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Chemical Structure| 1357634-60-6
Chemical Structure| 1357634-60-6
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Product Details of [ 1357634-60-6 ]

CAS No. :1357634-60-6 MDL No. :MFCD30737495
Formula : C24H24BNO2 Boiling Point : -
Linear Structure Formula :- InChI Key :KQQUPCGBWUTWMK-UHFFFAOYSA-N
M.W : 369.26 Pubchem ID :129319311
Synonyms :

Safety of [ 1357634-60-6 ]

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 [ 1357634-60-6 ]

* 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 [ 1357634-60-6 ]

[ 1357634-60-6 ] Synthesis Path-Downstream   1~33

  • 1
  • [ 902518-11-0 ]
  • [ 1357634-60-6 ]
  • 9,9'-biphenyl-2,2'-diylbis-9H-carbazole [ No CAS ]
  • 2
  • [ 3842-55-5 ]
  • [ 1357634-60-6 ]
  • 9-(2-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-9H-carbazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water at 80℃; for 24h; Preparation of 9-(2-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-9H-carbazole (CzTrz) 9-(2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-9Hcarbazole(3 g, 8.12 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine(2.61 g, 9.75 mmol), and tetrakis(triphenylphosphine)palladium(0) (0.28 g, 0.24 mmol) were dissolved in 2 M potassiumcarbonate solution (40 mL) and tetrahydrofuran (100 mL). The reactionmixture was stirred for 24 h at 80 C. The mixture wasdiluted with dichloromethane and washed thrice with distilledwater (100 mL). The organic layer was dried over anhydrous MgSO4and evaporated in vacuo to yield the crude product, which waspurified through column chromatography using dichloromethane/n-hexane to yield a pale yellow powder. The other dopants, mCzTrzand tCzTrz, were prepared through procedures similar to thosedescribed above.CzTrz Yield 86%. Tg: 124.6 C, Tm: 211.9 C, Td: 365.9 C (5%weight loss). 1H NMR (500 MHz, CDCl3): d 7.02e7.24 (m, 4H), 7.33 (t,6H, J 16 Hz), 7.48 (t, 2H, J 14.4 Hz), 7.73 (d, 1H, J 8.8 Hz), 7.78 (t,1H, J 15.2 Hz), 7.84 (t, 1H, J 15.2 Hz), 8.03 (t, 6H, J 17.6 Hz), 8.57(d, 1H, J 7.6 Hz). 13C NMR (CDCl3): d 109.5, 119.5, 120.2, 123.4,125.9, 128.3, 128.7, 128.8, 130.6, 132.3, 132.5, 132.7, 135.4, 136.1,141.7, 171.2, 172.1. MS (EI) m/z 474 [(MH)]. Anal Calcd forC33H22N4: C, 83.52%; H, 4.67%; N,11.81%. Found: C, 83.52%; H, 4.74%;N, 11.69%.
  • 3
  • [ 86-74-8 ]
  • [ 1357634-60-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: copper (I) iodide; potassium carbonate / N,N-dimethyl acetamide / 24 h / Inert atmosphere; Reflux 2: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II) dichloromethane adduct; anhydrous potassium acetate / 1,4-dioxane / 24 h / 80 °C / Inert atmosphere
Multi-step reaction with 2 steps 1: copper (I) iodide; potassium carbonate / N,N-dimethyl acetamide / 24 h / Inert atmosphere; Reflux 2: palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; anhydrous potassium acetate / 1,4-dioxane / 24 h / 80 °C / Inert atmosphere
Multi-step reaction with 2 steps 1: copper (I) iodide; tripotassium phosphate tribasic; (±)-trans-1,2-diaminocyclohexane / toluene / 4 h 2: palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; anhydrous potassium acetate / 1,4-dioxane / 6 h
  • 4
  • [ 583-53-9 ]
  • [ 1357634-60-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: copper(l) iodide; potassium carbonate / N,N-dimethyl acetamide / 24 h / Inert atmosphere; Reflux 2: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate / 1,4-dioxane / 24 h / 80 °C / Inert atmosphere
Multi-step reaction with 2 steps 1: copper(l) iodide; potassium carbonate / N,N-dimethyl acetamide / 24 h / Inert atmosphere; Reflux 2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,4-dioxane / 24 h / 80 °C / Inert atmosphere
  • 5
  • [ 902518-11-0 ]
  • [ 73183-34-3 ]
  • [ 1357634-60-6 ]
YieldReaction ConditionsOperation in experiment
80% Under the protection of nitrogen atmosphere,2-bromobenzoxazole10mmol and bis(pinacol) diboron 10mmol were added to the three-necked bottle.Add 50 mL of dioxane to stir to dissolve, and pass nitrogen for 30 min. Add potassium acetate 10mmol,The temperature was raised to 100 ° C and the reaction was stirred for 12 h.The crude product was purified by silica gel column chromatography.The eluent is a 2:1 dichloromethane-n-hexane mixed solvent. A white crystalline product was obtained in a yield of 80percent.
