[ CAS No. 618442-57-2 ] {[proInfo.proName]}

Name: 618442-57-2|9-Phenyl-3,6-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole|97%
Brand: Ambeed
SKU: A302502
Price: 8.0 USD
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Quality Control of [ 618442-57-2 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 618442-57-2 ]

Product Details of [ 618442-57-2 ]

CAS No. :	618442-57-2	MDL No. :	MFCD28015750
Formula :	C₃₀H₃₅B₂NO₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	BMKVLWGCSCKZTD-UHFFFAOYSA-N
M.W :	495.23	Pubchem ID :	12177223
Synonyms :

Calculated chemistry of [ 618442-57-2 ]

Physicochemical Properties

Num. heavy atoms :	37
Num. arom. heavy atoms :	19
Fraction Csp3 :	0.4
Num. rotatable bonds :	3
Num. H-bond acceptors :	4.0
Num. H-bond donors :	0.0
Molar Refractivity :	153.73
TPSA :	41.85 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	Yes
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	Yes
Log Kp (skin permeation) :	-4.37 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	6.97
Log Po/w (WLOGP) :	5.38
Log Po/w (MLOGP) :	3.43
Log Po/w (SILICOS-IT) :	3.94
Consensus Log Po/w :	3.94

Druglikeness

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

Water Solubility

Log S (ESOL) :	-7.48
Solubility :	0.0000163 mg/ml ; 0.0000000328 mol/l
Class :	Poorly soluble
Log S (Ali) :	-7.66
Solubility :	0.0000108 mg/ml ; 0.0000000217 mol/l
Class :	Poorly soluble
Log S (SILICOS-IT) :	-9.68
Solubility :	0.000000105 mg/ml ; 0.0000000002 mol/l
Class :	Poorly soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	2.0
Synthetic accessibility :	4.06

Safety of [ 618442-57-2 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 618442-57-2 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 618442-57-2 ]
Downstream synthetic route of [ 618442-57-2 ]

[ 618442-57-2 ] Synthesis Path-Upstream 1~7

1
[ 61676-62-8 ]
[ 57103-20-5 ]
[ 618442-57-2 ]

Reference： [1] Journal of Materials Chemistry, 2011, vol. 21, # 25, p. 9139 - 9148
[2] Organic Letters, 2006, vol. 8, # 22, p. 5033 - 5036
[3] Tetrahedron Letters, 2005, vol. 46, # 5, p. 855 - 858

2
[ 61676-62-8 ]
[ 618442-57-2 ]

Reference： [1] Patent: US7094902, 2006, B2, . Location in patent: Page/Page column 101

3
[ 73183-34-3 ]
[ 57103-20-5 ]
[ 618442-57-2 ]

Yield	Reaction Conditions	Operation in experiment
45%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium acetate In 1,4-dioxane for 5 h; Reflux	3,6-dibromo-N-phenylcarbazole (0.075 mol) was dissolved in 300 ml of dioxane,Under the addition of bis (pinacolato) diboron (0.164 mol)Potassium acetate (0.375 mol),Tetrakis (triphenylphosphine) palladium (0.00075 mol)And heated to reflux reaction 5h,The reaction was complete and the reaction was quenched and the reaction was quenched with dichloromethane and water. The organic phase was passed through a silica gel funnel and the organic phase was dried under reduced pressure. The resulting solid was subjected to column chromatography to give compound 203-1 (yield 45percent)

Reference： [1] Patent: CN106928237, 2017, A, . Location in patent: Paragraph 0212; 0213; 0214

4
[ 109-72-8 ]
[ 61676-62-8 ]
[ 57103-20-5 ]
[ 618442-57-2 ]

Reference： [1] Patent: US7271406, 2007, B2,

5
[ 591-50-4 ]
[ 618442-57-2 ]

Reference： [1] Journal of Materials Chemistry, 2011, vol. 21, # 25, p. 9139 - 9148

