[ CAS No. 36848-40-5 ] {[proInfo.proName]}

Name: 36848-40-5|2,7-Dibromophenazine|98%
Brand: Ambeed
SKU: A1156764
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Quality Control of [ 36848-40-5 ]

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Product Details of [ 36848-40-5 ]

CAS No. :	36848-40-5	MDL No. :	MFCD34178727
Formula :	C₁₂H₆Br₂N₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	MILNCXRRKCVYAV-UHFFFAOYSA-N
M.W :	338.00	Pubchem ID :	12560083
Synonyms :

Safety of [ 36848-40-5 ]

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

Application In Synthesis of [ 36848-40-5 ]

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

Downstream synthetic route of [ 36848-40-5 ]

[ 36848-40-5 ] Synthesis Path-Downstream 1~43

1
[ 100398-14-9 ]
[ 36848-40-5 ]

Yield	Reaction Conditions	Operation in experiment
	With lead; iron(II) oxalate

Reference： [1]Vivian [Journal of Organic Chemistry, 1956, vol. 21, p. 824]

2
[ 64168-48-5 ]
[ 36848-40-5 ]
[ 1212-08-4 ]
[ 88046-99-5 ]
[ 88046-98-4 ]

Yield	Reaction Conditions	Operation in experiment
1: 5% 2: 3% 3: 61% 4: 21%	With lead dioxide In benzene Ambient temperature; Further byproducts given;

Reference： [1]Balboni, Claudio; Benati, Luisa; Montevecchi, P. Carlo; Spagnolo, Piero [Journal of the Chemical Society. Perkin transactions I, 1983, p. 2111 - 2117]

3
[ 64168-48-5 ]
[ 36848-40-5 ]
[ 882-33-7 ]

Yield	Reaction Conditions	Operation in experiment
1: 51% 2: 63%	With lead dioxide In acetonitrile Ambient temperature;

Reference： [1]Balboni, Claudio; Benati, Luisa; Montevecchi, P. Carlo; Spagnolo, Piero [Journal of the Chemical Society. Perkin transactions I, 1983, p. 2111 - 2117]

4
[ 64168-48-5 ]
[ 36848-40-5 ]
[ 1212-08-4 ]
[ 88046-99-5 ]
[ 88046-98-4 ]
[ 882-33-7 ]

Yield	Reaction Conditions	Operation in experiment
1: 5% 2: 3% 3: 61% 4: 28% 5: 21%	With lead dioxide In benzene Ambient temperature; effect of substituents and solvents on the reactivity of 4'-substituted benzenesulphenanilides;

Reference： [1]Balboni, Claudio; Benati, Luisa; Montevecchi, P. Carlo; Spagnolo, Piero [Journal of the Chemical Society. Perkin transactions I, 1983, p. 2111 - 2117]

5
[ 64168-48-5 ]
[ 36848-40-5 ]
[ 88046-99-5 ]
[ 88046-98-4 ]
[ 882-33-7 ]

Yield	Reaction Conditions	Operation in experiment
1: 1.5% 2: 17% 3: 2% 4: 90%	With silver(l) oxide In benzene Ambient temperature;

Reference： [1]Balboni, Claudio; Benati, Luisa; Montevecchi, P. Carlo; Spagnolo, Piero [Journal of the Chemical Society. Perkin transactions I, 1983, p. 2111 - 2117]

Yield	Reaction Conditions	Operation in experiment
	/BRN= 805551/ (3e), PbO2;
	p-Bromoanilin, p-Bromonitrobenzol, KOH;

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; tin(ll) chloride

9
[ 106-40-1 ]
[ 36848-40-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 2: 5 percent / lead dioxide / benzene / Ambient temperature
	Multi-step reaction with 2 steps 2: 63 percent / lead dioxide / acetonitrile / Ambient temperature
	Multi-step reaction with 2 steps 2: 2 percent / silver(I) oxide / benzene / Ambient temperature