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate; In 1,4-dioxane; at 80℃; for 24h;Inert atmosphere; A mixture of <strong>[902518-11-0]9-(2-bromophenyl)-9H-carbazole</strong> (10 g,31.04 mmol), 4,4,40,40,5,5,50,50-octamethyl-2,20-bi(1,3,2-dioxaborolane) (10.25 g, 40.35 mmol), 1,10-bis(diphenylphosphino)ferrocene-palladium(II) dichloride dichloromethanecomplex (0.76 g, 0.93 mmol), potassium acetate (9.14 g,93.11 mmol), and anhydrous 1,4-dioxane (180 mL) was degassedwith nitrogen for 1 h while stirring. The reaction mixture was thenmaintained under a nitrogen atmosphere at 80 C for 24 h. Themixture was diluted with dichloromethane and washed thrice withdistilled water (100 mL). The organic layer was dried over anhydrousMgSO4 and evaporated in vacuo to yield the crude product,which was purified through column chromatography usingdichloromethane/n-hexane to obtain a white powder. Other intermediatecompounds, 3,6-dimethyl-9-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-9H-carbazole and 3,6-di-tert-butyl-9-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-9Hcarbazolewere prepared by similar procedures described above.1H NMR (500 MHz, CDCl3): d 0.79 (s, 12H), 7.18 (d, 2H, J 12 Hz),7.25 (t, 2H, J 18 Hz), 7.37 (t, 2H, J 18 Hz), 7.53 (t, 2H, J 18 Hz),7.69 (t, 1H, J 16 Hz), 7.96 (d, 1H, J 12 Hz), 8.14 (d, 2H, J 12 Hz).
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 80℃; for 24h;Inert atmosphere; A mixture of <strong>[902518-11-0]9-(2-bromophenyl)-9H-carbazole</strong> (10 g,31.04 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (10.25 g, 40.35 mmol), 1,1'-bis(diphenylphosphino)ferrocene-palladium(II) dichloride dichloromethane complex(0.76 g, 0.93 mmol), potassium acetate (9.14 g, 93.11 mmol),and anhydrous 1,4-dioxane (180 ml) was degassed with nitrogenfor 1 h while stirring. The reaction mixture was then maintained innitrogen at 80 °C for 24 h. The mixture was diluted withdichloromethane and washed with distilled water (100 mL) threetimes. The organic layer was dried over anhydrous MgSO4 andevaporated in vacuo to give the crude product, which was purifiedby column chromatography using dichloromethane/n-hexane andgave a white powder.1H NMR (500 MHz, CDCl3): delta 0.79 (s, 12H), 7.18 (d, 2H, J = 12 Hz),7.25 (t, 2H, J = 18 Hz), 7.37 (t, 2H, J = 18 Hz), 7.53 (t, 2H, J = 18 Hz),7.69 (t, 1H, J = 16 Hz), 7.96 (d, 1H, J = 12 Hz), 8.14 (d, 2H, J = 12 Hz).13C NMR (CDCl3): delta 24.4, 83.4, 109.7, 119.1, 119.9, 123.1, 125.5, 127.6,128.6, 132.1, 136.3, 142.1, 142.4.