6
[ 1150-62-5 ]
[ 618442-57-2 ]

Reference： [1] Journal of Materials Chemistry, 2011, vol. 21, # 25, p. 9139 - 9148

7
[ 86-74-8 ]
[ 618442-57-2 ]

Reference： [1] Journal of Materials Chemistry, 2011, vol. 21, # 25, p. 9139 - 9148

[ 618442-57-2 ] Synthesis Path-Downstream 1~32

1
[ 61676-62-8 ]
[ 57103-20-5 ]
[ 618442-57-2 ]

Reference： [1]Journal of Materials Chemistry,2011,vol. 21,p. 9139 - 9148
[2]Organic Letters,2006,vol. 8,p. 5033 - 5036
[3]Tetrahedron Letters,2005,vol. 46,p. 855 - 858

2
[ 406461-39-0 ]
[ 618442-57-2 ]
3,6-bis-[2-(4-tert-butyl-phenyl)-pyrimidin-5-yl]-9-phenyl-9H-carbazole [ No CAS ]

Reference： [1]Tetrahedron Letters,2005,vol. 46,p. 855 - 858

3
[ 1829-28-3 ]
[ 618442-57-2 ]
[ 915224-45-2 ]

Reference： [1]Organic Letters,2006,vol. 8,p. 5033 - 5036

4
[ 618442-57-2 ]
C₆₀H₄₅N [ No CAS ]

Reference： [1]Organic Letters,2006,vol. 8,p. 5033 - 5036

5
[ 618442-57-2 ]
(2-{6-[2-(hydroxy-di-p-tolyl-methyl)-phenyl]-9-phenyl-9H-carbazol-3-yl}-phenyl)-di-p-tolyl-methanol [ No CAS ]

Reference： [1]Organic Letters,2006,vol. 8,p. 5033 - 5036

6
[ 61676-62-8 ]
[ 618442-57-2 ]

Yield	Reaction Conditions	Operation in experiment
		Example 21 Preparation of a Poly(carbazole-co-phenylene) Block-Copolymer Part A Synthesis of 9-Phenyl-3,6-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole A 2L flask was charged with 600 mL dry THF and 3,6-dibromo-9-phenylcarbazole (60 g, 0.15 mole). This was cooled to -78° C. with an acetone-dry ice bath. n-Butyllithium (138 mL of a 2.5M solution in hexanes, 0.34 mole) was added drop-wise via syringe. The reaction was stirred for 20 minutes and then warmed to -50° C. The temperature was reduced to -78° C. and 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (64 g, 0.34 mole) added via syringe at such a rate as to maintain the temperature below -60° C. The temperature was maintained at -78° C. for two hours and then poured into an aqueous solution of ammonium acetate (90 g in 2100 mL water). The layers were phase separated and the aqueous phase extracted with methy tert-butyl ketone (2200 mL). The combined organic phase and extracts were washed with brine (2200 mL) and dried over magnesium sulfate. Concentration and re-crystallization of the resulting solid from acetone gave pure 9-phenyl-3,6-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole (PBTDC).

Reference： [1]Patent: US7094902,2006,B2 .Location in patent: Page/Page column 101

7
[ 57103-20-5 ]
[ 618442-57-2 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
	With Aliquat 336 In toluene for 12h; Heating / reflux;	21.B Part B; Preparation of Borolane Terminated Poly(9-phenylcarbazole) Pre-polymers;The reaction of PBTDC from Part A, 2M Na2CO3 (42.4 g), Aliquat 336 (tricaprylylmethylammonium chloride) (1.28 g) and 3,6-dibromo-9-phenylcarbazole (DBPC) in 100 mL toluene under standard Suzuki coupling conditions using the amounts of PBTDC and DBPC shown in Table 1 gave oligomers with 8.75 and 2.75 repeat units, respectively, as determined by NMR spectroscopy. Standard Suzuki coupling conditions and work-up included a nitrogen purge, addition of tetrakis(triphenylphosphine)palladium (0) (0.06 g), refluxing for 12 hours, pouring the resulting cooled reaction mixture into water, separating and extracting the organic layer with methylene chloride, and pouring the combined orgainic layers into about 500 mL of methanol to precipitate the solid product. TABLE 1 Oligomer Repeat Units as a Function of Reactant Amounts. PBTDC DBPC PBTDC/ monomer monomer DBPC molar Pre-polymer Number of (g) (g) ratio Yield (g) Repeat Units 7.41 3.0 2:1 2.05 8.75 11.1 3.0 3:1 3.82 2.75