Reference： [1]Balboni, Claudio; Benati, Luisa; Montevecchi, P. Carlo; Spagnolo, Piero [Journal of the Chemical Society. Perkin transactions I, 1983, p. 2111 - 2117]
[2]Balboni, Claudio; Benati, Luisa; Montevecchi, P. Carlo; Spagnolo, Piero [Journal of the Chemical Society. Perkin transactions I, 1983, p. 2111 - 2117]
[3]Balboni, Claudio; Benati, Luisa; Montevecchi, P. Carlo; Spagnolo, Piero [Journal of the Chemical Society. Perkin transactions I, 1983, p. 2111 - 2117]

10
[ 3460-18-2 ]
[ 36848-40-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 2: iron (II)-oxalate; lead

Reference： [1]Vivian [Journal of Organic Chemistry, 1956, vol. 21, p. 824]

11
[ 6358-77-6 ]
[ 36848-40-5 ]

Reference： [1]Journal of Organic Chemistry,1956,vol. 21,p. 824

12
[ 36848-40-5 ]
[ 97674-02-7 ]
[ 1246661-74-4 ]

Yield	Reaction Conditions	Operation in experiment
88%	In 1,4-dioxane at 100℃; for 4h; Inert atmosphere;	13; 26.3 To a solution of 2,7-dibromophenazine (13-2) (1.52 g, 4.50 mmol) in dry dioxane (75 mL) under N2 was added tributyl(l-ethoxyvinyl)stannane (3.34 ml, 9.89 mmol) and Pd(dppf)Cl2 (0.316 g, 0.450 mmol). The resultant mixture was heated at 1000C for 4h in a sealed tube. The crude reaction mixture was filtered through CELITE545, and the volatiles were removed in vacuo. The crude brown solid was triturated with isohexanes and filtered to give 2,7-bis(l-ethoxyvinyl)phenazine as a brown solid (1.27 g, 88 % yield). 1H NMR (CDCl3) δ 8.55-8.53 (2H, m), 8.19-8.15 (2H, m), 8.11-8.07 (2H, m), 4.98 (2H, d, J = 3 Hz), 4.49 (2H, d, J = 3 Hz), 4.03 (4H, q, J = 7 Hz), 1.50 (6H, t, J = 7 Hz) ppm. LC-MS (ESI): m/z 322.1 (M+H)+.

Reference： [1]Current Patent Assignee: PRESIDIO PHARMACEUTICALS, INC.; PRESEDIO PHARMACEUTICALS - WO2010/111534, 2010, A1 Location in patent: Page/Page column 121-122

13
[ 70339-90-1 ]
[ 36848-40-5 ]

Yield	Reaction Conditions	Operation in experiment
16%	With acetic acid for 1.5h; Reflux;	13; 26.2 5-bromo-N-(4-bromophenyl)-2-nitrosoaniline 513-1) (10 g, 28.1 mmol) in AcOH (300 mL) was heated under reflux for 1.5 h. Water (400 mL) was then added and the brown precipitate formed was collected by filtration after washing with water (2 x 200 mL). The product was purified by silica gel chromatography (SiO2, hexanes/DCM = 1/1 (v/v)) to afford a brown solid, 2,7-dibromophenazine 13-2 (1.52 g, 16 % yield).1H NMR (CDCl3) δ 8.43 (2H, dd, J2.2, 0.4 Hz), 8.10 (2H, dd, J9.2, 0.4 Hz), 7.91 (2H, dd, J 9.2, 2.2 Hz) ppm. LC-MS (ESI): m/z 338.6 (M+H)+.

Reference： [1]Current Patent Assignee: PRESIDIO PHARMACEUTICALS, INC.; PRESEDIO PHARMACEUTICALS - WO2010/111534, 2010, A1 Location in patent: Page/Page column 121-122

14
[ 36848-40-5 ]
C₂₆H₂₆N₈ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,4-dioxane / 15 h / 110 °C 2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / tetrahydrofuran; water / 15 h / Reflux 3: hydrogenchloride / water; methanol / 0.5 h

Reference： [1]Yu, Wensheng; Coburn, Craig A.; Yang, De-Yi; Meinke, Peter T.; Wong, Michael; Rosenblum, Stuart B.; Chen, Kevin X.; Njoroge, George F.; Chen, Lei; Dwyer, Michael P.; Jiang, Yueheng; Nair, Anilkumar G.; Selyutin, Oleg; Tong, Ling; Zeng, Qingbei; Zhong, Bin; Ji, Tao; Hu, Bin; Agrawal, Sony; Xia, Ellen; Zhai, Ying; Liu, Rong; Kong, Rong; Ingravallo, Paul; Asante-Appiah, Ernest; Nomeir, Amin; Fells, James; Kozlowski, Joseph A. [Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 13, p. 3158 - 3162]