  • 6
  • [ 1700-02-3 ]
  • [ 1357634-60-6 ]
  • 9,9'-((6-phenyl-1,3,5-triazine-2,4-diyl)bis(2,1-phenylene))bis(9H-carbazole) [ No CAS ]
YieldReaction ConditionsOperation in experiment
71% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran at 80℃; for 24h; 2.4. Preparation of 9,9'-((6-phenyl-1,3,5-triazine-2,4-diyl)bis(2,1-phenylene))bis(9H-carbazole) (BisCz-Trz) 9-(2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-9Hcarbazole(11.04 g, 27.87 mmol), 2,4-dichloro-6-phenyl-1,3,5-triazine (3 g, 13.27 mmol), and tetrakis(triphenylphosphine)palladium(0) (1.53 g, 1.33 mmol) were dissolved in a 2 M potassiumcarbonate solution (40 mL) and tetrahydrofuran (100 mL). The reactionmixture was stirred for 24 h at 80 °C. The mixture wasdiluted with dichloromethane and washed with distilled water(100 mL) three times. The organic layer was dried over anhydrousMgSO4 and evaporated in vacuo to give the crude product, whichwas purified by column chromatography using dichloromethane/nhexaneand gave a pale yellow powder.BisCz-Trz: Yield 71%. Tg: 100 °C, Tm: 263 °C, Td: 374 °C (5%weight loss). 1H NMR (500 MHz, CDCl3): δ 6.79 (d, 2H, J = 8 Hz),6.895 (t, 2H, J = 15 Hz), 6.965 (d, 4H, J = 8 Hz), 7.163-7.217 (m, 5H),7.263 (t, 4H, J = 15 Hz), 7.478 (t, 2H, J = 15 Hz), 7.563 (d, 2H,J = 8 Hz), 7.659-7.708 (m, 4H), 7.986 (d, 4H, J = 8 Hz). 13C NMR(CDCl3): δ 109.4, 119.4, 120.1, 123.3, 125.9, 127.8, 128.4, 128.6, 130.4,131.9, 132.4, 132.6, 135.3, 136.4, 141.5. Mass (EI) m/z 639 [(M+H)+].Anal Calcd for C45H29N5: C, 84.48%; H, 4.57%; N, 10.95%. Found: C,84.48%; H, 4.57%; N, 10.86%. UV-vis: λmax 339 (THF) nm. Fluorescence: λmax (emission) 457 (solid state) nm. Φfl 0.756.
  • 7
  • [ 108-77-0 ]
  • [ 1357634-60-6 ]
  • 2,4,6-tris(2-(9H-carbazol-9-yl)phenyl)-1,3,5-triazine [ No CAS ]
YieldReaction ConditionsOperation in experiment
37% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran at 80℃; for 24h; 2.5. Preparation of 2,4,6-tris(2-(9H-carbazol-9-yl)phenyl)-1,3,5-triazine (TrisCz-Trz) 9-(2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-9Hcarbazole(15.36 g, 53.68 mmol), 2,4,6-trichloro-6-1,3,5-triazine(3 g, 16.27 mmol), and tetrakis(triphenylphosphine)palladium(0)(2.82 g, 2.44 mmol) were dissolved in a 2 M potassium carbonatesolution (40 mL) and tetrahydrofuran (100 mL). The reactionmixture was stirred for 24 h at 80 °C. The mixture was diluted withdichloromethane and washed with distilled water (100 mL) three times. The organic layer was dried over anhydrous MgSO4 andevaporated in vacuo to give the crude product, which was purifiedby column chromatography using dichloromethane/n-hexane andgave a pale yellow powder.TrisCz-Trz: Yield 37%. Tg: 126 °C, Tm: 323 °C, Td: 395 °C (5%weight loss). 1H NMR (500 MHz, CDCl3): δ 6.238 (d, 3H, J = 8 Hz),6.558 (d, 6H, J = 8 Hz), 6.968 (t, 3H, J = 15 Hz), 7.216-7.261 (m,12H),7.341 (d, 3H, J = 8 Hz), 7.485 (t, 3H, J = 15 Hz), 8.100 (d, 6H, J = 7 Hz).13C NMR (CDCl3): δ 109.4, 119.2, 123.2, 125.9, 128.2, 130.0, 132.2,133.6, 136.0, 141.3, 170.2. Mass (EI) m/z 803 [(M+H)+]. Anal Calcdfor C57H36N6 C, 85.05%; H, 4.51%; N, 10.44%. Found: C, 85.07%; H,4.49%; N, 10.45%. UV-vis: λmax 339 (THF) nm. Fluorescence: λmax(emission) 457 (solid state) nm. Φfl 0.708.