Reference： [1]Current Patent Assignee: 3M CO - US7094902, 2006, B2 Location in patent: Page/Page column 101-102

8
[ 109-72-8 ]
[ 61676-62-8 ]
[ 57103-20-5 ]
[ 618442-57-2 ]

Yield	Reaction Conditions	Operation in experiment
	With ammonium acetate; In tetrahydrofuran; water; acetone;	Part B: Synthesis of 9-Phenyl-3,6-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole A 2 L flask was charged with 600 mL dry THF and 3,6-dibromo-9-phenylcarbazole (60 g, 0.15 mole). This was cooled to -78° C. with an acetone-dry ice bath. n-Butyllithium (138 mL of a 2.5M solution in hexanes, 0.34 mole) was added drop-wise via syringe. The reaction was stirred for 20 minutes and then warmed to -50° C. The temperature was reduced to -78° C. and 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (64 g, 0.34 mole) added via syringe at such a rate as to maintain the temperature below -60° C. The temperature was maintained at -78° C. for two hours and then poured into an aqueous solution of ammonium acetate (90 g in 2100 mL water). The layers were phase separated and the aqueous phase extracted with methyl-t-butyl ether (2200 mL). The combined organic phase and extracts were washed with brine (2200 mL) and dried over magnesium sulfate. Concentration and re-crystallization of the solid obtained from acetone gave pure 9-phenyl-3,6-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole. This compound can be used to modify the hole transport properties of for example the compound of Example 17. To do this 9-Phenyl-3,6-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole is used in place of 2-[9,9-dioctyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-fluoren-2-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane in Example 17.

Reference： [1]Patent: US7271406,2007,B2

9
[ 171408-76-7 ]
[ 618442-57-2 ]
[ 1004758-60-4 ]

Reference： [1]Journal of the American Chemical Society,2008,vol. 130,p. 634 - 639

10
[ 2620-76-0 ]
[ 618442-57-2 ]
[ 1258780-50-5 ]

Reference： [1]Journal of Materials Chemistry,2010,vol. 20,p. 10113 - 10119

11
[ 591-50-4 ]
[ 618442-57-2 ]

Reference： [1]Journal of Materials Chemistry,2011,vol. 21,p. 9139 - 9148

12
[ 1150-62-5 ]
[ 618442-57-2 ]

Reference： [1]Journal of Materials Chemistry,2011,vol. 21,p. 9139 - 9148

13
[ 1564-64-3 ]
[ 618442-57-2 ]
[ 1314320-95-0 ]

Reference： [1]Journal of Materials Chemistry,2011,vol. 21,p. 9139 - 9148

14
[ 86-74-8 ]
[ 618442-57-2 ]

Reference： [1]Journal of Materials Chemistry,2011,vol. 21,p. 9139 - 9148

15
[ 760212-58-6 ]
[ 618442-57-2 ]
[ 1352413-42-3 ]

Reference： [1]Journal of Materials Chemistry,2011,vol. 21,p. 19249 - 19256

16
[ 1173654-26-6 ]
[ 618442-57-2 ]
[ 1499166-96-9 ]

Reference： [1]RSC Advances,2013,vol. 3,p. 13891 - 13900

17
[ 760212-40-6 ]
[ 618442-57-2 ]
[ 1499166-97-0 ]