15
[ 36848-40-5 ]
[ 1246660-07-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,4-dioxane / 15 h / 110 °C 2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / tetrahydrofuran; water / 15 h / Reflux 3: hydrogenchloride / water; methanol / 0.5 h 4: (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 10 h

16
[ 36848-40-5 ]
[ 73183-34-3 ]
C₂₄H₃₀B₂N₂O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 110℃; for 15h;

17
[ 36848-40-5 ]
C₂₈H₂₄N₂O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: potassium carbonate / dimethyl sulfoxide / 8 h / 110 °C / Inert atmosphere 2: palladium diacetate; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate / toluene; 1,4-dioxane / 15 h / 110 °C / Inert atmosphere

Reference： [1]Current Patent Assignee: CANON INC. - US2017/313934, 2017, A1

18
[ 36848-40-5 ]
C₃₄H₃₈N₂O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: potassium carbonate / dimethyl sulfoxide / 8 h / 110 °C / Inert atmosphere 2: palladium diacetate; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate / toluene; 1,4-dioxane / 15 h / 110 °C / Inert atmosphere 3: sodium dithionite; potassium carbonate / acetonitrile; water / 10 h / 90 °C / Inert atmosphere

Reference： [1]Current Patent Assignee: CANON INC. - US2017/313934, 2017, A1

19
[ 36848-40-5 ]
[ 108-95-2 ]
C₁₈H₁₁BrN₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
32%	With potassium carbonate In dimethyl sulfoxide at 110℃; for 8h; Inert atmosphere;	2 The example compound B-18 can be synthesized, for example, by the following procedure. First, a compound XX-3 is synthesized. In a 100-ml reaction chamber, 500 mg (1.48 mmol) of the compound XX-1 and 278 mg (2.96 mmol) of phenol were mixed together in dimethyl sulfoxide (DMSO) (5 ml), and dissolved oxygen was removed toy nitrogen. Next, 62.8 mg (0.074 mmol) of a CuI/Sparteine complex and 409 mg (2.96 mmol) of potassium carbonate were added in a nitrogen atmosphere, and a reaction was performed by heating and refluxing at 110° C. for 8 hours.After the reaction solution was cooled to room temperature and was then condensed at a reduced pressure, separation and purification were performed by a silica gel chromatography (mobile phase: hexane/chloroform), so that a yellow solid compound XX-3 was obtained (160 mg, yield: 32%).

Reference： [1]Current Patent Assignee: CANON INC. - US2017/313934, 2017, A1 Location in patent: Paragraph 0206-0208

20
[ 36848-40-5 ]
[ 5720-06-9 ]
C₂₆H₂₀N₂O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
45%	With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate In 1,4-dioxane; toluene at 100℃; for 6h; Inert atmosphere;	6 The example compound A-3 can be synthesized, for example, by the following procedure. First, a compound XX-5 is synthesized. In a 50-ml reaction chamber, 507 mg (1.5 mmol) of the compound XX-1 and 638 mg (4.5 mmol) of 2-methoxyphenylboronic acid were mixed in a mixed solvent of toluene/1,4-dioxane (6 ml/6 ml), and dissolved oxygen was removed by nitrogen. Next, 13.5 mg (0.06 mmol) of Pd(OAc)2, 61.6 mg (0.15 mmol) of 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (S-Phos), and 1.72 g (7.5 mmol) of tripotassium phosphate were added in a nitrogen atmosphere, and a reaction was performed by heating and refluxing at 100° C. for 6 hours.After the reaction solution was cooled to room temperature, a powder precipitated by reduced-pressure condensation was purified by recrystallization, so that a yellow solid compound XX-5 was obtained (265 mg, yield: 45%).

