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Chemistry
Heterocyclic Building Blocks
Tetrahydropyrans
9,10-Dibromo-2-methylanthracene
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[ CAS No. 177839-45-1 ] {[proInfo.proName]}

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Chemical Structure| 177839-45-1
Chemical Structure| 177839-45-1
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Product Details of [ 177839-45-1 ]

CAS No. :177839-45-1 MDL No. :MFCD00266492
Formula : C15H10Br2 Boiling Point : -
Linear Structure Formula :- InChI Key :PNDNWMMKRSTYTC-UHFFFAOYSA-N
M.W : 350.05 Pubchem ID :1713096
Synonyms :

Safety of [ 177839-45-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 177839-45-1 ]

* 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 [ 177839-45-1 ]

[ 177839-45-1 ] Synthesis Path-Downstream   1~42

  • 1
  • [ 613-12-7 ]
  • [ 177839-45-1 ]
YieldReaction ConditionsOperation in experiment
90% With N-Bromosuccinimide; trifluoroacetic acid; In chloroform; at 20℃;Inert atmosphere; Schlenk technique; To a 250mL round bottom flask, the compound MA (1.00g, 5.20mmol), n-bromosuccinimide (NBS) (2.23g, 12.00mmol) and 200μL trifluoroacetic acid was dissolved in 20mL chloroform. The solution was stirred overnight at room temperature. After reaction, most of chloroform was evaporated, methanol was then added, a yellow needle-like crystal was obtained (90% yield). 1H NMR (400MHz, CDCl3): δ (ppm) 8.58-8.54 (m, 2H), 8.48 (d, J=9.22Hz, 1H), 8.34 (s, 1H), 7.64-7.58 (m, 2H), 7.46 (dd, J1=1.52Hz, J2=8.96Hz, 1H), 2.63 (d, J=0.72Hz, 3H). 13C NMR (100MHz, CDCl3): δ (ppm) 137.39, 131.04, 130.99, 130.40, 130.11, 129.61, 128.17, 128.07, 128.03, 127.22, 126.89, 126.34, 123.32, 122.34, 22.04. MS (MALDI-TOF) m/z=349.9127 (M+)
Reference： [1]Dyes and Pigments,2013,vol. 99,p. 105 - 115
[2]Chemische Berichte,1874,vol. 7,p. 1193
    Journal fuer Praktische Chemie (Leipzig),1909,vol. <2> 79,p. 557
  • 2
  • [ 177839-45-1 ]
  • [ 117-78-2 ]
Reference： [1]Journal fur praktische Chemie (Leipzig 1954),1915,vol. <2> 92,p. 51
  • 3
  • [ 177839-45-1 ]
  • 10-bromo-3-methyl-anthracene-9-carboxylic acid [ No CAS ]
Reference： [1]Zhurnal Obshchei Khimii,1953,vol. 23,p. 130,133, engl. Ausg. S. 127, 129
  • 4
  • [ 177839-45-1 ]
  • [ 544-92-3 ]
  • 2-methyl-9,10-dicyanoanthracene [ No CAS ]
Reference： [1]Journal of the Chemical Society. Perkin transactions II,1996,p. 1005 - 1010
  • 5
  • [ 64-17-5 ]
  • [ 177839-45-1 ]
  • [ 7697-37-2 ]
  • [ 84-54-8 ]
Reference： [1]Journal fur praktische Chemie (Leipzig 1954),1909,vol. <2> 79,p. 558
    Chemische Berichte,1874,vol. 7,p. 1196
  • 6
  • [ 177839-45-1 ]
  • [ 64-19-7 ]
  • chromic acid [ No CAS ]
  • [ 117-78-2 ]
Reference： [1]Journal fur praktische Chemie (Leipzig 1954),1915,vol. <2> 92,p. 51
  • 9
  • [ 177839-45-1 ]
  • [ 177839-46-2 ]
Reference： [1]Journal of the Chemical Society. Perkin transactions II,1996,p. 1005 - 1010
  • 10
  • [ 108-88-3 ]
  • [ 177839-45-1 ]
Reference： [1]Chemische Berichte,1874,vol. 7,p. 1193
    Journal fuer Praktische Chemie (Leipzig),1909,vol. <2> 79,p. 557
  • 11
  • [ 108847-20-7 ]
  • [ 177839-45-1 ]
  • 2-methyl-9,10-bis(dibenzothiophen-4-yl)anthracene [ No CAS ]