Reference： [1]RSC Advances,2013,vol. 3,p. 13891 - 13900

Yield	Reaction Conditions	Operation in experiment
77%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 95℃; for 24h;	General procedure: Intermediate 1-4 (3.0 g, 0.008 mol) in bis (pinacolato) dibron (2.5 g, 0.010 mol), PdCl2 (dppf) (0.3 g, 0.0004 mol), potassium-acetate (2.2 g, 0.016 mol) in 1, 4-dioxane 80 mL was put into the reaction stirred for 24 hours at 95 . After the reaction cooled to H20: After layer separation the MC column purification (n-Hexane: MC) to afford intermediate 1-4 '2.5 g (yield 71percent). (M / z = 436)
70%	With phosphoric acid; for 5h;	General procedure: Intermediate A-1 (3.1 g, 0.010 mol) dissolved in 50 mL of concentrated H3PO4 it was stirred for 5 hours. 100 mL of water and this ethyl acetate and extracted with 100 mL , and dried under reduced pressure and the organic layer . This was recrystallized in 100 mL EtOH Intermediate A - 2 ( 2.1g, to give a 72percent)

19
C₂₂H₁₇BrN₂ [ No CAS ]
[ 618442-57-2 ]
C₆₂H₄₅N₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate; In toluene; at 95℃; for 4h;	General procedure: Intermediate 1-4 '(3.0 g, 0.007 mol) in 1,4-dibromobenzene (1.3 g, 0.006 mol) Pd (dba) 2 (0.5 g, 0.00006 mol), sodium-tert-butoxide (2.2 g, 0.022 mol) Tol put in 80 mL was reacted with stirring for 4 hours at 95 . After the reaction cooled to H2O: After layer separation the MC column purification (n-Hexane: MC) to afford 2.1 g of Intermediate 1-5 (yield 77percent) (m / z = 465). Intermediate 1-4 (6.0 g, 0.016 mol), intermediate 8-2 (5.0 g, 0.010 mol) into the Example 1-Preparation Example 6 in the same manner as used in the synthesis 4.8 g (yield: to give a 70percent).

Reference： [1]Patent: KR2015/133097,2015,A .Location in patent: Paragraph 0216; 0217; 0303; 0304

20
[ 1333316-06-5 ]
[ 618442-57-2 ]
C₆₆H₅₇N₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%		A 500 mL three-neck round-bottom flask was filled with nitrogen, and then Compound C (61.8 mmol, 25.0 g), Compound G (28.1 mmol, 13.9 g), 250 mL of tetrahydrofuran (THF), and 125 mL of ethanol (EtOH) were added thereto, and the resulting mixture was stirred for 30 minutes. Further, potassium carbonate (K2CO3) (224.8 mmol, 31.1 g) was dissolved in 125 mL of water (H2O), and then the resulting solution was added to the 500 mL three-neck round-bottom flask. Subsequently, tetrakis(triphenylphosphine)palladium (Pd(PPh3)4) (2.2 mmol, 2.6 g) was added to the 500 mL three-neck round-bottom flask, and then the resulting mixture was refluxed for 6 hours while the light is blocked.[0131] The reaction mixture was cooled, and then extracted by using ethyl acetate (EA) and distilled water and concentrated, the concentrate was dissolved in 125 mL of tetrahydrofuran (THF), and the resulting solution was put into 1,250 mL of methanol and stirred for 20 minutes, and then filtered, thereby obtaining 21.3 g of a pale brown solid Compound 5 (yield 85percent).