Reference： [1]Current Patent Assignee: CANON INC. - US2017/313934, 2017, A1 Location in patent: Paragraph 0230-0232

21
[ 36848-40-5 ]
[ 5720-06-9 ]
C₃₂H₃₄N₂O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: palladium diacetate; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate / toluene; 1,4-dioxane / 6 h / 100 °C / Inert atmosphere 2: sodium dithionite; potassium carbonate / acetonitrile / 9 h / 90 °C / Inert atmosphere

Reference： [1]Current Patent Assignee: CANON INC. - US2017/313934, 2017, A1

22
[ 36848-40-5 ]
2,6-diphenoxyphenylboronic acid [ No CAS ]
C₄₈H₃₂N₂O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62%	With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate In 1,4-dioxane; toluene at 100℃; for 4h; Inert atmosphere;	7 The example compound A-25 can be synthesized, for example, by the following procedure. First, a compound XX-6 is synthesized. In a 50-ml reaction chamber, 507 mg (1.5 mmol) of the compound XX-1 and 1.38 g (4.5 mmol) of 2,6-diphenoxyphenylboronic acid were mixed in a mixed solvent of toluene/1,4-dioxane (6 ml/6 ml), and dissolved oxygen was removed by nitrogen. Next, 13.5 mg (0.06 mmol) of Pd(OAc)2, 61.6 mg (0.15 mmol) of 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (S-Phos), and 1.72 g (7.5 mmol) of tripotassium phosphate were added in a nitrogen atmosphere, and a reaction was performed by heating and refluxing at 100° C. for 4 hours.After the reaction solution was cooled to room temperature, a powder precipitated by reduced-pressure condensation was purified by recrystallization, so that a yellow solid compound XX-6 was obtained (650 mg, yield: 62%).

Reference： [1]Current Patent Assignee: CANON INC. - US2017/313934, 2017, A1 Location in patent: Paragraph 0237-0239

23
[ 36848-40-5 ]
[ 208399-66-0 ]
C₂₈H₂₄N₂O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate In 1,4-dioxane; toluene at 100℃; for 6h; Inert atmosphere;	12 The example compound F-2 can be synthesized, for example, by the following procedure. First, a compound XX-9 is synthesized. In a 50-ml reaction chamber, 507 mg (1.50 mmol) of a compound XX-1 and 747 mg (4.5 mmol) of 4-metoxy-2-methylphenylboronic acid were mixed in a mixed solvent of toluene/1,4-dioxane (7 ml/7 ml), and dissolved oxygen was removed by nitrogen. Next, 13.5 mg (0.06 mmol) of Fd(OAc)2, 61.6 mg (0.15 mmol) of 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (S-Phos), and 1.72 g (7.5 mmol) of tripotassium phosphate were added in a nitrogen atmosphere, and a reaction was performed by heating and refluxing at 100° C. for 6 hours.After the reaction solution was cooled to room temperature and was then condensed at a reduce pressure, separation and purification were performed by a silica gel chromatography (mobile phase: hexane/chloroform), so that a yellow solid compound XX-9 was obtained (478 mg, yield: 76%).

Reference： [1]Current Patent Assignee: CANON INC. - US2017/313934, 2017, A1 Location in patent: Paragraph 0268-0270

24
[ 36848-40-5 ]
[ 208399-66-0 ]
C₃₄H₃₈N₂O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: palladium diacetate; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate / toluene; 1,4-dioxane / 6 h / 100 °C / Inert atmosphere 2: sodium dithionite; potassium carbonate / acetonitrile; water / 9 h / 90 °C / Inert atmosphere

Reference： [1]Current Patent Assignee: CANON INC. - US2017/313934, 2017, A1

25
[ 36848-40-5 ]
[ 870778-88-4 ]
C₃₂H₃₂N₂O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate In 1,4-dioxane; toluene at 110℃; for 8h; Inert atmosphere;	1 The example compound A-21 can be synthesized, for example, by the following procedure. First, a compound XX-2 is synthesized. In a 50-ml reaction chamber, 676 mg (2.0 mmol) of a compound XX-1 and 1.26 g (6.0 mmol) of 2-isopropoxy-6-methoxyphenylboronic acid were mixed together in a mixed solvent of toluene/1,4-dioxane (7 ml/7 ml), and dissolved oxygen was removed by nitrogen. In addition, the compound XX-1 was a compound synthesized in accordance with Tetrahedron Letters, 52, 6484 (2011).Next, 18.0 mg (0.08 mmol) of Pd(OAc)2, 82.1 mg (0.10 mmol) of 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (S-Phos), and 2.30 g (10.0 mmol) of tripotassium phosphate were added in a nitrogen atmosphere, and a reaction was performed by heating and refluxing at 110° C. for 8 hours.After the reaction solution was cooled to room temperature and was then condensed at a reduced pressure, separation and purification were performed by a silica gel chromatography (mobile phase: hexane/chloroform), so that a yellow solid compound XX-2 was obtained (770 mg, yield: 75%).