Reference： [1]Organic electronics,2011,vol. 12,p. 595 - 601
  • 12
  • [ 84-54-8 ]
  • [ 177839-45-1 ]
Reference： [1]Dyes and Pigments,2013,vol. 99,p. 105 - 115
  • 13
  • [ 177839-45-1 ]
  • 2-(bromomethyl)-9,10-di(2-naphthalenyl)anthracene [ No CAS ]
Reference： [1]Dyes and Pigments,2013,vol. 99,p. 105 - 115
  • 14
  • [ 177839-45-1 ]
  • 9,10-di(naphthalen-2-yl)anthracene-2-carbaldehyde [ No CAS ]
Reference： [1]Dyes and Pigments,2013,vol. 99,p. 105 - 115
  • 15
  • [ 177839-45-1 ]
  • 9,10-di(3-quinolinyl)anthracene-2-carbaldehyde [ No CAS ]
Reference： [1]Dyes and Pigments,2013,vol. 99,p. 105 - 115
  • 16
  • [ 177839-45-1 ]
  • 9,10-di(3-quinolinyl)-2-vinylanthracene [ No CAS ]
Reference： [1]Dyes and Pigments,2013,vol. 99,p. 105 - 115
  • 17
  • [ 177839-45-1 ]
  • 9,10-di(naphthalen-2-yl)-2-vinylanthracene [ No CAS ]
Reference： [1]Dyes and Pigments,2013,vol. 99,p. 105 - 115
  • 18
  • [ 32316-92-0 ]
  • [ 177839-45-1 ]
  • [ 804560-00-7 ]
YieldReaction ConditionsOperation in experiment
80% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran;Inert atmosphere; Schlenk technique; Reflux; 2MADN was synthesized by the Suzuki cross-coupling reaction. A two-necked flask containing the compound MADBr (1.00g, 2.85mmol), 2NB (1.70g, 9.99mmol), tetrakis(triphenylphosphine)palladium(0) (300mg, 2.60mmol), and 2M K2CO3 (3mL) and THF (40mL) was equipped with a magnetic stirrer and a reflux condenser was heated to reflux overnight under a N2 purge. The mixture was then poured into water and extracted with 50mL dichloromethane (DCM). The combined organic layer was dried with anhydrous MgSO4 and evaporated to dryness. The crude product was purified by silica-gel column chromatography using hexane as eluent affording the title compound as a pale yellow solid (80% yield). 1H NMR (400MHz, CDCl3): δ (ppm) 8.12-8.01 (m, 6H), 7.97-7.95 (m, 2H), 7.75-7.61 (m, 9H), 7.49 (s, 1H), 7.31-7.26 (m, 2H), 7.17 (d, J=8.8Hz, 1H), 2.36 (s, 3H). 13C NMR (100MHz, CDCl3): δ (ppm) 136.74, 136.01, 134.90, 133.50, 133.44, 132.78, 130.30, 130.24, 129.73, 129.63, 129.60, 128.74, 128.20, 128.14, 128.03, 127.97, 127.96, 127.94, 127.08, 126.99, 126.97, 126.45, 126.40, 126.23, 126.20, 125.16, 125.07, 124.76, 22.02. MS (MALDI-TOF) m/z=444.1912 (M+).
Reference： [1]Dyes and Pigments,2013,vol. 99,p. 105 - 115
  • 19
  • [ 177839-45-1 ]
  • [ 191162-39-7 ]
  • 2-methyl-9,10-di(3-quinolinyl)anthracene [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran;Inert atmosphere; Schlenk technique; Reflux; General procedure: 2MADN was synthesized by the Suzuki cross-coupling reaction. A two-necked flask containing the compound MADBr (1.00g, 2.85mmol), 2NB (1.70g, 9.99mmol), tetrakis(triphenylphosphine)palladium(0) (300mg, 2.60mmol), and 2M K2CO3 (3mL) and THF (40mL) was equipped with a magnetic stirrer and a reflux condenser was heated to reflux overnight under a N2 purge. The mixture was then poured into water and extracted with 50mL dichloromethane (DCM). The combined organic layer was dried with anhydrous MgSO4 and evaporated to dryness. The crude product was purified by silica-gel column chromatography using hexane as eluent affording the title compound as a pale yellow solid (80% yield).
