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Chemical Structure| 1246308-85-9
Chemical Structure| 1246308-85-9
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Product Details of [ 1246308-85-9 ]

CAS No. :1246308-85-9 MDL No. :N/A
Formula : C18H11NO Boiling Point : -
Linear Structure Formula :- InChI Key :DERKMBVPWKXOHM-UHFFFAOYSA-N
M.W : 257.29 Pubchem ID :58489692
Synonyms :

Safety of [ 1246308-85-9 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338 UN#:
Hazard Statements:H302-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 1246308-85-9 ]

* 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 [ 1246308-85-9 ]

[ 1246308-85-9 ] Synthesis Path-Downstream   1~79

  • 1
  • [ 66611-15-2 ]
  • [ 1246308-85-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: acetic acid / ethanol / 8 h / 20 °C 1.2: polyphosphoric acid / 1 h / 120 °C 1.3: Cooling with ice 2.1: acetic acid / Reflux
Multi-step reaction with 2 steps 1: phenylhydrazine / ethanol; water; acetic acid 2: acetic acid; sodium chloride / water
  • 2
  • [ 626-00-6 ]
  • [ 1246308-85-9 ]
  • [ 1338919-72-4 ]
YieldReaction ConditionsOperation in experiment
48% With potassium carbonate;copper; In Tridecane; at 145 - 185℃; for 72h; Synthesis example B7: Synthesis of 1 ,3-bis(12-(12H-benzofuranyl[3,2-a])carbazolyl)benzene (compound 7); The suspension of compound 6 (1.70 g, 6.6 mmol), 1 ,3-diiodobenzene (98%; 1.1 1 g, 3.3 mmol), potassium carbonate (2.28 g, 17 mmol) and copper powder (0.17 g, 2.6 mmol) in n-tridecane (3 ml) is heated to 145C and stirred for 48 h. Then compound 6 (0.5 g) is added and the reaction temperature is increased to 185C and the mixture is stirred for a further 24 h. The mixture is cooled to room temperature and diluted with n- heptane, filtered and washed with n-heptane. The residue is then washed with warm distilled water to free it of salts and dried at 65C under reduced pressure. LC (Si02, 1 :4 methylene chloride/cyclohexane) gives the product 7 (0.89 g, 48% yield).1H NMR (CD2CI2, 400 MHz): «5 = 8.21 (d, 2H), 8.12 (d, 2H), 7.97-8.07 (m, 3H), 7.75 (s, 1 H), 7.58 (dd, 4H), 7.40 (d, 2H) 7.35 (d, 2H), 7.25-7.32 (m, 4H), 7.12 (dd, 2H), 6.23 (d, 2H).
  • 3
  • [ 3616-56-6 ]
  • [ 1088487-06-2 ]
  • [ 1246308-85-9 ]
YieldReaction ConditionsOperation in experiment
62.2% With acetic acid;Reflux; Synthesis example B6: Synthesis of 12H-benzofuranyl[3,2-a]carbazole (compound 6); (6); Compound 5 (2.8 g, 1 eq.) is added to acetic acid (30 ml) and heated to reflux. (Dimethylamino)acetaldehyde diethyl acetal (95percent; 20.3 g, 10 eq.) is added dropwise in portions to the solution. The reaction is stirred at reflux overnight. Then further (dimethylamino)acetaldehyde diethyl acetal (95percent; 2.0 g) is added and stirred further at reflux after 3 h. Subsequently, the flask contents are diluted with CH2CI2 at room temperature and washed in a separating funnel with distilled water and NaCI (saturated). Organic phase is dried with Na2S04 and concentrated. LC (Si02, 15:85 ethyl acetate/cyclohexane) gives the product 6 (1 .92 g, 62.2percent yield).1 H NMR (CD2CI2, 400 MHz): "5 = 8.88 (br s, 1 H), 8.16 (d, 1 H), 8.12 (d, 2H), 7.66 (d, 1 H), 7.62 (d, 1 H), 7.42-7.53 (m, 4H), 7.31 (dd, 1 H).
62.2% With acetic acid; sodium chloride; In water; Synthesis Example B6Synthesis of 12H-benzofuranyl[3,2-a]carbazole (compound 6)Compound 5 (2.8 g, 1 eq.) is added to acetic acid (30 ml) and heated to reflux. (Dimethylamino)acetaldehyde diethyl acetal (95percent; 20.3 g, 10 eq.) is added dropwise in portions to the solution.The reaction is stirred at reflux overnight.Then further (dimethylamino)acetaldehyde diethyl acetal (95percent; 2.0 g) is added and stirred further at reflux after 3 h.Subsequently, the flask contents are diluted with CH2Cl2 at room temperature and washed in a separating funnel with distilled water and NaCl (saturated).Organic phase is dried with Na2SO4 and concentrated. LC (SiO2, 15:85 ethyl acetate/cyclohexane) gives the product 6 (1.92 g, 62.2percent yield).1H NMR (CD2Cl2, 400 MHz): delta=8.88 (br s, 1H), 8.16 (d, 1H), 8.12 (d, 2H), 7.66 (d, 1H), 7.62 (d, 1H), 7.42-7.53 (m, 4H), 7.31 (dd, 1H).
  • 4
  • [ 5211-62-1 ]
  • [ 1246308-85-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: N,N-dimethyl-formamide / 24 h / 80 °C 1.2: 0 °C 1.3: Cooling with ice 2.1: acetic acid / ethanol / 8 h / 20 °C 2.2: polyphosphoric acid / 1 h / 120 °C 2.3: Cooling with ice 3.1: acetic acid / Reflux
Multi-step reaction with 3 steps 1: boron tribromide / dichloromethane; N,N-dimethyl-formamide 2: phenylhydrazine / ethanol; water; acetic acid 3: acetic acid; sodium chloride / water
  • 5
  • [ 626-00-6 ]
  • [ 1246308-85-9 ]
  • copper [ No CAS ]
  • [ 1338919-72-4 ]
YieldReaction ConditionsOperation in experiment
48% With potassium carbonate In Tridecane S.B.7 Synthesis of 1,3-bis(12-(12H-benzofuranyl[3,2-a])carbazolyl)benzene (compound 7) Synthesis Example B7 Synthesis of 1,3-bis(12-(12H-benzofuranyl[3,2-a])carbazolyl)benzene (compound 7) The suspension of compound 6 (1.70 g, 6.6 mmol), 1,3-diiodobenzene (98%; 1.11 g, 3.3 mmol), potassium carbonate (2.28 g, 17 mmol) and copper powder (0.17 g, 2.6 mmol) in n-tridecane (3 ml) is heated to 145° C. and stirred for 48 h. Then compound 6 (0.5 g) is added and the reaction temperature is increased to 185° C. and the mixture is stirred for a further 24 h. The mixture is cooled to room temperature and diluted with n-heptane, filtered and washed with n-heptane. The residue is then washed with warm distilled water to free it of salts and dried at 65° C. under reduced pressure. LC (SiO2, 1:4 methylene chloride/cyclohexane) gives the product 7 (0.89 g, 48% yield). 1H NMR (CD2Cl2, 400 MHz): δ=8.21 (d, 2H), 8.12 (d, 2H), 7.97-8.07 (m, 3H), 7.75 (s, 1H), 7.58 (dd, 4H), 7.40 (d, 2H) 7.35 (d, 2H), 7.25-7.32 (m, 4H), 7.12 (dd, 2H), 6.23 (d, 2H).