Reference： [1]Current Patent Assignee: CANON INC. - US2017/313934, 2017, A1 Location in patent: Paragraph 0198-0201

26
[ 36848-40-5 ]
[ 870778-88-4 ]
C₃₈H₄₆N₂O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: palladium diacetate; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate / toluene; 1,4-dioxane / 8 h / 110 °C / Inert atmosphere 2: sodium dithionite; potassium carbonate / acetonitrile; water / 9 h / 90 °C / Inert atmosphere

Reference： [1]Current Patent Assignee: CANON INC. - US2017/313934, 2017, A1

27
[ 90965-63-2 ]
[ 1575-37-7 ]
[ 36848-40-5 ]
[ 105836-93-9 ]

Yield	Reaction Conditions	Operation in experiment
	With sulfuric acid In ethanol at 65℃; for 4h; Overall yield = 82.4 %; Overall yield = 5.82 g;	1 Example 1 Synthesis of dibromophenazine To 250 ml three-necked flask was added 4-bromo o-phenylenediamine 3.91 g (molecular weight 186, 0.021 mol)4-bromo-o-benzoquinone 3.91 g (molecular weight 186,0.021mol),Ethanol (40 ml),Under stirring,3 minutes 0.2 g concentrated sulfuric acid (concentration 98%),The reaction was carried out at 65 ° C for 4 hours,After the reaction,Cool to room temperature,filter,Washed,drying,Column chromatography,Ethyl acetate / petroleum ether rinse,Almost equal amounts of 2,7-dibromophenazine and 2,8-dibromophenazine were obtained,Total 5.82 grams (molecular weight 336),The total yield of 82.4%.

Reference： [1]Current Patent Assignee: BEIJING ETERNAL MATERIAL TECHNOLOGY CO LTD - CN106554322, 2017, A Location in patent: Paragraph 0049; 0050; 0051

28
N-4-bromophenyl-2-nitroso-5-bromoaniline [ No CAS ]
[ 36848-40-5 ]

Yield	Reaction Conditions	Operation in experiment
90%	With BSA In acetonitrile at 100℃; for 16h; Sealed tube;	1 Embodiment 1, the synthetic process of phenazine base compound Put 1mmol of p-bromonitrobenzene and 1mmol of p-bromoaniline into a single-necked bottle, add an appropriate amount of potassium tert-butoxide and tetrahydrofuran, and react at -78 degrees Celsius for 1 hour to obtain a tan intermediate product. After filtering, the tan intermediate is obtained. Put it into a high-pressure reaction cylinder, add 15 mL of acetonitrile as a solvent, add 6 mL of BSA as a ring-closing agent, seal the cylinder, react at 100 degrees Celsius for 16 hours, filter out bright yellow fractions, and obtain 2,6-dibromophenazine with a yield of about 90%.
68%	With N,O-bis-(trimethylsilyl)-acetamide In acetonitrile at 100℃; for 12h; Inert atmosphere; Sealed tube;
3.4 g	With N,O-bis-(trimethylsilyl)-acetamide In acetonitrile at 100℃; for 16h; Inert atmosphere; Sealed tube;

With N,O-bis-(trimethylsilyl)-acetamide In acetonitrile at 100℃; for 12h; Sealed tube;

In the second step, N-aryl-2-nitrosoanilines is cyclized as follows. N, O bis(trimethylsilypacetamide (BSA) (1.2 mL, 5 mmol) was added to a solution of nitrosoaniline (1 mmol) in MeCN (4 mL) to form a reaction mixture. The reaction mixture was added into a sealed tube. The sealed tube was then heated to 100° C. for 12 hours. The reaction mixture was filtered to obtain a precipitate, and the precipitate was washed with cold MeOH, then dried under vacuum to obtain the main body of the phenazine group of the organic electroluminescent compound represented by Formula (I).