  • 8
  • [ 566939-58-0 ]
  • [ 1357634-60-6 ]
  • 1,3-bis[2-(9H-carbazol-9-yl)phenyl]-5-octyl-4H-thieno[3,4-c]pyrrole-4,6(5H)-dione [ No CAS ]
  • 9
  • [ 1357634-60-6 ]
  • 4'-(5-bromo-3-ethyl-2-(pyridin-4-yl)-3H-benzo[e]indol-1-yl)-4-(9H-carbazol-9-yl)-[1,1'-biphenyl]-3-carbonitrile [ No CAS ]
  • 4'-(5-(2-(9H-carbazol-9-yl)phenyl)-3-ethyl-2-(pyridin-4-yl)-2,3-dihydro-1H-benzo[e]indol-1-yl)-4-(9H-carbazol-9-yl)-[1,1'-biphenyl]-3-carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
24.1% With tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamide at 95℃; for 12h; Inert atmosphere; 1.6 Step 6 Add compound e to the reaction flask4'-(5-bromo-2-(pyridin-4-yl)-3H-benzo[e]indol-1-yl)-4-(9H-carbazol-9-yl)-[1,1 '-biphenyl]-3-carbonitrile (0.08069 g, 0.1163 mmol), 9-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane- 2-yl)phenyl)-9H-carbazole (0.04296 g, 0.1170 mmol) and tetrachlorotriphenylphosphine palladium (0) (0.0010 g, 0.007 mmol) was added under nitrogen atmosphere to remove nitrogen three times. A 3:1 volume ratio of DMF and (2M) K2CO3 solution was added to the reaction flask for reaction.The reaction temperature is 95° C., and the reaction is stopped after 12 h, and extracted with ethyl acetate and deionized water for 2-3 times.The upper organic phase was dried over anhydrous magnesium sulfate and evaporated to dryness. Column chromatography (eluent is ethyl acetate:Petroleum ether = 1:2) gave 0.024 g (yield 24.1%) of a yellow powder of CzCNPyCa-1.
  • 10
  • [ 90-90-4 ]
  • [ 1357634-60-6 ]
  • C31H21NO [ No CAS ]
YieldReaction ConditionsOperation in experiment
66% Stage #1: (4-bromophenyl)(phenyl)methanone; 9-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane- 2-yl)phenyl)-9H-carbazole With potassium carbonate In water; toluene for 0.0833333h; Inert atmosphere; Stage #2: With tetrakis(triphenylphosphine) palladium(0) In water; toluene for 36h; Reflux; 3.2 (2) Synthesis of the final product [4-(2-benzoxazole) benzophenone] 4-bromobenzophenone 10mmol under nitrogen atmosphere protectionAnd 12mmol of 2-carbazole phenylborate was added to the three-necked bottle.Add 50 mL of toluene and stir to dissolve.Adding potassium carbonate aqueous solution 14mmol / 2ml H2O and 0.5ml phase transfer agent,After stirring for 5 minutes,0.05 g of tetrakistriphenylphosphine palladium was added as a catalyst.After stirring at reflux for 36 h, the reaction solution was cooled and suction filtered.The filtrate was evaporated to dryness using a rotary evaporator.Purification by silica gel column chromatography,The eluent was a mixed solution of dichloromethane and n-hexane in a volume ratio of 2:1.The white crystalline product was obtained in a yield of 66%.
  • 11
  • [ 1357634-60-6 ]
  • C37H45ClFN3 [ No CAS ]
  • C55H57FN4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tris-(dibenzylideneacetone)dipalladium(0); potassium acetate; XPhos In 1,4-dioxane; water; toluene at 100℃;
  • 12
  • [ 1353056-40-2 ]
  • [ 1357634-60-6 ]
  • C41H25Br2N3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; potassium carbonate; tri tert-butylphosphoniumtetrafluoroborate In water; toluene at 20℃; Inert atmosphere; Under nitrogen protection, weigh compounds S22 (2.5 mmol), S23 (5.5 mmol),[Pd2 (dba) 3] · CHCl3 (0.12mmol) and HP (tBu) 3 · BF4 (0.24mmol),Add to a 250 mL two-necked flask. Inject 80mL of toluene into the two-necked flask (pass N2 for 15min to remove oxygen in advance),Then, 5.8 mL of a 1M K2CO3 aqueous solution (N2 was removed in advance for 15 minutes to remove oxygen) was added dropwise, and the mixture was stirred at room temperature overnight.After the reaction was completed, 25 mL of deionized water was added, and a few drops of 2M HCl were added dropwise.Extract with dichloromethane, collect the organic phase, and dry over anhydrous Na2SO4.The dried solution was filtered, and the solvent was removed on a rotary evaporator to obtain a crude product.The crude product was purified by a silica gel column, and finally purified to obtain solid S24 (1.9 mmol, 76%).
  • 13
  • [ 1357634-60-6 ]
  • C4Br2I2S [ No CAS ]
  • C40H24Br2N2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
68% With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; potassium carbonate; tri tert-butylphosphoniumtetrafluoroborate In water; toluene at 20℃; Inert atmosphere; 1 Example 1; Synthesis of compound P1 Under nitrogen protection, weigh compounds S1 (2.2 mmol), S2 (4.8 mmol),[Pd2 (dba) 3] · CHCl3 (0.10 mmol) and HP (t-Bu) 3 · BF4 (0.20 mmol),Add to a 250 mL two-necked flask.Inject 70mL of toluene into the two-necked flask (pass N2 in advance for 15min to remove oxygen),Then, 5 mL of a 1M K2CO3 aqueous solution was added dropwise (except for N215min in advance to remove oxygen), and stirred at room temperature overnight.After the reaction, 20 mL of deionized water was added, and a few drops of 2M HCl were added dropwise.Extract with dichloromethane, collect the organic phase, and dry over anhydrous Na2SO4.The dried solution was filtered, and the solvent was removed on a rotary evaporator to obtain a crude product.The crude product was purified by a silica gel column, and finally purified to obtain solid S20 (1.5 mmol, 68%).