Reference： [1]Dyes and Pigments,2013,vol. 99,p. 105 - 115
  • 20
  • [ 177839-45-1 ]
  • [ 191162-39-7 ]
  • 2-(bromomethyl)-9,10-di (3-quinolinyl) anthracene [ No CAS ]
Reference： [1]Dyes and Pigments,2013,vol. 99,p. 105 - 115
  • 21
  • [ 130-15-4 ]
  • [ 177839-45-1 ]
Reference： [1]Dyes and Pigments,2013,vol. 99,p. 105 - 115
  • 22
  • [ 3319-24-2 ]
  • [ 177839-45-1 ]
Reference： [1]Dyes and Pigments,2013,vol. 99,p. 105 - 115
  • 23
  • [ 13922-41-3 ]
  • [ 177839-45-1 ]
  • [ 863497-34-1 ]
Reference： [1]Journal of Materials Chemistry C,2014,vol. 2,p. 8507 - 8514
  • 24
  • [ 177839-45-1 ]
  • 9,10-dibromo-2-(bromomethyl)anthracene [ No CAS ]
YieldReaction ConditionsOperation in experiment
90.5% With N-Bromosuccinimide; dibenzoyl peroxide; In tetrachloromethane; for 16.0h;Reflux; In a 100 mL one-necked round-bottomed flask, <strong>[177839-45-1]9,10-dibromo-2-methylanthracene</strong> (2.000 g, 5.7 mmol), NBS (1.100 g, 6.5 mmol), BPO (50 mg) were added in carbon tetrachloride (30 mL) and mixture was refluxed for 16 h. The solvent was removed in vacuum and recrystallize from tetrahydrofuran-ethonal to produce the product as a yellow solid (2,200 g, 90.5%).1H NMR (400 MHz, DMSO, δ): 8.57-8.59 (m, 4H), 7.63-7.67 (m, 3H), 4.78 (s, 2H).
Reference： [1]Tetrahedron Letters,2016,vol. 57,p. 1847 - 1851
  • 25
  • [ 177839-45-1 ]
  • diethyl ((9,10-dibromoanthracen-2-yl)methyl)phosphonate [ No CAS ]
Reference： [1]Tetrahedron Letters,2016,vol. 57,p. 1847 - 1851
  • 26
  • [ 177839-45-1 ]
  • (E)-4-(2-(9,10-dibromoanthracen-2-yl)vinyl)-N,N-diphenylaniline [ No CAS ]
Reference： [1]Tetrahedron Letters,2016,vol. 57,p. 1847 - 1851
  • 27
  • [ 177839-45-1 ]
  • (E)-4-(2-(9,10-di(naphthalen-2-yl)anthracen-2-yl)vinyl)-N,N-diphenylaniline [ No CAS ]
Reference： [1]Tetrahedron Letters,2016,vol. 57,p. 1847 - 1851
  • 28
  • [ 177839-45-1 ]
  • 9,10-dimethyl-2-anthracenecarboxaldehyde [ No CAS ]
Reference： [1]Tetrahedron Letters,2016,vol. 57,p. 1847 - 1851
  • 29
  • [ 177839-45-1 ]
  • N-phenyl-8-fluoro-1-naphthylamine [ No CAS ]
  • C47H32F2N2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% Three 500 ml bottle with magnetic stirrer, purged with argon were successively added sodium tert-butoxide 18.1g (0.188mol),<strong>[177839-45-1]9,10-dibromo-2-methylanthracene</strong> 27.5 g (purity 99%, 0.0785 mol) and xylene 100 ml.After argon substitution again, 1.6 ml of tri-tert-butylphosphine and 0.23 g of tris(diphenylbenzylacetone)dipalladium were successively added.After the addition was completed, the temperature was raised to 110 C by heating.A solution consisting of 48.1 g of N-phenyl-8-fluoro-1-naphthylamine (purity of 99%, 0.203 mol) and 100 ml of xylene was initially added dropwise, and the temperature was controlled at 110 to 120 C.The temperature was lowered to 50 C, hydrolyzed by adding 100 m of deionized water, stirred for 10 minutes, filtered, and the filter cake was boiled several times with DMF.36.3 g of a yellow product were obtained with a purity of 99% and a yield of 70%.