Reference： [1]Patent: KR101503431,2015,B1 .Location in patent: Paragraph 0185-0188

21
C₁₆H₈ClN₃ [ No CAS ]
[ 618442-57-2 ]
C₅₀H₂₇N₇ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
35%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; water; toluene; for 5h;Inert atmosphere; Reflux;	According to the preparation of compound 180-1 of step (1) in Example 10,the difference is,Using compound 203-1 instead of N-phenylcarbazole-3-boronic acid,Using compound 1-5 instead of 3-bromocarbazole,To give compound 203 (yield 35percent) 3-Bromocarbazole (0.1219 mol) was dissolved in 300 ml of toluene,And N-phenylcarbazole-3-boronic acid (0.1209 mol) was added under nitrogen,30 ml of ethanol,Potassium carbonate (0.2418 mol),30ml water,Tetrakis (triphenylphosphine) palladium (0.00122 mol)And then heated to reflux reaction 5h,HPLC reaction is completed, the reaction solution spin and add dichloromethane and water extraction, take the organic phase of silica gel funnel,The organic phase was dried under reduced pressure to give compound 180-1 (yield 78percent) by column chromatography.

Reference： [1]Patent: CN106928237,2017,A .Location in patent: Paragraph 0199; 0200; 0210; 0211; 0212; 0215; 0216

22
[ 73183-34-3 ]
[ 57103-20-5 ]
[ 618442-57-2 ]

Yield	Reaction Conditions	Operation in experiment
45%	With tetrakis(triphenylphosphine) palladium(0); potassium acetate; In 1,4-dioxane; for 5h;Reflux;	3,6-dibromo-N-phenylcarbazole (0.075 mol) was dissolved in 300 ml of dioxane,Under the addition of bis (pinacolato) diboron (0.164 mol)Potassium acetate (0.375 mol),Tetrakis (triphenylphosphine) palladium (0.00075 mol)And heated to reflux reaction 5h,The reaction was complete and the reaction was quenched and the reaction was quenched with dichloromethane and water. The organic phase was passed through a silica gel funnel and the organic phase was dried under reduced pressure. The resulting solid was subjected to column chromatography to give compound 203-1 (yield 45percent)

Reference： [1]Patent: CN106928237,2017,A .Location in patent: Paragraph 0212; 0213; 0214

23
[ 59214-70-9 ]
[ 618442-57-2 ]
C₃₄H₂₁NO₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In water; toluene; for 12h;Inert atmosphere; Reflux;	9-phenyl-3,6-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -9H-carbazole 10.0 g (20.19 mmol) of8.75 g (44.42 mmol) of 3-bromobenzofurane, 12.28 g (88.85 mmol) of K2CO3, Pd (PPh3) 4 0.47 g (0.40 mmmol)100 ml of toluene,Suspended in distilled water (50 ml), and stirred under reflux for 12 hours under a stream of nitrogen.After completion of the reaction, the reaction solution was extracted with dichloromethane, filtered through silica gel, and distilled under reduced pressure. Then, hexane: dichloromethane = 7: 3 (v / v) To obtain 6.7 g (Yield: 70percent) of Compound 17

Reference： [1]Patent: KR2017/134050,2017,A .Location in patent: Paragraph 0197-0200

24
[ 7342-82-7 ]
[ 618442-57-2 ]
C₃₄H₂₁NS₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
71%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In water; toluene; for 12h;Reflux; Inert atmosphere;	9-phenyl-3,6-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -9H-carbazole 10.0 g (20.19 mmol)9.47 g (44.42 mmol) of 3-bromobenzothiophene,12.28 g (88.85 mmol) of K2CO3, Pd (PPh3) 4 0.47 g (0.40 mmmol) 100 ml of toluene,Suspended in distilled water (50 ml), and stirred under reflux for 12 hours under a stream of nitrogen. After completion of the reaction, the reaction solution was extracted with dichloromethane, filtered through silica gel, and distilled under reduced pressure. Then, hexane: dichloromethane = 7: 3 (v / v)To obtain Compound 217.3 g (Yield: 71percent).