YieldReaction ConditionsOperation in experiment
82% With triphenylphosphine In 1,2-dichloro-benzene at 180℃; for 24h; 2 Synthesis method of Sub 2-II-1 General procedure: Sub 2-I-1 (99 g, 323 mmol) was added to a round bottom flask, Add PPh3 (218 g, 808 mmol) and o-Dichlorobenzene (1.0 L). Then, the mixture is heated under reflux at 180 ° C for 24 hours. When the reaction is completed, cool to room temperature and concentrate. ConcentratedThe resulting compound was purified by silica column and recrystallized to obtain the product Sub 2-II-1 (70 g, 80%).
82% With triphenylphosphine In 1,2-dichloro-benzene at 180℃; for 24h; 2 Synthesis Method of Sub 2-II-1 General procedure: To a round bottom flask were added Sub 2-I-1 (99 g, 323 mmol), PPh3(218 g, 808 mmol) and o-Dichlorobenzene (1.0 L). Then, the mixture was heated and refluxed at 180° C. for 24 hours. When the reaction was completed, the reaction product was cooled to room temperature and concentrated. The resulting compound was purified by column chromatography on silica gel and recrystallized to obtain the product Sub 2-II-1 (70 g, 80%).
82% With triphenylphosphine In 1,2-dichloro-benzene at 180℃; for 24h; 1.2 Synthesis of Sub 2-II-1 General procedure: To the round bottom flask, add Sub 2-I-1 (99g, 323mmol), PPh3 (218g, 808mmol), and o-Dichlorobenzene (1.0L).Then, the mixture was heated to reflux for 24 hours at 180 ° C.Upon completion of the reaction, cool to room temperature and concentrate.The resulting compound was concentrated to silica column and recrystallized to obtain the product Sub 2-II-1 (70 g, 80%).
82% With triphenylphosphine In 1,2-dichloro-benzene at 180℃; for 24h; 1.2 Synthesis of Sub 2-II-1 General procedure: To the round bottom flask, add Sub 2-I-1 (99g, 323mmol), PPh3 (218g, 808mmol), and o-Dichlorobenzene (1.0L).Then, the mixture was heated to reflux for 24 hours at 180 ° C.Upon completion of the reaction, cool to room temperature and concentrate. The concentrated product is silica columnAnd recrystallized to obtain the product Sub 2-II-1 (70 g, 80%).
82% With triphenylphosphine In 1,2-dichloro-benzene at 180℃; for 24h; 1.2 Synthesis of Sub 2-II-1 General procedure: Round bottom flask Sub 2-I-1 (99g, 323mmol),Add PPh3 (218g, 808mmol) and o-Dichlorobenzene (1.0L).Then, the mixture was heated to reflux for 24 hours at 180 ° C.Upon completion of the reaction, cool to room temperature and concentrate.The resulting compound was concentrated to silica column and recrystallized to obtain the product Sub 2-II-1 (70 g, 80%).
82% With triphenylphosphine In 1,2-dichloro-benzene at 180℃; for 24h; 1.2.4.2 (2) Synthesis of Sub 2-II-1 General procedure: In a round bottom flask, Sub 2-I-1 (99 g, 323 mmol), PPh3(218 g, 808 mmol), ando-Dichlorobenzene (1.0 L) are added.Then, the mixture was heated to reflux for 24 hours at 180 ° C.Upon completion of the reaction, cool to room temperature and concentrate.The resulting compound was concentrated to silica column and recrystallized to obtain the product Sub 2-II-1 (70 g, 80%).
44% With (bis(tricyclohexyl)phosphine)palladium(II) dichloride; caesium carbonate; Trimethylacetic acid In N,N-dimethyl acetamide at 120℃; for 10h; Inert atmosphere; 8.2 (2) Synthesis of Inter2-62 General procedure: Take a 100 ml three-necked flask, put it in the stir bar and the upper connection reflux tube, and fill it with nitrogen after drying, Inter1-62 (3.59g, 0.1mol), dichlorobis(tricyclohexylphosphine)palladium(II) (PdCl2(PCy3)2, 5mmol), pivalic acid (t-BuCO2H, 0.2mol), cesium carbonate (Cs2CO3, 0.2mol) and dimethylacetamide (30ml), stirred at 120 degrees celsius for 10 hours, after the reaction was completed, it was cooled to room temperature, the reaction system was concentrated, and the crude product was purified by chromatography (ethyl acetate/hexane, 1/10) to obtain Inter2-62 (1.52 g, yield 47%).
22.48% With triethyl phosphite for 10h; Reflux; 5 Preparation of Compound A-2 General procedure: 31 g (124.3 mmol) of Compound A-1 and 300 mL of triethyl phosphite were added thereto, followed by stirring under reflux. After 10 hours, the mixture was cooled to room temperature, and the organic solvent was distilled off under reduced pressure. Distilled water was added and extracted with EA. Dried over magnesium sulfate and distilled under reduced pressure.Compound A-2 by column separation 18 g (82.84 mmol, 66.81%) was obtained.