  • 14
  • [ 1357634-60-6 ]
  • C20H10BrN3 [ No CAS ]
  • C38H22N4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
13 g With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water 1 Synthesis of Compound EH1 16 g (43 mmol, 1 eq) of Intermediate EH1(1), 31.7 g (86 mmol, 2 eq) of Compound I-3, 23.8 g (172 mmol, 4 eq) of potassium carbonate (K2CO3), and 2.3 g (2 mmol, 0.05 eq) of Pd(PPh3)4 were added to a mixed solution of 110 ml of tetrahydrofuran (THF) and 85 ml of water, and the resulting mixed solution was stirred at a temperature of 85° C. overnight (by using a pressure reactor). The mixed solution thus obtained was cooled to room temperature, and the reaction mixture was extracted with ethyl acetate. The resulting organic layer was dried by using MgSO4, filtered, and concentrated in vacuo to remove the solvent. A resulting product obtained therefrom was separated and purified by silica gel column chromatography, thereby obtaining 13 g of Compound EH1 (purity of 99.95% by LC-MS). LC-Mass Cal.: 534.18 g/mol, Measured.: M+1=535.18 g/mol
  • 15
  • [ 1357634-60-6 ]
  • C21H9BrN4 [ No CAS ]
  • C39H21N5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
13 g With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water 2 Synthesis of Compound EH2 16 g (40 mmol, 1 eq) of Intermediate EH2(1), 22.2 g (60 mmol, 1.5 eq) of Compound I-3, 16.8 g (120 mmol, 3 eq) of potassium carbonate (K2CO3), and 2.2 g (2 mmol, 0.05 eq) of Pd(PPh3)4 were added to a mixed solution of 300 ml of tetrahydrofuran (THF) and 75 ml of water, and the resulting mixed solution was stirred at a temperature of 85° C. overnight (by using a pressure reactor). The mixed solution thus obtained was cooled to room temperature, and the reaction mixture was extracted with ethyl acetate. The resulting organic layer was dried by using MgSO4, filtered, and concentrated in vacuo to remove the solvent. A resulting product obtained therefrom was separated and purified by silica gel column chromatography, thereby obtaining 13 g (purity of 99.90% by LC-MS) of Compound EH2.LC-Mass Cal.: 559.18 g/mol, Measured.: M+1=560.18 g/mol
  • 16
  • [ 1357634-60-6 ]
  • [ 55758-02-6 ]
  • C24H15N3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
32% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; for 18h;Reflux; General procedure: 5.00 grams (g) (13.5 millimoles, mmol) of 9-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-9H-carbazole, 2.73 g (14.9 mmol) of 6-bromopicolinonitrile, 0.782 g (0.680 mmol) of tetrakistriphenylphosphine palladium (0) (Pd(PPh3)4, and 4.68 g (33.9 mmol) of potassium carbonate were added to a mixture including 30 mL of THF and 15 mL of water, and the resulting mixture was stirred under reflux for 18 hours. After completion of the reaction, the reaction mixture was cooled to room temperature and the aqueous layer was removed therefrom through extraction. The organic layer was filtered under reduced pressure through a silica gel, and the filtrate was concentrated under reduced pressure. The product was filtered to obtain Compound 1 (3.37 g, the yield of 72%) by silica gel column chromatography. LC-Mass (calculated: 345.13 g/mol, found: M+1=346 g/mol)
  • 17
  • [ 1357634-60-6 ]
  • C24H12Br3N9 [ No CAS ]
  • C78H48N12 [ No CAS ]
YieldReaction ConditionsOperation in experiment
45% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; toluene at 80℃; for 24h; Inert atmosphere; 1 Synthesis of compound 1-1: Compound TTT-Br (200mg, 0.3mmol),2-(9-carbazolyl) phenylboronic acid pinacol ester (665 mg, 1.8 mmol),Tetrakis(triphenyl)palladium (51 mg, 0.045 mmol),potassium carbonate (2mol/L, 5mL) and10mL: 30mL mixed solution of ethanol and toluene was added to a 100mL single-neck bottle,The mixture was heated to reflux at 80°C for 24h under nitrogen protection.After the reaction was completed, it was cooled to room temperature, the toluene was removed by rotary evaporation under reduced pressure, and the reaction solution was extracted with dichloromethane (4×30 mL).The collected organic layers were washed with water (50 mL),Drying and distillation under reduced pressure to remove the solvent,The residue was separated by column chromatography with dichloromethane as the eluent to obtain 155 mg of white solid with a yield of 45%.