Reference： [1]Patent: KR2017/134050,2017,A .Location in patent: Paragraph 0202-0205

25
[ 607740-08-9 ]
[ 618442-57-2 ]
C₈₀H₅₀N₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
22.3%		Under a nitrogen stream3,6-bis (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -9-phenylcarbazole 10.0 gmmol),4- (3,5-Dibromo-phenyl) -2,6-diphenyl-pyrimidine 9.41 g (20.19 mmol) K2CO3 16.7 g,800 ml of toluene,Then, 200 ml of a mixed solution was put into a 2-liter 2-neck round bottom flask, stirred for 30 minutes at room temperature,Pd (PPh3) 4 (70 mg, 0.61 mmol) was added thereto and refluxed for 18 hours.After the reaction was completed, the reaction mixture was extracted with methylene chloride, added with MgSO 4 and filtered.After removal of the solvent of the obtained organic layer, the residue was purified by column chromatography to obtain the target compound Macrocycle-II (4.93 g, yield 22.3percent).

Reference： [1]Patent: KR101847236,2018,B1 .Location in patent: Paragraph 0077-0080

26
[ 607740-08-9 ]
[ 618442-57-2 ]
C₁₆₀H₁₀₀N₁₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
2.6 g		Under a nitrogen stream3,6-bis (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -9-phenylcarbazole 10.0 gmmol),4- (3,5-Dibromo-phenyl) -2,6-diphenyl-pyrimidine 9.41 g (20.19 mmol) K2CO3 16.7 g,800 ml of toluene,Then, 200 ml of a mixed solution was put into a 2-liter 2-neck round bottom flask, stirred for 30 minutes at room temperature,Pd (PPh3) 4 (70 mg, 0.61 mmol) was added thereto and refluxed for 18 hours.After the reaction was completed, the reaction mixture was extracted with methylene chloride, added with MgSO 4 and filtered.After removal of the solvent of the obtained organic layer, the residue was purified by column chromatography to obtain the target compound Macrocycle-II (4.93 g, yield 22.3percent).

Reference： [1]Patent: KR101847236,2018,B1 .Location in patent: Paragraph 0077-0080; 0097-0100

27
[ 1153-85-1 ]
[ 618442-57-2 ]
[ 1141757-83-6 ]

Yield	Reaction Conditions	Operation in experiment
82%		(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -9-phenylcarbazole,One equivalent (20 g, 40.49 mmol),3-Bromo-9-phenylcarbazole, 2Equivalent (26 g, 81 mmol), 33.5 g of K2CO3, 800 ml of toluene,And 200 ml of water was added to a 2-L 2-neck round bottom flask. The mixture was stirred at room temperature for 30 minutes,Pd (PPh3) 4 (1.4 g, 1.21 mmol) was added and refluxed for 24 hours.After the reaction was completed, the reaction mixture was extracted with methylene chloride, added with MgSO 4 and filtered.After removing the solvent of the obtained organic layer, it was purified by column chromatography to obtain intermediate compound 1 (24.80 g, yield 82%).

Reference： [1]Patent: KR101847236,2018,B1 .Location in patent: Paragraph 0066-0070

28
[ 1153-85-1 ]
[ 618442-57-2 ]
C₅₄H₃₃Br₂N₃ [ No CAS ]

Reference： [1]Patent: KR101847236,2018,B1

29
C₅₄H₃₃Br₂N₃ [ No CAS ]
[ 618442-57-2 ]
C₇₂H₄₄N₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
27%		The compound 2 (15.0 g, 16.98 mmol) obtained above and 3,6-bis (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-phenylcarbazole (8.15 g, 16.98 mmol),14.0 g of anhydrous K2CO3,800 ml of toluene,The mixture was stirred for 30 minutes at room temperature, and then Pd (PPh3) 4 (0.60 g, 0.52 mmol) was added thereto.And the mixture was refluxed for 24 hours.After the reaction was completed, the reaction mixture was extracted with methylene chloride, added with MgSO 4 and filtered.After removing the solvent of the obtained organic layer, the residue was purified by column chromatography to obtain the target compound Macrocycle-I(4.42 g, yield 27percent).