Reference： [1]Current Patent Assignee: SHANGHAI JIAO TONG UNIVERSITY - CN113801102, 2021, A Location in patent: Paragraph 0036-0038
[2]Teo, Yew Chin; Jin, Zexin; Xia, Yan [Organic Letters, 2018, vol. 20, # 11, p. 3300 - 3304]
[3]Vitaku, Edon; Gannett, Cara N.; Carpenter, Keith L.; Shen, Luxi; Abruña, Héctor D.; Dichtel, William R. [Journal of the American Chemical Society, 2020, vol. 142, # 1, p. 16 - 20]
[4]Current Patent Assignee: INT TECH CO., LTD. - US2020/207752, 2020, A1 Location in patent: Paragraph 0051

29
[ 106-40-1 ]
[ 36848-40-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: potassium-t-butoxide / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere 2: N,O-bis-(trimethylsilyl)-acetamide / acetonitrile / 12 h / 100 °C / Inert atmosphere; Sealed tube
	Multi-step reaction with 2 steps 1: potassium-t-butoxide / tetrahydrofuran / -78 °C / Inert atmosphere 2: N,O-bis-(trimethylsilyl)-acetamide / acetonitrile / 16 h / 100 °C / Inert atmosphere; Sealed tube
	Multi-step reaction with 2 steps 1: potassium-t-butoxide / tetrahydrofuran / 1 h / -78 °C 2: N,O-bis-(trimethylsilyl)-acetamide / acetonitrile / 12 h / 100 °C / Sealed tube

Multi-step reaction with 2 steps 1: potassium-t-butoxide / tetrahydrofuran / 1 h / -78 °C 2: BSA / acetonitrile / 16 h / 100 °C / Sealed tube

Reference： [1]Teo, Yew Chin; Jin, Zexin; Xia, Yan [Organic Letters, 2018, vol. 20, # 11, p. 3300 - 3304]
[2]Vitaku, Edon; Gannett, Cara N.; Carpenter, Keith L.; Shen, Luxi; Abruña, Héctor D.; Dichtel, William R. [Journal of the American Chemical Society, 2020, vol. 142, # 1, p. 16 - 20]
[3]Current Patent Assignee: INT TECH CO., LTD. - US2020/207752, 2020, A1
[4]Current Patent Assignee: SHANGHAI JIAO TONG UNIVERSITY - CN113801102, 2021, A

30
[ 586-78-7 ]
[ 36848-40-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: potassium-t-butoxide / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere 2: N,O-bis-(trimethylsilyl)-acetamide / acetonitrile / 12 h / 100 °C / Inert atmosphere; Sealed tube
	Multi-step reaction with 2 steps 1: potassium-t-butoxide / tetrahydrofuran / -78 °C / Inert atmosphere 2: N,O-bis-(trimethylsilyl)-acetamide / acetonitrile / 16 h / 100 °C / Inert atmosphere; Sealed tube
	Multi-step reaction with 2 steps 1: potassium-t-butoxide / tetrahydrofuran / 1 h / -78 °C 2: N,O-bis-(trimethylsilyl)-acetamide / acetonitrile / 12 h / 100 °C / Sealed tube

Multi-step reaction with 2 steps 1: potassium-t-butoxide / tetrahydrofuran / 1 h / -78 °C 2: BSA / acetonitrile / 16 h / 100 °C / Sealed tube

31
[ 36848-40-5 ]
C₆₈H₅₆N₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: johnphos; caesium carbonate; palladium diacetate / 1,4-dioxane / 24.08 h / 20 - 150 °C / Inert atmosphere; Sealed tube 2: hydrogenchloride / chloroform; isopropyl alcohol; water / 24 h / 80 °C / Inert atmosphere

Reference： [1]Teo, Yew Chin; Jin, Zexin; Xia, Yan [Organic Letters, 2018, vol. 20, # 11, p. 3300 - 3304]