22.48% With triethyl phosphite for 10h; Reflux; 5 Preparation of compound A-2 General procedure: Compound A-1 31 g (124.3 mmol) and triethyl phosphite 300 mL were added and stirred under reflux. After 10 hours, the mixture was cooled to room temperature and the organic solvent was distilled off under reduced pressure. Distilled water was added and extracted with EA. It was dried over magnesium sulfate and distilled under reduced pressure. Column separation was performed to obtain 18 g (82.84 mmol, 66.81%) of compound A-2
With triphenylphosphine In 1,2-dichloro-benzene at 170 - 190℃; Inert atmosphere; 11 General procedure: (2) In a 250 mL three-necked flask, under the protection of nitrogen,Add 0.02mol of intermediate S1,Dissolve with 100mL o-dichlorobenzene,Adding 0.03mol of triphenylphosphine,Stir the reaction at 170 ~ 190°C for 12 ~ 16h.After the reaction was completed, the solution was cooled to room temperature, filtered, and the filtrate was rotary evaporated under reduced pressure, and passed through a neutral silica gel column to obtain intermediate D1.HPLC purity 97.2%, yield 77.8%;

  • 7
  • [ 1246308-85-9 ]
  • 3-(dibenzo[b,d]furan-2-yl)-2-fluorobenzonitrile [ No CAS ]
  • C37H20N2O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
31% Stage #1: 12H-benzofuro[3,2-a]carbazole With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 2h; Stage #2: 3-(dibenzo[b,d]furan-2-yl)-2-fluorobenzonitrile In N,N-dimethyl-formamide; mineral oil at 150℃; 16 Synthesis Example 16: Synthesis of Compound 459 Compound 459 was synthesized in the same manner as in Synthesis Example 1 except for the following:I) In the synthesis of intermediate (1), 3-bromo-2-fluorobenzonitrile was used in place of 4-bromo-3-fluorobenzonitrile, andIi) In the synthesis of compound 3, the intermediate (6) was used in place of the carbazole and the reaction temperature was changed to 150 ° C (yield 31%).20 ml of N, N-dimethylformamide was slowly added to a solution of 1.9 g (47.8 mmol) of sodium hydride (NaH) at 0 ° C,(60% in mineral oil), and the resulting mixture was stirred for 10 minutes. Then, 8 g (47.8 mmol) of carbazole was dissolved30 ml of N, N-dimethylformamide, and the resulting mixture was slowly added to the above reaction solution and stirred at room temperature2 hours. A mixture of 90 ml of N, N-dimethylformamide and 10.9 g (38.0 mmol) of intermediate (1) was added to the aboveReaction solution. The resulting mixture was heated to 120 deg.] C and reflux. When the reaction was complete, the reaction solution was added to methanol / waterTo obtain a precipitate, and the precipitate was filtered and washed with methanol. The resultant obtained from the above procedure was dissolved in heatIn toluene and filtered through silica gel to give the filtrate. The filtrate was concentrated to give a solid and the solid was recrystallized(Dichloromethane / methanol, ethyl acetate) twice to yield compound 3 (8.9 g, 20.5 mmol, 54% yield).
  • 8
  • [ 1073-06-9 ]
  • [ 1246308-85-9 ]
  • C24H14BrNO [ No CAS ]
YieldReaction ConditionsOperation in experiment
73% Stage #1: 12H-benzofuro[3,2-a]carbazole With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 3h; Stage #2: 3-fluorobromobenzene In N,N-dimethyl-formamide; mineral oil at 150℃; for 22h; 1.1 (1) Synthesis of Intermediate 1 3 grams (g) (73.46 millimoles, mmol) of NaH (60% in mineral oil) was added into a well-dried 500-ml round-bottom flask (RBF) and 200 milliliters (ml) of dimethylformamide (DMF) was added thereto. The mixture was stirred at a temperature of 0° C. under a nitrogen atmosphere. 18 g (69.96 mmol) of 12H-benzofuro[3,2-a]carbazole was slowly dissolved in 100 ml of DMF and added to the mixture. The resultant was heated to room temperature and stirred for 3 hours. 19.6 g (112 mmol) of 1-bromo-3-fluorobenzene was slowly added to the reaction mixture. The reaction temperature was raised to 150° C., and the resultant substance was stirred for 22 hours. A solid product was extracted by using methylene chloride (MC) and was dried by using MgSO4. The solvent was concentrated under reduced pressure. A solution dissolved in hot toluene was filtered through a thin plug of silica, and the filtrate was concentrated under reduced pressure. A precipitate was formed upon treatment with MC/methanol mixture and the resultant was passed through a filtering paper. The obtained solid was dried in a vacuum oven to obtain 21 g (73%) of Intermediate 1.
  • 9
  • [ 1246308-85-9 ]
  • [ 1361227-58-8 ]
  • C43H25NO [ No CAS ]
YieldReaction ConditionsOperation in experiment
74.2% With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate; In toluene; at 105℃; for 24h;Inert atmosphere; In a 250ml three-vial bottle,Under nitrogen protection,0.01 mol of <strong>[1361227-58-8]3-bromo-9,9'-spirobifluorene</strong> was added,0.012 mole of intermediate B1,Mix 150ml of toluene,Then add 0.03mol of sodium tert-butoxide,5×10-5 mol Pd2(dba)3,5×10-5 mol of tri-tert-butylphosphine,Heat to 105C,Reflux reaction for 24 hours,Sampling point plate, showing no bromine residue, complete reaction; naturally cooled to room temperature, filtered, the filtrate was evaporated under reduced pressure (-0.09MPa, 85 C), over neutral silica gel column to obtain the target product,HPLC purity 99.4%, yield 74.2%;
  • 10
  • [ 1246308-85-9 ]
  • 3,3'-dibromo-9,9'-spirobi[fluorene] [ No CAS ]
  • C52H33NO [ No CAS ]
YieldReaction ConditionsOperation in experiment
68.8% With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In toluene at 105℃; for 24h; Inert atmosphere; 20 Example 20: Synthesis of Compound 124: In a 250 ml three-necked flask, under the protection of nitrogen, 0.01 mol of 3,3'-dibromo-9,9'-spirobifluorene,0.024 mol of intermediate T1, and 150 ml of toluene were added and mixed, and then 0.04 mol of sodium tert-butoxide was added. × 10. 1-4molPd2(DBA). 3,. 1 × 10-4mol butylphosphine, was heated to 105 deg.] C, the reaction was refluxed for 24 hours, and sampling showed no remaining bromideI, the reaction was complete; natural cooling At room temperature, the mixture was filtered, and the filtrate was evaporated under reduced pressure (-0.09 MPa, 85°C). Thetarget product was obtained ona neutral silica gel column. HPLC purity was 99.3%, and the yield was 68.8%.
  • 11
  • [ 1246308-85-9 ]
  • [ 864377-22-0 ]
  • C40H25N3O [ No CAS ]
YieldReaction ConditionsOperation in experiment
62.2% With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In toluene for 24h; Inert atmosphere; Reflux; 3 Example 3: Synthesis of Compound 15: 250ml four-necked flask, under a nitrogen atmosphere,Add 0.01 mol of raw material A3, 0.025 mol of raw material B2,0.04 mol of sodium tert-butoxide, 2 x 10-4 mol of Pd2(dba)3,2×10-4 mol of tri-tert-butylphosphine, 150 ml of toluene,Heat reflux for 24 hours, sample the plate, reaction is complete;Cool naturally, filter, rotate the filtrate, pass the silica gel column,The target product 15 was obtained with a purity of 97.7%.Yield 62.2%.