Reference： [1]Patent: KR101847236,2018,B1 .Location in patent: Paragraph 0074-0076

30
3,3'-(5'-bromo-[1,1':3',1''-terphenyl]-4,4''-diyl)bis(pyrimidine-2,4(1H,3H)-dione) [ No CAS ]
[ 618442-57-2 ]
C₇₀H₄₅N₉O₈ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
32%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; at 80℃; for 12h;Inert atmosphere;	To a 500 mL 2-neck flask under a nitrogen atmosphere, add compound 3-5 (1 g, 0.002 mol), compound 3-3 (2.1 g, 0.004 mol), Pd(pph3)4 (0.2 g, 0.0002 mol), Tetrahydrofuran (THF) (100 mL) was added and stirred. Potassium carbonate solution (2N, 100 mL) was added when all the materials in the flask were dissolved. The reaction was conducted by refluxing at 80 C. for 12 hours. After completion of the reaction, the mixture was cooled at room temperature and extracted with ethyl acetate/distilled water to separate the organic layer. After the solvent of the separated organic layer was blown away, purification was performed by column chromatography (methylene chloride:hexane = 1:4 volume ratio) to obtain the final compound of formula (3). Yield and NMR data of the compound of Formula 3 are as follows.Yield: 0.7 g (32%)

Reference： [1]Patent: KR2020/69184,2020,A .Location in patent: Paragraph 0166-0167; 0195-0198

31
[ 22433-90-5 ]
[ 618442-57-2 ]
C₃₄H₁₇N₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
32%	With tetrakis(triphenylphosphine) palladium(0); potassium hydroxide; In tetrahydrofuran; water; for 1h;Reflux;	4.80 g (9.69 mmol) of Intermediate(C), 5.02 g (24.2 mmol) of 2-bromoisophthalonitrile, 4.48 g (3.88 mmol) of tetrakistriphenylphosphine palladium (0) (Pd(PPh3)4), and 8.16 g (145 mmol) of potassium hydroxide were mixed with a mixture solution of 80 mL of THF and 70 mL of water, followed by stirring under reflux for 1 hour. Once the reaction was complete, the reaction mixture was cooled to room temperature, and the reaction mixture was extracted therefrom by ethyl acetate (EA)/water extraction, followed by concentration of the organic layer under reduced pressure. The product was purified using silica gel column chromatography. The product was recrystallized using dichloromethane (DCM)/n-hexane, thereby obtaining a desired compound, 1.54 g of Compound 231 (yield: 32%). LC-Mass (calculated value: 495.15 g/mol, measured value: M+1=496 g/mol)

Reference： [1]Patent: US2020/377490,2020,A1 .Location in patent: Paragraph 0286; 0289-0290

32
[ 2781879-11-4 ]
[ 618442-57-2 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
63%	With tetrakis-(triphenylphosphine)-palladium; potassium carbonate In ethanol; lithium hydroxide monohydrate; toluene at 85℃; for 9h;	2 Preparation of A26: compound 2-2 (990 mg, 2 mmol), compound 1-8 (1.1 g, 4.2 mmol), potassium carbonate (1.1 g, 8 mmol), 20 mL of toluene, 10 mL of absolute ethanol and 6 mL of deionized water to 100 mL Then, tetrakistriphenylphosphine palladium (288 mg, 0.25 mmol) was added to the reaction flask, and the reaction was carried out in an oil bath at 85° C. for 9 h. After the reaction was completed, the reaction system was concentrated and subjected to silica gel column chromatography (eluent: petroleum ether: acetic acid). Ethyl ester = 5:1, v/v) to obtain product A26 in 63% yield.

Reference： [1]Current Patent Assignee: YITAI BEIJING MAT GENOME ENGINEERING INSTITUTE; YITAI HESSEN BIG DATA - CN114605392, 2022, A Location in patent: Paragraph 0092-0093; 0096-0097

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[ 618442-57-2 ] Synthesis Path-Upstream 1~7

[ 618442-57-2 ] Synthesis Path-Downstream 1~32

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Esters

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