Reference： [1]Patent: CN108383735,2018,A .Location in patent: Paragraph 0074; 0075; 0077; 0080; 0081
  • 30
  • [ 575-24-6 ]
  • [ 177839-45-1 ]
  • C47H32F2N2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate; In 5,5-dimethyl-1,3-cyclohexadiene; at 110 - 120℃; 500 ml three-necked bottle with magnetic stirring, argon replacement followed by sodium tert-butoxide 18.1 g (0.188 mol),9,10-Dibromo-2-methylanthracene 27.5 g (purity 99%, 0.0785 mol) and xylene 100 ml. After argon substitution again, 1.6 ml of tri-tert-butylphosphine and 0.23 g of tris(diphenylbenzylacetone)dipalladium were successively added. After the addition,The temperature was raised to 110 C by heating. Start dropping at 48.1 g of N-(2-fluoro-phenyl)-1-naphthylamine (purity 99%, 0.203 mol)And a solution of 100 ml of xylene, temperature control 110-120 C. The temperature was lowered to 50 C, hydrolyzed by adding 100 m of deionized water, stirred for 10 minutes, filtered, and the filter cake was repeatedly boiled several times with DMF to obtain 39 g of a yellow product with a purity of 99%.The yield was 75%.
Reference： [1]Patent: CN108530306,2018,A .Location in patent: Paragraph 0074; 0075; 0077; 0080; 0081
  • 31
  • [ 177839-45-1 ]
  • N-phenyl-2-fluoro-1-naphthylamine [ No CAS ]
  • C47H32F2N2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate; In 5,5-dimethyl-1,3-cyclohexadiene; at 110 - 120℃;Inert atmosphere; 500 ml three-neck bottle with magnetic stirringAfter argon replacement, 18.1 g (0.188 mol) of sodium t-butoxide was sequentially added,27.5 g of 9,10-dibromo-2-methyl-anthracene (purity 99%, 0.0785mol) and xylene 100ml.After argon substitution again, 1.6 ml of tri-tert-butylphosphine and 0.23 g of tris(diphenylbenzylacetone)dipalladium were successively added.After the addition was completed, the temperature was raised to 110 C by heating.Start dropping at 48.1 g of N-phenyl-2-fluoro-1-naphthylamine (purity 99%, 0.203 mol)And a solution consisting of 100 ml of xylene,Temperature control 110-120 C.Cool down to 50 C, add 100m deionized water hydrolysis,Stir for 10 minutes, filter,The filter cake was boiled several times with DMF.36.3 g of a yellow product were obtained with a purity of 99% and a yield of 70%.
Reference： [1]Patent: CN108530305,2018,A .Location in patent: Paragraph 0073-0076; 0080; 0081
  • 32
  • [ 64959-31-5 ]
  • [ 177839-45-1 ]
  • C49H38N2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate; In 5,5-dimethyl-1,3-cyclohexadiene; at 50 - 120℃; 500 ml three-necked flask with magnetic stirring, followed by argon replacement with sodium tert-butoxide 18.1 g (0.188 mol), <strong>[177839-45-1]9,10-dibromo-2-methylanthracene</strong> 27.5 g (purity 99%, 0.0785 mol) and xylene 100ml.After argon substitution again, 1.6 ml of tri-tert-butylphosphine and 0.23 g of tris(diphenylbenzylacetone)dipalladium were successively added. After the addition was completed, the temperature was raised to 110 C by heating.Start to add dropwise to a solution consisting of 47.3 g of N-phenyl-2-methyl-1-naphthylamine (purity 99%, 0.203 mol) and 100 ml of xylene, temperature control110-120 C.The temperature was lowered to 50 C, hydrolyzed by adding 100 m of deionized water, stirred for 10 minutes, filtered, and the filter cake was boiled several times with DMF.37 g of a yellow product were obtained with a purity of 99% and a yield of 72%.