  • 12
  • [ 1246308-85-9 ]
  • 2-bromo-9,9-dimethyl-10-(biphenyl-4-yl)acridane [ No CAS ]
  • C45H32N2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
73.9% With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In toluene at 105℃; for 24h; Inert atmosphere; 10 Example 10: Synthesis of Compound 33: In a 250ml three-neck bottle,Under the protection of nitrogen,Add 0.01 mol of intermediate C3,0.012 mol of raw material F3,150 ml of toluene was mixed and mixed.Then 0.03 mol of sodium t-butoxide was added,5×10-5 mol Pd2(dba)3,5 x 10-5 mol of tri-tert-butylphosphine,Heat to 105 ° C, reflux reaction for 24 hours,Sampling plate, showing no bromine residue remaining, complete reaction;Naturally cooled to room temperature, filtered, and the filtrate was evaporated to dryness under reduced pressure (-0.09 MPa, 85 ° C).The target product was obtained, HPLC purity: 99.1%, yield 73.9%
  • 13
  • [ 86-76-0 ]
  • [ 1246308-85-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: tetrakis-(triphenylphosphine)-palladium; sodium hydroxide / tetrahydrofuran; lithium hydroxide monohydrate / 4 h / 70 °C 2: triphenylphosphine / 1,2-dichloro-benzene / 24 h / 180 °C
Multi-step reaction with 2 steps 1: potassium carbonate; tetrakis-(triphenylphosphine)-palladium / tetrahydrofuran; lithium hydroxide monohydrate / 8 h / Inert atmosphere; Reflux 2: triphenylphosphine / 1,2-dichloro-benzene / 24 h / Reflux
Multi-step reaction with 2 steps 1.1: anhydrous sodium carbonate / toluene; ethanol; lithium hydroxide monohydrate / 1 h / Inert atmosphere 1.2: 15 h / Reflux 2.1: triphenylphosphine / 1,2-dichloro-benzene / 15 h / 170 °C / Inert atmosphere
Multi-step reaction with 3 steps 1.1: tetrahydrofuran / 0.5 h / -78 °C 1.2: 1 h / -78 °C 1.3: 20 °C 2.1: tetrakis-(triphenylphosphine)-palladium; potassium carbonate / lithium hydroxide monohydrate / 8 h / 110 °C 3.1: triethyl phosphite / 24 h / 180 °C / Inert atmosphere

  • 14
  • [ 1246308-82-6 ]
  • [ 1246308-85-9 ]
YieldReaction ConditionsOperation in experiment
82% With triphenylphosphine In 1,2-dichloro-benzene at 180℃; for 24h; 5.2 (2) Synthesis Method of Sub 1-8-2 Sub 1-8-1 (43 g, 110 mmol), PPh3 (72 g, 276 mmol), and o-Dichlorobenzene (350 mL) were added into a round bottom flask, then, heated and refluxed at 180° C. for 24 hours. When the reaction was completed, the reaction product was cooled to room temperature and concentrated. The concentrate was passed through silica gel column, and then recrystallized to obtain 23 g of the product Sub 1-8-2 (Yield: 82%).
75% With triphenylphosphine In 1,2-dichloro-benzene for 24h; Reflux; 1.2 2) Preparation of Compound A-2 A two-necked flask was charged with Compound A-1 (18.0 g, 62.2 mmol)Triphenylphosphine (12.9 g, 93.3 mmol), And o-dichlorobenzene (180 mL) were added thereto, and the mixture was stirred under reflux for 24 hours. After the reaction was completed, the reaction mixture was cooled to room temperature,The solvent was removed by distillation under reduced pressure and extracted with CH2Cl2. The extract was dried over MgSO4, filtered, and concentrated. The sample was purified by silica gel column chromatography to obtain Compound A-2 (12.0 g, yield 75%
75% With triethyl phosphite at 180℃; for 24h; Inert atmosphere; 2.4. Synthesis of 12H-benzofuro[3,2-a]carbazole (DBF-INFUR) A mixture of 2-(2-nitrophenyl)dibenzo[b,d]furan (DBF-Ph-N, 6g,20.76 mmol), triethyl phospite (P(OEt)3, 70 ml) and o-dichlorobenzene(70 ml) was refluxed at 180 °C for 24 h under inert condition. Aftercompletion of the reaction, reaction mixture was concentrated, andcrude mixture was separated by using silica column (n-Hexane anddichloromethane).Yield: 75%; Pale white solid; 1H NMR (500 MHz, CDCl3) 8.55 (S,1H), 8.14-8.16 (d, J 8.5 Hz, 1H), 8.11-8.13 (d, J 8 Hz, 1H),8.06-8.08 (d, J 8 Hz, 1H), 7.66-7.67 (d, J 8 Hz, 1H), 7.58-7.60 (d, J 8 Hz, 1H) 7.42-7.51 (m, 5H), 7.30-7.33 (t, J 7.5 Hz, 1H).
73% With triphenylphosphine In 1,2-dichloro-benzene at 180℃; for 24h; 1.1.5 Synthesis Method of Sub 1-23-2 After Sub 1-23-1 (223 g, 770.9 mmol), PPh3 (505.47 g, 1927.1 mmol), o-dichlorobenzene (3.8 L) were placed in a round bottom flask, the mixture was heated at 180° C. for 24 hours under reflux. When the reaction was completed, the reaction product was cooled to a room temperature and concentrated. Then, the concentrate was applied to silicagel column and recrystallized to obtain the product Sub 1-23-2 (144.78 g, 73%).
73% With triphenylphosphine In 1,2-dichloro-benzene at 180℃; for 24h; 1.1.5 Synthesis Method of Sub 1-23-2 After Sub 1-23-1 (223 g, 770.9 mmol), PPh3 (505.47 g, 1927.1 mmol), o-dichlorobenzene (3.8 L) were placed in a round bottom flask, the mixture was heated at 180° C. for 24 hours under reflux. When the reaction was completed, the reaction product was cooled to a room temperature and concentrated. Then, the concentrate was applied to silicagel column and recrystallized to obtain the product Sub 1-23-2 (144.78 g, 73%).
With triphenylphosphine In 1,2-dichloro-benzene at 170℃; for 15h; Inert atmosphere; III.2 (2) In a 100ml three-necked flask, add 0.03mol of intermediate P1-1 and 0.036mol of triphenylphosphine under nitrogen protection, dissolve with 50ml of o-dichlorobenzene, heat to 170 ° C, react for 15 hours, sampling point Plate, reaction is complete. Allow to cool, filter, and spin the filtrate through a silica gel column to obtain intermediate P2-1.
