetate, 400 ml of toluene, 80 ml of dioxane and 300 ml of water is heated under reflux for 16 hours.After cooling, the organic phase is separated from the aqueous phase and washed once with 300 ml of water and once with 300 ml of saturated sodium chloride solution, then dried over magnesium sulfate.The drying agent is filtered using a silica gel bed in the form of toluene slurry, and the filtrate is concentrated to dryness. Water isextracted by stirringwith hotiso-propanol, followed by extraction with hot acetonitrile 5 times andpurified by zone sublimation underreduced pressure (p-10-5mbar, T-310° C.) Yield: 37.8 g (65 mmol) ), 65% Purity by HPLC is > 99.9%.

Reference： [1]Current Patent Assignee: MERCK KGAA - KR2021/68054, 2021, A Location in patent: Paragraph 0612-0614

22
[ 1205748-61-3 ]
[ 2763581-83-3 ]
[ 2763579-49-1 ]

Yield	Reaction Conditions	Operation in experiment
77%	With bis(tri-t-butylphosphine)palladium⁽⁰⁾; potassium carbonate In tetrahydrofuran; water for 12h; Inert atmosphere; Reflux;	9 Synthesis Example 8 Chemical formula BA (10g, 22.5mmol) and Trz7 (9.6g, 23mmol) were placed in 200ml of THF in a nitrogen atmosphere, and stirred and refluxed. After that, potassium carbonate (9.3g, 67.5mmol) was dissolved in 28ml of water and thoroughly stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.1g, 0.2mmol) was added. After the reaction for 12 hours, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 12.2 g of compound 9. (Yield 77%)

Reference： [1]Current Patent Assignee: LG CHEM, LTD. - KR2021/139185, 2021, A Location in patent: Paragraph 0511-0513

23
[ 1205748-61-3 ]
[ 2762744-23-8 ]
[ 2762743-22-4 ]

Yield	Reaction Conditions	Operation in experiment
76%	With tetrakis-(triphenylphosphine)-palladium; tetrabutylammonium bromide; potassium carbonate In ethanol; water monomer; toluene at 75 - 85℃; for 12h; Inert atmosphere;	5 (5) Synthesis of compound 100 General procedure: Into the there-necked flask equipped with mechanical stirring, thermometer and spherical condenser, nitrogen (0.100L/min) was introduced for replacement for 15min, and intermediate F-1 (5.0g, 11.9mmol), reaction H-1 (3.18g, 11.9mm) were added. mmol), tetrakis(triphenylphosphine)palladium (0.68 g, 0.59 mmol), potassium carbonate (4.92 g, 35.6 mmol), tetrabutylammonium bromide (0.16 g, 0.59 mmol), and toluene (40 mL), A mixed solvent of ethanol (20 mL) and deionized water (10 mL). The stirring was started, the temperature was raised to 75-85° C. for 12 h, and after the reaction was completed, it was cooled to room temperature. Add toluene (100 mL) for extraction, combine the organic phases, use anhydrous magnesium sulfate to dry the organic phase, filter the filtrate to remove the solvent under reduced pressure; use n-heptane as the mobile phase to purify the crude product by silica gel column chromatography, and then use dichloromethane /Ethyl acetate system was recrystallized to obtain compound 100 (4.81 g, yield 77%),

Reference： [1]Current Patent Assignee: SHAANXI LIGHTE OPTOELECTRONICS MATERIAL CO.,LTD - CN114075185, 2022, A Location in patent: Paragraph 0161; 0163; 0173

24
[ 1402225-89-1 ]
[ 5122-95-2 ]
[ 1205748-61-3 ]

Yield	Reaction Conditions	Operation in experiment
	With tetrakis-(triphenylphosphine)-palladium; potassium carbonate In tetrahydrofuran; lithium hydroxide monohydrate at 80℃; for 12h;	10 Synthesis Example 6: Synthesis of Int-4 General procedure: Combine 2,4-dichloro-6-phenyl-1,3,5-triazine (17.12 g, 75.75 mmol), [1,1'-biphenyl]-4-ylboronic acid (10 g, 50.50 mmol) moles),K2CO3 (13.96 g, 138.21 mmol) and Pd(PPh3)4 (2.92 g, 2.52 mmol) were placed in a round bottom flask,And THF (100 mL) and distilled water (50 mL) were added thereto, and then the resultant was stirred under reflux at 80° C. for 12 hours.When the reaction was completed, the mixture was added to 300 mL of methanol, and the solid crystallized therein was filtered,This was dissolved in monochlorobenzene and filtered through silica gel/diatomaceous earth, and after removal of an appropriate amount of organic solvent,Recrystallizatio

Reference： [1]Current Patent Assignee: SAMSUNG SDI CO.,LTD. - CN114437090, 2022, A Location in patent: Paragraph 0228-0236; 0245-0248