32
[ 36848-40-5 ]
6,7-bis(2,6-dimethylphenyl)-1,4-dimethyl-1,4-dihydro-1,4-epoxynaphthalene [ No CAS ]
C₆₈H₆₀N₂O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
55%	With palladium diacetate; caesium carbonate; johnphos In 1,4-dioxane at 20 - 150℃; for 24.0833h; Inert atmosphere; Sealed tube;

Reference： [1]Teo, Yew Chin; Jin, Zexin; Xia, Yan [Organic Letters, 2018, vol. 20, # 11, p. 3300 - 3304]

33
[ 1013-88-3 ]
[ 36848-40-5 ]
C₃₈H₂₆N₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In toluene for 16h; Inert atmosphere; Reflux;

Reference： [1]Vitaku, Edon; Gannett, Cara N.; Carpenter, Keith L.; Shen, Luxi; Abruña, Héctor D.; Dichtel, William R. [Journal of the American Chemical Society, 2020, vol. 142, # 1, p. 16 - 20]

34
[ 36848-40-5 ]
[ 92-84-2 ]
C₃₆H₂₂N₄S₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With copper; potassium carbonate In 1,2-dichloro-benzene at 190℃; for 24h; Inert atmosphere;	Dibromophenazine (1 mmol), nitrogen donor (2 mmol), copper powder (4 mmol) and K2CO3 (5 mmol) were added in a flask. Dichlorobenzene (5 mL) was further added into the flask under nitrogen atmosphere and the flask was heated to 190° C. in an oil bath for 24 hours to obtain a reaction mixture. The reaction mixture was filtered to obtain a solution. The organic solvent of the solution was removed under vacuum to obtain a residue. The residue was purified by silica gel chromatography to obtain the organic electroluminescent compound represented by Formula (II).

Reference： [1]Current Patent Assignee: INT TECH CO., LTD. - US2020/207752, 2020, A1 Location in patent: Paragraph 0053

35
[ 36848-40-5 ]
[ 56-40-6 ]
C₁₆H₁₄N₄O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; dicyclohexyl(2′,4′,6′-tri-isopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphane; potassium-t-butoxide In <i>tert</i>-butyl alcohol at 100℃; for 16h; Sealed tube;
92%	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; potassium-t-butoxide; BrettPhos In <i>tert</i>-butyl alcohol at 100℃; for 12h; Inert atmosphere; Sealed tube;	1 Example 1-9 Synthesis of phenazine amino acid derivatives Under nitrogen atmosphere,Weigh 2,7-dibromophenazine (3mmol, 1.014g), glycine (7.2mmol, 0.54g), Pd2(dba)3 (5mol%, 137.4mg),BrettPhos (10mol%, 161mg), potassium tert-butoxide (15mmol, 1.68g),30 mL of tert-butanol was placed in a thick-walled pressure-resistant reaction tube.Stir well and raise the temperature to 100°C,After 12 h of reaction, it was cooled to room temperature.filter and collect the filter cake,The filter cake was dissolved in deionized water and filtered again to remove water-insoluble impurities.Collect the filtrate,The filtrate was acidified with HCl to pH=34,After the solid is separated out, filter, collect the filter cake,The filter cake was washed with deionized water (2×5 mL), and the target compound 3 was obtained after drying.further,Purified by reversed-phase column (C18) (MeOH:H2O=15:85), the yield was 92%.

Reference： [1]Pang, Shuai; Wang, Xinyi; Wang, Pan; Ji, Yunlong [Angewandte Chemie - International Edition, 2021, vol. 60, # 10, p. 5289 - 5298][Angew. Chem., 2021, vol. 133, # 10, p. 5349 - 5358,10]
[2]Current Patent Assignee: WESTLAKE UNIV; UNIV WESTLAKE - CN114105893, 2022, A Location in patent: Paragraph 0130-0132

36
[ 36848-40-5 ]
[ 107-95-9 ]
C₁₈H₁₈N₄O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
99%	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; dicyclohexyl-(2′,4′,6′-triisopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine; potassium <i>tert</i>-butylate In <i>tert</i>-butyl alcohol at 100℃; for 16h; Sealed tube;