  • 18
  • [ 583-55-1 ]
  • [ 1357634-60-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: copper (I) iodide; tripotassium phosphate tribasic; (±)-trans-1,2-diaminocyclohexane / toluene / 4 h 2: palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; anhydrous potassium acetate / 1,4-dioxane / 6 h
  • 19
  • [ 1357634-60-6 ]
  • C54H38N2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: tetrakis-(triphenylphosphine)-palladium; potassium carbonate / toluene; ethanol; lithium hydroxide monohydrate / 4 h 2: palladium diacetate; sodium tertiary butoxide; tri-tert-butyl phosphine / toluene / 1.5 h
  • 20
  • [ 1357634-60-6 ]
  • [ 105946-82-5 ]
  • C30H20BrN [ No CAS ]
YieldReaction ConditionsOperation in experiment
54% With tetrakis-(triphenylphosphine)-palladium; potassium carbonate In ethanol; lithium hydroxide monohydrate; toluene for 4h; A1-1 Synthesis of Intermediate A(1)-P1 P2 (60 g, 1 eq.), 4-bromo-4′-iodo-1,1′-biphenyl (63 g, 1.3 eq.), Pd(PPh3)4 (7.8 g, 0.05 eq.), K2CO3 (28 g, 1.5 eq.), toluene (600 ml), ethanol (100 ml) and H2O (100 ml) were introduced to a 1-neck-round bottom flask (1-neck-r.b.f), and stirred for 4 hours. (0143) The reaction solution completed with the stirring was hot filtered twice only with methylene chloride (MC) to obtain P1 (33 g). (0144) Step yield=54%
  • 21
  • [ 591-18-4 ]
  • [ 1357634-60-6 ]
  • [ 2417210-67-2 ]
YieldReaction ConditionsOperation in experiment
66% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene at 80℃; Inert atmosphere; 8 Synthesis of Intermediate IM-15 In an Ar atmosphere, in a 1000 mL three-neck flask, 9-[2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-9H-carbazole (25.00 g, 67.7 mmol), 1-bromo-3-iodobenzene (19.15 g, 1.1 equiv, 67.7 mmol), K2CO3(28.07 g, 3.0 equiv, 203.1 mmol), Pd(PPh3)4(3.91 g, 0.05 equiv, 3.4 mmol), and a mixed solution of toluene/EtOH/H2O (4/2/1) (473 mL) were sequentially added and heated and stirred at about 80° C. After air-cooled to room temperature, the reaction solution was extracted with toluene. A water layer was removed, and the organic layers were washed with saturated saline and then dried over MgSO4. The compound MgSO4was filtered off and the organic layers were concentrated, and then the resulting crude product was purified by silica gel column chromatography (using a mixed solvent of hexane and toluene as an eluent) to obtain Intermediate IM-15 (17.80 g, yield 66%).By measuring FAB-MS, a mass number of m/z=398 was observed by molecular ion peak, thereby identifying Intermediate IM-15.
66 % With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene at 80℃; Inert atmosphere; 8 Synthesis of Intermediate IM-15 In an Ar atmosphere, in a 1000 mL three-neck flask, 9-[2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-9H-carbazole (25.00 g, 67.7 mmol), 1-bromo-3-iodobenzene (19.15 g, 1.1 equiv, 67.7 mmol), K2CO3(28.07 g, 3.0 equiv, 203.1 mmol), Pd(PPh3)4(3.91 g, 0.05 equiv, 3.4 mmol), and a mixed solution of toluene/EtOH/H2O (4/2/1) (473 mL) were sequentially added and heated and stirred at about 80° C. After air-cooled to room temperature, the reaction solution was extracted with toluene. A water layer was removed, and the organic layers were washed with saturated saline and then dried over MgSO4. The compound MgSO4was filtered off and the organic layers were concentrated, and then the resulting crude product was purified by silica gel column chromatography (using a mixed solvent of hexane and toluene as an eluent) to obtain Intermediate IM-15 (17.80 g, yield 66%).By measuring FAB-MS, a mass number of m/z=398 was observed by molecular ion peak, thereby identifying Intermediate IM-15.