25
[ 1205748-61-3 ]
[ 2702285-28-5 ]
[ 2897651-75-9 ]

Yield	Reaction Conditions	Operation in experiment
69.6%	With tetrakis-(triphenylphosphine)-palladium; potassium carbonate In ethanol; lithium hydroxide monohydrate; toluene Reflux; Inert atmosphere;	17.1 Step 1: Synthesis of Compound A-422 In a three-necked round-bottom flask, K (4.7 g, 10.5 mmol), AD (4.2 g, 10.0 mmol), Pd(PPh3)4 (0.60 g, 0.52 mmol) and K2CO3 (4.1 g, 30.0 mmol) were added to toluene (80 mL), EtOH (20 mL) and H2O (20 mL) and heated to reflux overnight under nitrogen protection. After the reaction was finished, stopped heating, the system was cooled to room temperature and filtered through suction under reduced pressure, and the obtained solid was washed with water and methanol in sequence. The solid was recrystallized from toluene to obtain a white solid (4.9 g, 6.96 mmol) with a yield of 69.6%. The product was confirmed as the target product A-422 with a molecular weight of 703.3.
69.6%	With tetrakis-(triphenylphosphine)-palladium; potassium carbonate In ethanol; lithium hydroxide monohydrate; toluene Reflux; Inert atmosphere;	17.1 Step 1: Synthesis of Compound A-422 In a three-necked round-bottom flask, K (4.7 g, 10.5 mmol), AD (4.2 g, 10.0 mmol), Pd(PPh3)4 (0.60 g, 0.52 mmol) and K2CO3 (4.1 g, 30.0 mmol) were added to toluene (80 mL), EtOH (20 mL) and H2O (20 mL) and heated to reflux overnight under nitrogen protection. After the reaction was finished, stopped heating, the system was cooled to room temperature and filtered through suction under reduced pressure, and the obtained solid was washed with water and methanol in sequence. The solid was recrystallized from toluene to obtain a white solid (4.9 g, 6.96 mmol) with a yield of 69.6%. The product was confirmed as the target product A-422 with a molecular weight of 703.3.

Reference： [1]Current Patent Assignee: BEIJING SUMMER SPROUT TECHNOLOGY CO; BEIJING SUMMER SPROUT TECHNOLOGY CO LTD - US2022/194956, 2022, A1 Location in patent: Paragraph 0278-0279
[2]Current Patent Assignee: BEIJING SUMMER SPROUT TECHNOLOGY CO; BEIJING SUMMER SPROUT TECHNOLOGY CO LTD - US2022/194956, 2022, A1 Location in patent: Paragraph 0278-0279

26
[ 1205748-61-3 ]
[ 2933913-82-5 ]
[ 2933913-83-6 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: C₂₆H₁₃ClN₂ With sodium hydride In dimethyl sulfoxide Inert atmosphere; Stage #2: 2,4-bis(biphenyl-3-yl)-6-chloro-1,3,5-triazine In dimethyl sulfoxide at 45℃; Inert atmosphere;	1.6 Step 6: Preparation of Intermediate Int-6 Under nitrogen protection, 10.0 mmol of intermediate Int-5 was dissolved in 40 mL of dry DMSO,12.0 mmol of 65% sodium hydride solid was added, and the reaction was stirred for 30 minutes.Then add 12.0 mmol of 2-chloro-4,6-diphenyl-1,3,5-triazine (reactant 3),The temperature was raised to 45°C and the reaction was stirred for 12 hours.down to room temperature,The reaction solution was poured into 150 mL of ice water, filtered, the filter cake was washed with water and ethanol, and separated and purified with a silica gel column to obtain a yellow solid Int-6 with a yield of 87%.

Reference： [1]Current Patent Assignee: SHANGHAI BAYI SPACE TIME ADVANCED MAT - CN115073461, 2022, A Location in patent: Paragraph 0085-0086; 0108-0110

27
[ 1205748-61-3 ]
[ 2897672-96-5 ]
[ 2897672-98-7 ]

Yield	Reaction Conditions	Operation in experiment
75 %	With palladium diacetate; 1,2-bis-(diphenylphosphino)ethane; potassium iodide In N,N-dimethyl-formamide at 90℃; Inert atmosphere;	2 The third step: the preparation of intermediate Int-8 Under nitrogen protection, 20.0 mmol of Int-7 was dissolved in 50 mL of DMF, 22.0 mmol of 2-chloro-4,6-diphenyl-1,3,5-triazine, 20.0 mmol of potassium iodide, 2.0 1 mmol of palladium acetate and 4.0 mmol of DPPE, raised to 90°C and stirred for 12 hours, cooled to room temperature, poured the reaction liquid into 150 mL of water, filtered, washed the filter cake with water and ethanol, and separated the solid with a silica gel column Purified to obtain the intermediate Int-8, G is O, the yield is 75%; G is S, the yield is 77%