With triphenylphosphine In 1,2-dichloro-benzene at 180℃;

  • 15
  • [ 1246308-85-9 ]
  • C54H36N2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: N-Bromosuccinimide / dichloromethane / 4 h / 20 °C 2: sodium t-butanolate; tri-tert-butyl phosphine; tris-(dibenzylideneacetone)dipalladium(0) / toluene / 8 h / 110 °C 3: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / N,N-dimethyl-formamide / 8 h / 110 °C 4: tetrakis(triphenylphosphine) palladium(0); sodium hydroxide / tetrahydrofuran; water / 8 h / 110 °C 5: sodium t-butanolate; tri-tert-butyl phosphine; tris-(dibenzylideneacetone)dipalladium(0) / toluene / 3 h / 110 °C
  • 16
  • [ 1246308-85-9 ]
  • C67H44N2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: N-Bromosuccinimide / dichloromethane / 4 h / 20 °C 2: sodium t-butanolate; tri-tert-butyl phosphine; tris-(dibenzylideneacetone)dipalladium(0) / toluene / 8 h / 110 °C 3: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / N,N-dimethyl-formamide / 8 h / 110 °C 4: tetrakis(triphenylphosphine) palladium(0); sodium hydroxide / tetrahydrofuran; water / 8 h / 110 °C 5: sodium t-butanolate; tri-tert-butyl phosphine; tris-(dibenzylideneacetone)dipalladium(0) / toluene / 3 h / 110 °C
  • 17
  • [ 1246308-85-9 ]
  • 6-bromo-12H-benzofuro[3,2-a]carbazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% With NBS at 20℃; for 4h; 1.1.5 Synthesis Method of Sub 1-23-3 After Sub 1-23-2 (145 g, 563.6 mmol), N-bromosuccinimide (100.31 g, 563.6 mmol), m chloride (2.8 L) were placed in a round bottom flask, the mixture was stirred at a room temperature for 4 hours. When the reaction was completed, distilled water was added and the reaction product was extracted with methylene chloride and water. Then, the organic layer was dried with MgSO4 and concentrated. Then, the concentrate was recrystallized with methylene chloride and hexane to obtain the product Sub 1-23-3 (164.83 g, 87%).
87% With NBS at 20℃; for 4h; 1.1.5 Synthesis Method of Sub 1-23-3 After Sub 1-23-2 (145 g, 563.6 mmol), N-bromosuccinimide (100.31 g, 563.6 mmol), m chloride (2.8 L) were placed in a round bottom flask, the mixture was stirred at a room temperature for 4 hours. When the reaction was completed, distilled water was added and the reaction product was extracted with methylene chloride and water. Then, the organic layer was dried with MgSO4 and concentrated. Then, the concentrate was recrystallized with methylene chloride and hexane to obtain the product Sub 1-23-3 (164.83 g, 87%).
86% With NBS In dichloromethane at 0 - 20℃; for 8h; 1.3 3) Preparation of Compound A-3 In a two-necked flask, Compound A-2 (12.0 g, 46.6 mmol) was dissolved in CH2Cl2 (240 mL), NBS (9.1 g, 51.3 mmol) was slowly added at 0 ° C,The mixture was stirred at room temperature for 8 hours. After completion of the reaction, The reaction solution was transferred to a separatory funnel, washed with water (150 mL)And extracted with ethyl acetate. The extract was dried with MgSO4,After filtration and concentration,The sample was purified by silica gel column chromatography to obtain Compound A-3 (13.5 g, yield 86%
80% With NBS In N,N-dimethyl-formamide at 20℃; for 8h;
70% With NBS In dichloromethane at 20℃; for 4h; 5.3 (3) Synthesis Method of Sub 1-8-3 Sub 1-8-2 (23 g, 89 mmol), N-Bromosuccinimide (16 g, 89 mmol), and Methylene chloride (300 mL) were added into a round bottom flask, then, stirred at room temperature for 4 hours. When the reaction was completed, distilled water was added. The resultant was extracted with Methylene chloride and water. The organic layer was dried with MgSO4 and concentrated. The concentrate was recrystallized with Methylene chloride and Hexane to obtain 21 g of the product Sub 1-8-3 (Yield: 70%).

  • 18
  • [ 1246308-85-9 ]
  • C24H14BrNO [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: NBS / dichloromethane / 4 h / 20 °C 2: sodium tertiary butoxide; tri-tert-butyl phosphine; tris-(dibenzylideneacetone)dipalladium(0) / toluene / 8 h / 110 °C
Multi-step reaction with 2 steps 1: NBS / 4 h / 20 °C 2: tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium tertiary butoxide / toluene / 8 h / 110 °C
  • 19
  • [ 1246308-85-9 ]
  • C30H26BNO3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: NBS / dichloromethane / 4 h / 20 °C 2: sodium tertiary butoxide; tri-tert-butyl phosphine; tris-(dibenzylideneacetone)dipalladium(0) / toluene / 8 h / 110 °C 3: palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; anhydrous potassium acetate / N,N-dimethyl-formamide / 8 h / 110 °C
Multi-step reaction with 3 steps 1: NBS / 4 h / 20 °C 2: tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium tertiary butoxide / toluene / 8 h / 110 °C 3: palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; anhydrous potassium acetate / N,N-dimethyl-formamide / 8 h / 110 °C
  • 20
  • [ 1246308-85-9 ]
  • C30H18BrNO [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: N-Bromosuccinimide / dichloromethane / 4 h / 20 °C 2: sodium t-butanolate; tri-tert-butyl phosphine; tris-(dibenzylideneacetone)dipalladium(0) / toluene / 8 h / 110 °C 3: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / N,N-dimethyl-formamide / 8 h / 110 °C 4: tetrakis(triphenylphosphine) palladium(0); sodium hydroxide / tetrahydrofuran; water / 8 h / 110 °C
  • 21
  • [ 5570-19-4 ]
  • [ 1246308-85-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: tetrakis-(triphenylphosphine)-palladium; sodium hydroxide / tetrahydrofuran; lithium hydroxide monohydrate / 4 h / 70 °C 2: triphenylphosphine / 1,2-dichloro-benzene / 24 h / 180 °C
Multi-step reaction with 2 steps 1: potassium carbonate; tetrakis-(triphenylphosphine)-palladium / tetrahydrofuran; lithium hydroxide monohydrate / 8 h / Inert atmosphere; Reflux 2: triphenylphosphine / 1,2-dichloro-benzene / 24 h / Reflux
Multi-step reaction with 2 steps 1.1: anhydrous sodium carbonate / toluene; ethanol; lithium hydroxide monohydrate / 1 h / Inert atmosphere 1.2: 15 h / Reflux 2.1: triphenylphosphine / 1,2-dichloro-benzene / 15 h / 170 °C / Inert atmosphere
  • 22
  • [ 1246308-85-9 ]
  • C31H20BrNO2S [ No CAS ]
  • C49H30N2O3S [ No CAS ]
YieldReaction ConditionsOperation in experiment
56.6% With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In toluene for 24h; Inert atmosphere; Reflux; 4 Example 4 Compound C23 Take a 250ml three-necked bottle under a nitrogen atmosphere.Add 0.01 mol of 10-(3-bromophenyl)-acridium stilbene sulfone,0.02 mol of compound R2, 0.03 mol of sodium t-butoxide, 1 x 10-4 mol of Pd2 (dba) 3,1×10-4 mol of tri-tert-butylphosphine,150ml of toluene, heated to reflux for 24 hours, sampling the plate, and naturally cooled,Filtration, the filtrate is steamed, passed through a silica gel column,The target product was obtained with a purity of 98.5% and a yield of 56.6%.