Reference： [1]Patent: CN108409584,2018,A .Location in patent: Paragraph 0075; 0078; 0081-0082
  • 33
  • [ 177839-45-1 ]
  • N-phenyl-8-methyl-1-naphthylamine [ No CAS ]
  • C49H38N2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate; In 5,5-dimethyl-1,3-cyclohexadiene; at 110 - 120℃;Inert atmosphere; 500 ml three-necked flask with magnetic stirring, followed by argon replacement with sodium tert-butoxide 18.1 g (0.188 mol), 9,10-dibromo-2-methylhydrazine 27.5 g (purity 99%, 0.0785 mol) and two Toluene 100ml. After argon replacement again, add sequentially1.6 ml of tri-tert-butylphosphine and 0.23 g of tris(diphenylbenzylacetone)dipalladium.After the addition was completed, the temperature was raised to 110 C by heating. Start dropping at 47.3gN-phenyl-8-methyl-1-naphthylamine (purity 99%, 0.203 mol) andA solution of 100 ml of xylene is temperature controlled at 110-120 C. Cool down to 50 C,Add 100m deionized water to hydrolyze, stir for 10 minutes, filter,The filter cake was boiled several times with DMF to give 36 g of a yellow product.The purity is 99% and the yield is 70%.
Reference： [1]Patent: CN108484417,2018,A .Location in patent: Paragraph 0081; 0082; 0084; 0087; 0088
  • 34
  • [ 634-41-3 ]
  • [ 177839-45-1 ]
  • C49H38N2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate; In 5,5-dimethyl-1,3-cyclohexadiene; toluene; at 110 - 120℃;Inert atmosphere; 500 ml three-necked flask with magnetic stirring, followed by argon replacement with sodium tert-butoxide 18.1 g (0.188 mol), <strong>[177839-45-1]9,10-dibromo-2-methylanthracene</strong> 27.5 g (purity 99%, 0.0785 mol) and two Toluene 100ml. After argon substitution again, 1.6 ml of tri-tert-butylphosphine and 0.23 g of tris(diphenylbenzylacetone)dipalladium were successively added. After the addition was completed, the temperature was raised to 110 C by heating. A solution of 47.3 g of N-(2-methyl-phenyl)-1-naphthylamine (purity of 99%, 0.203 mol) and 100 ml of xylene was started dropwise, and the temperature was controlled at 110 to 120 C. The mixture was cooled to 50 C, hydrolyzed by adding 100 m of deionized water, stirred for 10 minutes, filtered, and the filter cake was repeatedly boiled several times with DMF to obtain 40 g of a yellow product, purity 99%, yield 78%
Reference： [1]Patent: CN108658788,2018,A .Location in patent: Paragraph 0077; 0080; 0083; 0084
  • 35
  • [ 177839-45-1 ]
  • N-(2-fluorophenyl)-9-phenyl-9H-carbazol-3-amine [ No CAS ]
  • C63H42F2N4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate; In 5,5-dimethyl-1,3-cyclohexadiene; at 110 - 120℃;Inert atmosphere; 500 ml three-necked flask with magnetic stirring, followed by argon replacement followed by sodium tert-butoxide 18.1 g (0.188 mol),<strong>[177839-45-1]9,10-dibromo-2-methylanthracene</strong>27.5 g (purity 99%, 0.0785 mol) and xylene 100 ml.After argon substitution again, 1.6 ml of tri-tert-butylphosphine and 0.23 g of tris(dibenzylideneacetone)dipalladium were successively added.After the addition was completed, the temperature was raised to 110 C by heating.Starting to add dropwise to 71.58 g of N-(2-fluorophenyl)-9-diphenyl-9H-carbazol-3-amine(purity 99%, 0.203 mol)A solution consisting of 100 ml of xylene is temperature controlled at 110-120 C.The temperature was lowered to 50 C, hydrolyzed by adding 100 m of deionized water, stirred for 10 minutes, filtered, and the filter cake was boiled several times with DMF.50.47 g of a yellow product was obtained with a purity of 99% and a yield of 72%.
Reference： [1]Patent: CN109503460,2019,A .Location in patent: Paragraph 0065-0068; 0071-0073
  • 36
  • [ 177839-45-1 ]
  • C25H20N2 [ No CAS ]
  • C65H48N4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
79% With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate; In 5,5-dimethyl-1,3-cyclohexadiene; at 110 - 120℃;Inert atmosphere; 500 ml three-necked flask with magnetic stirring, followed by argon replacement with sodium tert-butoxide 18.1 g (0.188 mol), 9,2-Dibromo-2-methylindole 27.5 g (purity 99%, 0.0785 mol) and xylene 100 ml. After argon replacement again, add sequentially1.6 ml of tri-tert-butylphosphine and 0.23 g of tris(diphenylbenzylacetone)dipalladium. After the addition was completed, the temperature was raised to 110 C by heating. Start dropping atFrom 70.73 g of N-phenyl-9-tolyl-9H-indazole-3-amine (purity 99%, 0.203 mol) and 100 ml of xyleneSolution, temperature control 110-120 C. Cool down to 50 C, add 100m deionized water hydrolysis, stir for 10 minutes, filter, filter cake with DMFIt was boiled several times repeatedly to obtain 54.89 g of a yellow product, purity 99%, yield 79%.