Reference： [1]Current Patent Assignee: BEIJING BAYI SHIKONG YEJING MATERIAL SCIENCE AND TECHNOLOGY CO., LTD. - CN115677671, 2023, A Location in patent: Paragraph 0120; 0128-0130

28
[ 1205748-61-3 ]
[ 2926562-03-8 ]
[ 2926559-49-9 ]

Yield	Reaction Conditions	Operation in experiment
67 %	With bis(tri-tert-butylphosphine)palladium⁽⁰⁾; potassium carbonate In tetrahydrofuran; water Reflux;	70 Synthesis Example 70 Trz54 (15g, 35.7mmol) and compound A-9-3 (12.9g, 37.5mmol) were added to 300ml of THF, stirred and refluxed. Thereafter, potassium carbonate (14.8g, 107.2mmol) was dissolved in 100ml of water, and after stirring sufficiently, bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.4mmol) was added. After reacting for 3 hours, the mixture was cooled to room temperature, and the organic layer was distilled after separating the organic layer and the water layer. This was dissolved in chloroform again, and after washing twice with water, the organic layer was separated, stirred with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 14.4 g of Compound 70. (yield 67%)

Reference： [1]Current Patent Assignee: LG CHEM CO.,LTD. - WO2023/85835, 2023, A1 Location in patent: Paragraph 543-545

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Technical Information

• Acid-Catalyzed α -Halogenation of Ketones • Addition of a Hydrogen Halide to an Internal Alkyne • Alcohols from Haloalkanes by Acetate Substitution-Hydrolysis • Alkyl Halide Occurrence • Alkylation of an Alkynyl Anion • An Alkane are Prepared from an Haloalkane • Benzylic Oxidation • Birch Reduction • Birch Reduction of Benzene • Blanc Chloromethylation • Chloroalkane Synthesis with SOCI2 • Complete Benzylic Oxidations of Alkyl Chains • Complete Benzylic Oxidations of Alkyl Chains • Conversion of Amino with Nitro • Convert Haloalkanes into Alcohols by SN2 • Deprotonation of Methylbenzene • Directing Electron-Donating Effects of Alkyl • Electrophilic Chloromethylation of Polystyrene • Friedel-Crafts Alkylation of Benzene with Acyl Chlorides • Friedel-Crafts Alkylation of Benzene with Carboxylic Anhydrides • Friedel-Crafts Alkylation of Benzene with Haloalkanes • Friedel-Crafts Alkylation Using Alkenes • Friedel-Crafts Alkylations of Benzene Using Alkenes • Friedel-Crafts Alkylations Using Alcohols • Friedel-Crafts Reaction • General Reactivity • Grignard Reaction • Groups that Withdraw Electrons Inductively Are Deactivating and Meta Directing • Halogenation of Alkenes • Halogenation of Benzene • Hiyama Cross-Coupling Reaction • Hydrogenation to Cyclohexane • Hydrogenolysis of Benzyl Ether • Kinetics of Alkyl Halides • Kumada Cross-Coupling Reaction • Methylation of Ammonia • Nitration of Benzene • Nucleophilic Aromatic Substitution • Nucleophilic Aromatic Substitution with Amine • Oxidation of Alkyl-substituted Benzenes Gives Aromatic Ketones • Preparation of Alkylbenzene • Reactions of Alkyl Halides with Reducing Metals • Reactions of Amines • Reactions of Benzene and Substituted Benzenes • Reductive Removal of a Diazonium Group • Reverse Sulfonation——Hydrolysis • Stille Coupling • Substitution and Elimination Reactions of Alkyl Halides • Sulfonation of Benzene • Suzuki Coupling • The Acylium Ion Attack Benzene to Form Phenyl Ketones • The Claisen Rearrangement • The Nitro Group Conver to the Amino Function • Vilsmeier-Haack Reaction

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P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 1205748-61-3 ] {[proInfo.proName]}

Quality Control of [ 1205748-61-3 ]

Related Doc. of [ 1205748-61-3 ]

Product Details of [ 1205748-61-3 ]

Calculated chemistry of [ 1205748-61-3 ] Expand+

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 1205748-61-3 ]

Application In Synthesis of [ 1205748-61-3 ]

[ 1205748-61-3 ] Synthesis Path-Upstream 1~3

[ 1205748-61-3 ] Synthesis Path-Downstream 1~28

Technical Information

Related Functional Groups of [ 1205748-61-3 ]

Aryls

Chlorides

Related Parent Nucleus of [ 1205748-61-3 ]

Triazines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 1205748-61-3 ]

Related Parent Nucleus of
[ 1205748-61-3 ]