  • 23
  • [ 1246308-85-9 ]
  • C45H27N5O [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: caesium carbonate / dimethyl sulfoxide / 15 h / Inert atmosphere 2: caesium carbonate; palladium diacetate; tricyclohexylphosphine tetrafluoroborate / o-xylene / 2 h / Inert atmosphere; Reflux 3: tin(II) chloride dihdyrate; hydrogenchloride / ethanol; water / 10 h / 60 °C / Inert atmosphere 4: palladium diacetate; tri-tert-butyl phosphine; sodium t-butanolate / toluene / 12 h / 110 °C / Inert atmosphere
  • 24
  • [ 1246308-85-9 ]
  • C38H20N4O [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: caesium carbonate / dimethyl sulfoxide / 15 h / Inert atmosphere 2: caesium carbonate; palladium diacetate; tricyclohexylphosphine tetrafluoroborate / o-xylene / 2 h / Inert atmosphere; Reflux 3: tin(II) chloride dihdyrate; hydrogenchloride / ethanol; water / 10 h / 60 °C / Inert atmosphere 4: caesium carbonate; dmap / dimethyl sulfoxide / 3 h / 100 °C / Inert atmosphere
  • 25
  • [ 1246308-85-9 ]
  • C24H12N2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: caesium carbonate / dimethyl sulfoxide / 15 h / Inert atmosphere 2: caesium carbonate; palladium diacetate; tricyclohexylphosphine tetrafluoroborate / o-xylene / 2 h / Inert atmosphere; Reflux 3: tin(II) chloride dihdyrate; hydrogenchloride / ethanol; water / 10 h / 60 °C / Inert atmosphere
  • 26
  • [ 1246308-85-9 ]
  • C24H12N2O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: caesium carbonate / dimethyl sulfoxide / 15 h / Inert atmosphere 2: caesium carbonate; palladium diacetate; tricyclohexylphosphine tetrafluoroborate / o-xylene / 2 h / Inert atmosphere; Reflux
  • 27
  • [ 1246308-85-9 ]
  • [ 2106-49-2 ]
  • C24H13ClN2O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% With caesium carbonate; In dimethyl sulfoxide; for 15h;Inert atmosphere; Under a nitrogen atmosphere, into a 500 mL three-necked flask,12.8 g of the compound of formula (C-1) (50 mmol) was added,8.8 g of <strong>[2106-49-2]3-chloro-2-fluoronitrobenzene</strong> (50 mmol) (compound represented by formula (E-1)),19.5 g of cesium carbonate (60 mmol), dimethyl sulfoxide 200 mL, and reacted for 15 hours.Extract with toluene, remove the solvent by rotary evaporation.Obtained through the silica gel column14.8gSolid intermediate 3-1(yield 72%);
  • 28
  • [ 1246308-85-9 ]
  • 6-(9H-carbazol-9-yl)-12H-benzofuro[3,2-a]carbazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N-Bromosuccinimide / dichloromethane / 8 h / 0 - 20 °C 2: bis(tri-t-butylphosphine)palladium(0); sodium t-butanolate / toluene / 12 h / Inert atmosphere; Reflux
Multi-step reaction with 2 steps 1: N-Bromosuccinimide / N,N-dimethyl-formamide / 8 h / 20 °C 2: potassium <i>tert</i>-butylate; XPhos; tris-(dibenzylideneacetone)dipalladium(0) / o-xylene / 6 h / Reflux
  • 29
  • [ 1246308-85-9 ]
  • C44H26N4O [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: N-Bromosuccinimide / dichloromethane / 8 h / 0 - 20 °C 2: bis(tri-t-butylphosphine)palladium(0); sodium t-butanolate / toluene / 12 h / Inert atmosphere; Reflux 3: bis(tri-t-butylphosphine)palladium(0); sodium t-butanolate / 5,5-dimethyl-1,3-cyclohexadiene / 12 h / Reflux; Inert atmosphere
  • 30
  • [ 1246308-85-9 ]
  • C33H32BBrO [ No CAS ]
  • C51H42BNO2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
66.7% With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In toluene for 24h; Inert atmosphere; Reflux; 7 Synthesis of Compound 50 of Example 7; The synthetic steps of the compound are as follows: A 150 ml four-necked flask was charged with 0.01 mol of E3 under a nitrogen atmosphere.0.011 mol of compound F6, 0.03 mol of sodium t-butoxide, 1 x 10-4 mol of Pd2 (dba) 3,1×10-4 mol of tri-tert-butylphosphine, 50 ml of toluene, and heating under reflux for 24 hours.Sampling the plate, the reaction is complete, naturally cooled, filtered, the filtrate is steamed, passed through the silica gel column,The target product was obtained with a purity of 98.5% and a yield of 66.7%.
  • 31
  • [ 1246308-85-9 ]
  • C33H32BBrO [ No CAS ]
  • C51H42BNO2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
59.7% With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In toluene for 24h; Inert atmosphere; Reflux; 8 A 150 ml four-necked flask was charged with 0.01 mol of E5 under a nitrogen atmosphere.0.011 mol of compound F6, 0.03 mol of sodium t-butoxide, 1 x 10-4 mol of Pd2 (dba) 3,1×10-4 mol of tri-tert-butylphosphine, 50 ml of toluene, and heating under reflux for 24 hours.Sampling the plate, the reaction is complete, naturally cooled, filtered, the filtrate is steamed, passed through the silica gel column,The target product was obtained with a purity of 98.1% and a yield of 59.7%.