66 % With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene at 80℃; Inert atmosphere; 8 Synthesis of Intermediate IM-15 In an Ar atmosphere, in a 1000 mL three-neck flask, 9-[2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-9H-carbazole (25.00 g, 67.7 mmol), 1-bromo-3-iodobenzene (19.15 g, 1.1 equiv, 67.7 mmol), K2CO3(28.07 g, 3.0 equiv, 203.1 mmol), Pd(PPh3)4(3.91 g, 0.05 equiv, 3.4 mmol), and a mixed solution of toluene/EtOH/H2O (4/2/1) (473 mL) were sequentially added and heated and stirred at about 80° C. After air-cooled to room temperature, the reaction solution was extracted with toluene. A water layer was removed, and the organic layers were washed with saturated saline and then dried over MgSO4. The compound MgSO4was filtered off and the organic layers were concentrated, and then the resulting crude product was purified by silica gel column chromatography (using a mixed solvent of hexane and toluene as an eluent) to obtain Intermediate IM-15 (17.80 g, yield 66%).By measuring FAB-MS, a mass number of m/z=398 was observed by molecular ion peak, thereby identifying Intermediate IM-15.
  • 22
  • [ 1357634-60-6 ]
  • [ 2417210-68-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / toluene; ethanol; water / 80 °C / Inert atmosphere 2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / N,N-dimethyl-formamide / Inert atmosphere; Reflux
  • 23
  • [ 1357634-60-6 ]
  • [ 2839715-21-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / toluene; ethanol; water / 80 °C / Inert atmosphere 2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / N,N-dimethyl-formamide / Inert atmosphere; Reflux 3: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / toluene; ethanol; water / 80 °C / Inert atmosphere
  • 24
  • [ 1357634-60-6 ]
  • [ 2248674-24-8 ]
  • [ 2641838-84-6 ]
YieldReaction ConditionsOperation in experiment
With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate Inert atmosphere; Heating;
  • 25
  • [ 1357634-60-6 ]
  • [ 2922950-90-9 ]
  • [ 2922947-10-0 ]
YieldReaction ConditionsOperation in experiment
68 % With bis(tri-t-butylphosphine)palladium(0); potassium carbonate In tetrahydrofuran; water Reflux; 45 Synthesis Example 45 im-3-13 (15 g, 24.3 mmol) and im-a-5 (9.4 g, 25.5 mmol) were added to 300 ml of THF and stirred and refluxed. Thereafter, potassium carbonate (10.1g, 72.9mmol) was dissolved in 100 ml of water, and after stirring sufficiently, bis(tri-tert-butylphosphine)palladium(0) (0.1g, 0.2mmol) was added. After reacting for 5 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 13.6 g of Compound 45. (yield 68%)
  • 26
  • [ 1357634-60-6 ]
  • [ 2922950-49-8 ]
  • [ 2922950-43-2 ]
YieldReaction ConditionsOperation in experiment
64 % With bis(tri-t-butylphosphine)palladium(0); potassium carbonate In tetrahydrofuran; water Reflux; 5 Synthesis Example 5 Im-1-3 (15 g, 30.9 mmol) and im-a-5 (12 g, 32.5 mmol) were added to 300 ml of THF and stirred and refluxed. Thereafter, potassium carbonate (12.8g, 92.8mmol) was dissolved in 100 ml of water, and after stirring sufficiently, bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.3mmol) was added. After reacting for 5 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 13.7 g of Compound 5. (Yield 64%)
  • 27
  • [ 1357634-60-6 ]
  • [ 2922951-02-6 ]
  • [ 2922946-98-1 ]
YieldReaction ConditionsOperation in experiment
65 % With bis(tri-t-butylphosphine)palladium(0); potassium carbonate In tetrahydrofuran; water Reflux; 57 Synthesis Example 57 im-4-7 (15 g, 24.3 mmol) and im-a-5 (9.4 g, 25.5 mmol) were added to 300 ml of THF and stirred and refluxed. Thereafter, potassium carbonate (10.1g, 72.9mmol) was dissolved in 100 ml of water, and after stirring sufficiently, bis(tri-tert-butylphosphine)palladium(0) (0.1g, 0.2mmol) was added. After reacting for 4 hours, the mixture was cooled to room temperature, and the organic layer and the water layer were separated and the organic layer was distilled. 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 13 g of compound 57. (yield 65%)
  • 28
  • [ 1357634-60-6 ]
  • [ 2922951-13-9 ]
  • [ 2922949-66-2 ]
YieldReaction ConditionsOperation in experiment