37
[ 36848-40-5 ]
[ 56-12-2 ]
C₂₀H₂₂N₄O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; dicyclohexyl-(2′,4′,6′-triisopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine; potassium <i>tert</i>-butylate In <i>tert</i>-butyl alcohol at 100℃; for 16h; Sealed tube;

38
[ 36848-40-5 ]
[ 302-72-7 ]
C₁₈H₁₈N₄O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; dicyclohexyl-(2′,4′,6′-triisopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine; potassium <i>tert</i>-butylate In <i>tert</i>-butyl alcohol at 100℃; for 16h; Sealed tube;

39
[ 36848-40-5 ]
[ 1692-15-5 ]
C₂₂H₁₄N₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
56.9%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In 1,4-dioxane; water at 85℃; for 72h;

Reference： [1]Cui, Zheng; Gao, Xiang; Jin, Guo-Xin; Lin, Yue-Jian; Liu, Dong; Shen, Yue-Rong [Journal of the American Chemical Society, 2021, vol. 143, # 42, p. 17833 - 17842]

40
[ 36848-40-5 ]
[ 1692-25-7 ]
C₂₂H₁₄N₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
59.9%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In 1,4-dioxane; water at 85℃; for 72h;

Reference： [1]Cui, Zheng; Gao, Xiang; Jin, Guo-Xin; Lin, Yue-Jian; Liu, Dong; Shen, Yue-Rong [Journal of the American Chemical Society, 2021, vol. 143, # 42, p. 17833 - 17842]

41
[ 36848-40-5 ]
[ 111-94-4 ]
C₂₄H₂₂N₈ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; BrettPhos; Cs₂CO₃ In <i>tert</i>-butyl alcohol at 100℃; for 12h; Inert atmosphere;	10 Under nitrogen atmosphere,Weigh 2,7-dibromophenazine (3mmol, 1.014g),3,3'-iminodipropionitrile (12mmol, 1.48g),Pd2(dba)3 (5mol%, 137.4mg),BrettPhos (10mol%, 161mg),Cesium carbonate (21mmol, 6.842g), tert-butanol 10mL,in the reaction tube.Fully stirred and heated to 100 , reacted for 12h and filtered while hot.The solid was washed with deionized water and EtOH successively and then dried in a vacuum drying oven.Compound 18 was obtained.Weigh compound 18 (1 mmol, 422 mg) into a thick-walled pressure bottle, add NaOH (4 mmol, 160 mg), 4 mL of deionized water, fully stir and heat up to 150 ° C, react for 12 h after cooling and filtration,Collect solids.further,Purified by reverse phase column (C18) (MeOH:H2O=5:95),Compound 19 was obtained.Yield 90%.

Reference： [1]Current Patent Assignee: WESTLAKE UNIV; UNIV WESTLAKE - CN114105893, 2022, A Location in patent: Paragraph 0136-0139

42
[ 36848-40-5 ]
[ 111-94-4 ]
C₂₄H₂₆N₄O₈ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; BrettPhos; Cs₂CO₃ / <i>tert</i>-butyl alcohol / 12 h / 100 °C / Inert atmosphere 2: water monomer / 12 h / 150 °C / Sealed tube; Alkaline conditions

Reference： [1]Current Patent Assignee: WESTLAKE UNIV; UNIV WESTLAKE - CN114105893, 2022, A

43
[ 36848-40-5 ]
[ 86-74-8 ]
C₃₆H₂₂N₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With copper oxide (I); potassium carbonate In N,N-dimethyl-formamide at 135℃; for 24h;	1 Put 1 g (3 mmol) of 2,6-dibromophenazine into a three-necked flask, add 0.1 g of cuprous oxide, add 6 mmol of a donor group (the donor group is carbazole, tert-butylcarbazole, diphenylamine) , triphenylamine, phenoxazine, tert-butyl diphenylamine, phenylcarbazole), 3 g of potassium carbonate and 20 mL of DMF were used as solvents. The reaction was carried out at 135 degrees Celsius for 24 hours to obtain the final product. The NMR of the final product was

Reference： [1]Current Patent Assignee: SHANGHAI JIAO TONG UNIVERSITY - CN113801102, 2021, A Location in patent: Paragraph 0013; 0036; 0039-0041

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