  • 32
  • [ 462652-01-3 ]
  • [ 1246308-85-9 ]
  • C31H17BrN2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
66% Stage #1: 12H-benzofuro[3,2-a]carbazole With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.5h; Stage #2: 3’-bromo-5’-fluoro-[1,1‘-biphenyl]-2-carbonitrile In N,N-dimethyl-formamide; mineral oil at 150℃; for 18h; 5 Synthesis of Intermediate (F) 9.02 g (35.06 mmol) of 12H-benzofuro[3,2-a]carbazole was mixed with 100 mL of dimethyl formamide, followed by cooling to a temperature of 0° C. 1.54 g (38.57 mmol) of sodium hydride (60% dispersion in mineral oil) was slowly added thereto, followed by stirring at a temperature of 0° C. for 30 minutes. A solution, in which 10.65 g (38.57 mmol) of 3′-bromo-5′-fluoro-[1,1′-biphenyl]-2-carbonitrile was mixed with 40 mL of dimethyl formamide, was slowly added to the resulting product for 10 minutes. Subsequently, the reaction temperature was raised to a temperature of 150° C., followed by stirring for 18 hours. Once the reaction was complete, the resulting mixture was cooled to room temperature, followed by addition of an ammonium chloride aqueous solution. The organic layer was extracted by using dichloromethane, and the organic extract was dried with magnesium sulfate. Subsequently, the dry organic extract was filtered and concentrated under reduced pressure. The resulting residue was separated and purified by silica gel column chromatography to obtain a desired compound, 11.80 g of Intermediate (F) (at a yield of 66%). LC-Mass (calculated value: 512.05 g/mol, measured value: M+1=513 g/mol)
  • 33
  • [ 462652-01-3 ]
  • [ 1246308-85-9 ]
  • C43H24N2OS [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C 1.2: 18 h / 150 °C 2.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / tetrahydrofuran; water / Reflux
  • 34
  • [ 1246308-85-9 ]
  • C30H18BrNO [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sodium carbonate / toluene; ethanol; water / 1 h / Inert atmosphere 1.2: 15 h / Reflux 2.1: bromine; acetic acid / 5 h / 0 - 20 °C
  • 35
  • [ 2052-07-5 ]
  • [ 1246308-85-9 ]
  • C30H19NO [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 2-Bromobiphenyl; 12H-benzofuro[3,2-a]carbazole With sodium carbonate In ethanol; water; toluene for 1h; Inert atmosphere; Stage #2: With tetrakis(triphenylphosphine) palladium(0) In ethanol; water; toluene for 15h; Reflux; III.3 (3) A 500 mL three-necked flask, under the protection of nitrogen, add 0.05 mol of intermediate P2-1 and 0.075 mol of raw material J1, dissolve with a mixed solvent (180 ml of toluene, 90 ml of ethanol), and then add 0.15 mol of Na2CO3 aqueous solution (2M). Stir for 1 hour under nitrogen, then add 0.0005 mol Pd (PPh3) 4, heat and reflux for 15 hours, sample the plate, and the reaction is complete. Allow to cool, filter, and spin the filtrate through a silica gel column to obtain intermediate P3-1.
  • 36
  • [ 1246308-82-6 ]
  • [ 1246308-83-7 ]
  • [ 1246308-85-9 ]
YieldReaction ConditionsOperation in experiment
1: 45.79% 2: 52.07% With triphenylphosphine In 1,2-dichloro-benzene Reflux; Inert atmosphere;
  • 37
  • [ 1246308-85-9 ]
  • 2-(2-fluorophenyl)-4,6-diphenyl-1,3,5-triazine [ No CAS ]
  • 12-(2-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-12H-benzofuro[3,2-a]carbazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
6.95% Stage #1: 12H-benzofuro[3,2-a]carbazole With caesium carbonate In N,N-dimethyl-formamide for 0.5h; Inert atmosphere; Stage #2: 2-(2-fluorophenyl)-4,6-diphenyl-1,3,5-triazine In N,N-dimethyl-formamide at 130℃; for 18h; Inert atmosphere;
  • 38
  • [ 577-19-5 ]
  • [ 1246308-85-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / tetrahydrofuran; water / 12 h / Reflux; Inert atmosphere 2: triphenylphosphine / 1,2-dichloro-benzene / Reflux; Inert atmosphere
Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / toluene; ethanol; water / Reflux 2: triphenylphosphine / 1,2-dichloro-benzene / 180 °C
  • 39
  • dibenzofuran-2-ylboronic acid [ No CAS ]
  • [ 1246308-85-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / tetrahydrofuran; water / 12 h / Reflux; Inert atmosphere 2: triphenylphosphine / 1,2-dichloro-benzene / Reflux; Inert atmosphere
Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / toluene; ethanol; water / Reflux 2: triphenylphosphine / 1,2-dichloro-benzene / 180 °C
  • 40
  • [ 53846-85-8 ]
  • [ 1246308-85-9 ]
  • 2-(12H-benzofuro[3,2-a]carbazol-12-yl)dibenzo[b,d]thiophene 5,5-dioxide [ No CAS ]
YieldReaction ConditionsOperation in experiment
60% With tri-tert-butyl phosphine; palladium diacetate; sodium t-butanolate In toluene at 110℃; for 18h; Inert atmosphere; 2.5. Synthesis of 2-(12H-benzofuro[3,2-a]carbazol-12-yl)dibenzo[b,d]thiophene 5,5-dioxide (DBT-INFUR) A mixture of 2-bromodibenzothiophene 5,5-dioxide (DBTO-Br, 1.0g, 3.38 mmol), 12H-benzofuro[3,2-a]carbazole (DBF-INFUR, 1.0 g,3.88 mmol), Pd(OAc)2 (0.05 g, 0.20 mmol), 10% t-Bu3P in toluene (0.98ml, 4.06 mmol), NaOtBu (1.0 g, 10.40 mmol) and 80 ml of anhydroustoluene was added in a two-neck round-bottom flask equipped with acondenser. The mixture refluxed at 110 °C for 18 h inert atmospherewhile stirring. The crude residues were separated by a silica column andn-hexane- dichloromethane solvent system to obtain the target moleculeDBT-INFUR of 0.96g.Yield: 60%; Pale yellow solid; 1H NMR (500 MHz, CDCl3) 8.25-8.27 (d, J 8.5 Hz, 1H), 8.18-8.19 (d, J 7.5 Hz, 1H), 8.11-8.13(d, J 8 Hz, 1H), 7.96 (s, 1H), 7.91-7.93 (m, 1H), 7.75-7.77 (d, J 7.5Hz, 1H), 7.55-7.64 (m, 4H), 7.37-7.44 (m, 3H), 7.25-7.31 (m, 1H),6.92-6.95 (t, J 7.5 Hz, 1H), 6.03-6.04 (d, J 8 Hz, 1H)); 13C NMR(500 MHz, CDCl3) 156.7, 155.8, 144.8, 141.4, 138.4, 137.3, 135.4,134.2, 134.0, 131.3, 130.6, 130.5, 126.3, 125.6, 124.5, 124.0, 122.8,122.7, 122.5, 122.1, 121.8, 121.6, 120.0, 119.8, 119.6, 11.4, 109.9,109.0, 105.8. MS (APCI) m/z: 472.28 for C30H17NO3S [(M H)]; MS(TOF) m/z: 471.0929 for C30H17NO3S (471.0929); Anal. Calcd for C30H17NO3S (%): C, 76.42; H, 3.63; N, 2.97; O, 10.18; S, 6.80. Found: C,75.32; H, 3.62; N, 3.05; O, 9.97; S, 6.51.