Reference： [1]Patent: CN109608384,2019,A .Location in patent: Paragraph 0058; 0061; 0065; 0066; 0067
  • 37
  • [ 177839-45-1 ]
  • 8-fluoro-N,9-diphenyl-9H-carbazol-3-amine [ No CAS ]
  • C63H42F2N4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate; In 5,5-dimethyl-1,3-cyclohexadiene; toluene; at 100 - 110℃;Inert atmosphere; 500 ml three-neck bottle with magnetic stirring and after argon replacement, 18.1 g (0.188 mol) of sodium t-butoxide, 27.5 g of <strong>[177839-45-1]9,10-dibromo-2-methylanthracene</strong> (purity of 99%, 0.0785 mol) and 100 ml of xylene were sequentially added. After argon substitution again, 1.6 ml of tri-tert-butylphosphine and 0.23 g of tris(diphenylbenzylacetone)dipalladium were successively added. After the addition was completed, the temperature was raised to 110 C by heating. A solution consisting of 71.54 g of 8-fluoro-N,9-diphenyl-9H-carbazol-3-amine (purity: 99%, 0.203 mol) and 100 ml of toluene was added dropwise, and the temperature was controlled at 100 to 110 C. The temperature was lowered to 50 C, hydrolyzed by adding 100 m of deionized water, stirred for 10 minutes, filtered, and the filter cake was boiled several times with DMF to obtain 50.47 g of a yellow product, purity 99%, yield 72%.
Reference： [1]Patent: CN109503459,2019,A .Location in patent: Paragraph 0064; 0065; 0066; 0067; 0070; 0071; 0072
  • 38
  • [ 177839-45-1 ]
  • C25H20N2 [ No CAS ]
  • C65H48N4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate; In 5,5-dimethyl-1,3-cyclohexadiene; at 110 - 120℃;Inert atmosphere; 500 ml three-necked flask with magnetic stirring, followed by argon replacement followed by sodium tert-butoxide 18.1 g (0.188 mol),9,10-dibromo-2-methyl anthracene27.5 g (purity 99%, 0.0785 mol) and xylene 100 ml. After argon replacement again, add sequentially1.6 ml of tri-tert-butylphosphine and 0.23 g of tris(diphenylbenzylacetone)dipalladium. After the addition was completed, the temperature was raised to 110 C by heating. Start dropping atConsists of 70.73 g of 8-methyl-N,9-diphenyl-9H-indazole-3-amine (purity 99%, 0.203 mol) and 100 ml of xyleneThe solution is temperature controlled at 110-120 C. Cool down to 50 C, add 100m deionized water hydrolysis, stir for 10 minutes, filter, filter cakeThe DMF was repeatedly boiled several times to give 56.28 g of a yellow product with a purity of 99% and a yield of 81%.
Reference： [1]Patent: CN109608385,2019,A .Location in patent: Paragraph 0063; 0066; 00069; 0070; 0071
  • 39
  • [ 177839-45-1 ]
  • C25H20N2 [ No CAS ]
  • C65H48N4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate; In 5,5-dimethyl-1,3-cyclohexadiene; at 110℃;Inert atmosphere; 500 ml three-neck bottle with magnetic stirringAfter argon replacement, 18.1 g (0.188 mol) of sodium t-butoxide was sequentially added,9,10-Dibromo-2-methyl anthracene 27.5 g (purity 99%, 0.0785 mol) and xylene 100 ml.After argon substitution again, 1.6 ml of tri-tert-butylphosphine and 0.23 g of tris(diphenylbenzylacetone)dipalladium were successively added. After the addition was completed, the temperature was raised to 110 C by heating.Starting to add dropwise a solution consisting of 70.73 g of 4-methyl-N,9-diphenyl-9H-indazole-3-amine (purity 99%, 0.203 mol) and 100 ml of xylene.Temperature control 110-120 C. Cool down to 50 C,Add 100m deionized water to hydrolyze,Stir for 10 minutes, filter,The filter cake is boiled several times with DMF.Obtaining 52.11g of yellow product,99% purity,The yield was 75%.