66 % With bis(tri-t-butylphosphine)palladium(0); potassium carbonate In tetrahydrofuran; water Reflux; 72 Synthesis Example 72 Im-5-8 (15 g, 28.6 mmol) and im-a-5 (11.1 g, 30 mmol) were added to 300 ml of THF and stirred and refluxed. Thereafter, potassium carbonate (11.8g, 85.7mmol) was dissolved in 100 ml of water, and after stirring sufficiently, bis(tri-tert-butylphosphine)palladium(0) (0.1g, 0.3mmol) was added. After reacting for 2 hours, it was cooled to room temperature, and the organic layer and the water layer were separated, and the organic layer was distilled. 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 13.8 g of Compound 72. (yield 66%)
  • 29
  • [ 1357634-60-6 ]
  • [ 2922951-14-0 ]
  • [ 2922947-14-4 ]
YieldReaction ConditionsOperation in experiment
64 % With bis(tri-t-butylphosphine)palladium(0); potassium carbonate In tetrahydrofuran; water Reflux; 73 Synthesis Example 73 Im-5-9 (15 g, 24.3 mmol) and im-a-5 (9.4 g, 25.5 mmol) were added to 300 ml of THF and stirred and refluxed. Thereafter, potassium carbonate (10.1g, 72.9mmol) was dissolved in 100 ml of water, and after stirring sufficiently, bis(tri-tert-butylphosphine)palladium(0) (0.1g, 0.2mmol) was added. After reacting for 4 hours, the mixture was cooled to room temperature, and the organic layer and the water layer were separated and the organic layer was distilled. 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 12.8 g of Compound 73. (yield 64%)
  • 30
  • [ 1357634-60-6 ]
  • [ 2922951-25-3 ]
  • [ 2922950-11-4 ]
YieldReaction ConditionsOperation in experiment
61 % With bis(tri-t-butylphosphine)palladium(0); potassium carbonate In tetrahydrofuran; water Reflux; 84 Synthesis Example 84 Im-6-6 (15 g, 28.6 mmol) and im-a-5 (11.1 g, 30 mmol) were added to 300 ml of THF and stirred and refluxed. Thereafter, potassium carbonate (11.8g, 85.7mmol) was dissolved in 100 ml of water, and after stirring sufficiently, bis(tri-tert-butylphosphine)palladium(0) (0.1g, 0.3mmol) was added. After reacting for 2 hours, it was cooled to room temperature, and the organic layer and the water layer were separated, and the organic layer was distilled. 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 12.7 g of compound 84. (yield 61%)
  • 31
  • [ 1357634-60-6 ]
  • [ 2922951-27-5 ]
  • [ 2922947-03-1 ]
YieldReaction ConditionsOperation in experiment
69 % With bis(tri-t-butylphosphine)palladium(0); potassium carbonate In tetrahydrofuran; water Reflux; 86 Synthesis Example 86 Im-6-8 (15 g, 30.9 mmol) and im-a-5 (12 g, 32.5 mmol) were added to 300 ml of THF and stirred and refluxed. Thereafter, potassium carbonate (12.8g, 92.8mmol) was dissolved in 100 ml of water, and after stirring sufficiently, bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.3mmol) was added. After reacting for 5 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 14.8 g of compound 86. (yield 69%)
  • 32
  • [ 1357634-60-6 ]
  • [ 2922950-64-7 ]
  • [ 2922946-97-0 ]
YieldReaction ConditionsOperation in experiment
67 % With bis(tri-t-butylphosphine)palladium(0); potassium carbonate In tetrahydrofuran; water Reflux; 20 Synthesis Example 20 Im-2-8 (15 g, 33.4 mmol) and im-a-5 (13 g, 35.1 mmol) were added to 300 ml of THF and stirred and refluxed. Thereafter, potassium carbonate (13.9g, 100.3mmol) was dissolved in 100 ml of water, and after stirring sufficiently, bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.3mmol) 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 14.7 g of Compound 20. (Yield 67%)
  • 33
  • [ 1357634-60-6 ]
  • [ 2922950-65-8 ]
  • [ 2922948-92-1 ]
YieldReaction ConditionsOperation in experiment
72 % With bis(tri-t-butylphosphine)palladium(0); potassium carbonate In tetrahydrofuran; water Reflux; 21 Synthesis Example 21 Im-2-9 (15 g, 28.6 mmol) and im-a-5 (11.1 g, 30 mmol) were added to 300 ml of THF and stirred and refluxed. Thereafter, potassium carbonate (11.8g, 85.7mmol) was dissolved in 100 ml of water, and after stirring sufficiently, bis(tri-tert-butylphosphine)palladium(0) (0.1g, 0.3mmol) 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 15 g of Compound 21. (Yield 72%)
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