Reference： [1]Patent: CN109608386,2019,A .Location in patent: Paragraph 0064; 0067; 0070; 0071
  • 40
  • [ 177839-45-1 ]
  • 3-bromo-4-fluoro-9-phenyl-9H-carbazole [ No CAS ]
  • C63H42F2N4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% With tri-tert-butyl phosphine; sodium ethanolate; bis(dibenzylideneacetone)-palladium(0); In 5,5-dimethyl-1,3-cyclohexadiene; at 110 - 120℃;Inert atmosphere; 500 ml three-necked flask with magnetic stirring, followed by argon replacement with sodium tert-butoxide 18.1 g (0.188 mol), 9,2-Dibromo-2-methylindole 27.5 g (purity 99%, 0.0785 mol) and xylene 100 ml. After argon replacement again, add sequentially1.6 ml of tri-tert-butylphosphine and 0.23 g of tris(diphenylbenzylacetone)dipalladium. After the addition was completed, the temperature was raised to 110 C by heating. Start dropping atFrom 71.54 g of 4-fluoro-N,9-diphenyl-9H-indazole-3-amine (purity 99%, 0.203 mol) and 100 ml of xyleneSolution, temperature control 110-120 C. Cool down to 50 C, add 100m deionized water hydrolysis, stir for 10 minutes, filter, filter cake with DMFIt was boiled several times repeatedly to obtain 50.47 g of a yellow product, purity 99%, yield 72%.
Reference： [1]Patent: CN109721526,2019,A .Location in patent: Paragraph 0065; 0068; 0071-0072
  • 41
  • [ 177839-45-1 ]
  • 9-(2-fluorophenyl)-N-phenyl-9H-carbazole-3-amine [ No CAS ]
  • C63H42F2N4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate; In 5,5-dimethyl-1,3-cyclohexadiene; at 110 - 120℃;Inert atmosphere; 500 ml three-neck bottle with magnetic stirringAfter argon replacement, 18.1 g (0.188 mol) of sodium t-butoxide was sequentially added,9,10-dibromo-2-methylindole27.48 g (purity 99%, 0.0785 mol) and xylene 100 ml.After argon substitution again, 1.6 ml of tri-tert-butylphosphine and 0.23 g of tris(diphenylbenzylacetone)dipalladium were successively added. After the addition was completed, the temperature was raised to 110 C by heating.Starting to add dropwise to 71.54g of 9-(2-fluorophenyl)-N-phenyl-9H-indazole-3-amine (purity 99%, 0.203 mol) and 100 ml of xyleneThe composition of the solution, temperature control 110-120 C. Cool down to 50 C,Add 100m deionized water to hydrolyze, stir for 10 minutes, filter,The filter cake was boiled several times with DMF to give 50.47 g of a yellow product.The purity was 99% and the yield was 72%.
Reference： [1]Patent: CN109574911,2019,A .Location in patent: Paragraph 0066; 0072-0073
  • 42
  • [ 177839-45-1 ]
  • C25H20N2 [ No CAS ]
  • C65H48N4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate; In 5,5-dimethyl-1,3-cyclohexadiene; at 110 - 120℃;Inert atmosphere; A 500 ml three-neck bottle with magnetic stirringAfter argon replacement, 18.1 g (0.188 mol) of sodium tert-butoxide was added in sequence.9,10-Dibromo-2-methylindole 27.5 g (purity 99%, 0.0785 mol) and xylene 100 ml. After argon substitution again, 1.6 ml of tri-tert-butylphosphine and 0.23 g of tris(diphenylbenzylacetone)dipalladium were successively added. After the addition was completed, the temperature was raised to 110 C by heating. Starting to add dropwise to 70.73 g of 9-phenyl-N-tolyl-9H-indazole-3-amine (purity 99%, 0.203 mol) and 100 ml of xyleneThe composition of the solution, temperature control 110-120 C. The mixture was cooled to 50 C, hydrolyzed by adding 100 m of deionized water, stirred for 10 minutes, filtered, and the filter cake was boiled several times with DMF to obtain 59.06 g of a yellow product, purity 99%, yield 85%
Reference： [1]Patent: CN109608383,2019,A .Location in patent: Paragraph 0066; 0067; 0068; 0069; 0070; 0073; 0074

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