  • 41
  • [ 947770-80-1 ]
  • [ 1246308-85-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / water / 8 h / 110 °C 2: triethyl phosphite / 24 h / 180 °C / Inert atmosphere
  • 42
  • [ 1246308-85-9 ]
  • C30H17Br [ No CAS ]
  • C48H27NO [ No CAS ]
YieldReaction ConditionsOperation in experiment
79.5% With potassium <i>tert</i>-butylate In toluene at 120℃; for 24h; Inert atmosphere; 1 Example 1 Synthesis of compound 7: Dissolve 0.01 mol of reactant A-1 and 0.012 mol of reactant B-1 in 150 mL of toluene, add 0.015 mol of potassium tert-butoxide, and react at 120°C for 24 hours under a nitrogen atmosphere. Sample the spot plate and wait until the reaction is complete. , Cooling, filtering, rotating the filtrate to remove the solvent, and passing the crude product through a silica gel column to obtain compound 7 with a yield of 79.5percent and a purity of 99.15percent by HPLC;
  • 43
  • [ 50548-45-3 ]
  • [ 1246308-85-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: palladium diacetate; 1,1'-bis-(diphenylphosphino)ferrocene; sodium t-butanolate / toluene / Inert atmosphere; Reflux 2: palladium diacetate; potassium carbonate; tricyclohexylphosphine tetrafluoroborate / N,N-dimethyl acetamide / 12 h / Reflux; Inert atmosphere
  • 44
  • C18H12ClNO [ No CAS ]
  • [ 1246308-85-9 ]
YieldReaction ConditionsOperation in experiment
72% With palladium diacetate; potassium carbonate; tricyclohexylphosphine tetrafluoroborate In N,N-dimethyl acetamide for 12h; Reflux; Inert atmosphere; 4.8 (8) Add Intermediate 4-1 (1.96g, 6.7mmol), palladium acetate (0.30g, 1.3mmol), potassium carbonate (4.62g, 33.5mmol) in a dry 100ml three-necked flask,Tricyclohexylphosphine fluoroborate (1.43g, 3.9mmol), take 20ml of N,N-dimethylacetamide, reflux and stir for 12 hours under nitrogen protection. After the reaction is complete, the solvent is removed by distillation under reduced pressure, extraction, spin-drying, and column chromatography to obtain Intermediate 3-2 with a yield of 72%
  • 45
  • [ 1246308-85-9 ]
  • 2-(2-bromophenyl)-1,3,5-triazine [ No CAS ]
  • 12-(2-(1,3,5-triazin-2-yl)phenyl)-12H-benzofuran[3,2-a]carbazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
20% With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; copper(l) iodide; 18-crown-6 ether; potassium carbonate at 180℃; for 48h; Inert atmosphere; 4.9 (9) Combine 2-(2-bromophenyl)-1,3,5-triazine (0.68g, 2.9mmol), intermediate 3-2 (0.62g, 2.4mmol), cuprous iodide (0.28g , 1.4mmol), K2CO3 (2.04g, 14.7mmol) and 18-crown-6 (0.37g, 1.4mmol) were dissolved in 3mL DMPU solution. Under the protection of nitrogen, heat to 180°C and react for 48h. After the reaction is terminated, cool to room temperature, extract, spin-dry, and column chromatography. The product 33 was obtained by column chromatography with petroleum ether and dichloromethane with a yield of 20%
  • 46
  • [ 95-51-2 ]
  • [ 1246308-85-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: palladium diacetate; 1,1'-bis-(diphenylphosphino)ferrocene; sodium t-butanolate / toluene / Inert atmosphere; Reflux 2: palladium diacetate; potassium carbonate; tricyclohexylphosphine tetrafluoroborate / N,N-dimethyl acetamide / 12 h / Reflux; Inert atmosphere
  • 47
  • [ 1246308-85-9 ]
  • C39H20ClN3O3 [ No CAS ]
  • C57H30N4O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate In o-xylene for 16h; Reflux; 2.b b) 3-Biphenyl-3-yl-9-[9-(4,6-diphenyl-[1,3,5]triazin-2-yl)-dibenzofuran-2-yl]-9H-carbazole General procedure: will 21.4 g(42.7 mmol; 1.00 eq.) of 2-{12-bromo-8-oxatricyclo[7.4.0.02,7] trideca -1(9),2(7),3,5,12-hexaen-3-yl}-4,6-diphenyl-1,3,5-triazine [CAS 1822310-63-3], 13.0 g (40.7 mmol; 1.10 eq.) of 3-biphenyl-3-yl-9H-carbazole [CAS 1643526-99-1] and 7.82 g (81.4 mmol; 2.00 eq.) of sodium tert-butoxide [CAS 865-47-4] suspended in 500 ml o-xylene [CAS 95-47-6]. Add 1.50 g (3.66 mmol; 9 mol%) of dicyclohexyl (2',6'-dimethoxybiphenyl-2-yl)phosphine (SPhos) [CAS 657408-07-6] and 1.12 g (1.22 mmol; 3 mol%) of tris(dibenzylideneacetone)dipalladium [CAS 51364-51-3], The reaction mixture was heated under reflux for 16 h. The reaction mixture was cooled to room temperature and the solvent was removed under reduced pressure. The obtained solid was washed with 300 ml ethanol, Repeated recrystallization with a mixture of heptane and xylene. Hot filtration through Alox, followed by sublimation under high vacuum, to obtain a purified product, As a colorless solid, 21.1 g (29.5 mmol; 69%).
  • 48
  • [ 1246308-85-9 ]
  • 2-{12-chloro-8-oxatricyclo[7.4.0.02,7]trideca-1(13),2(7),3,5,9,11-hexen-3-yl}-4-{8-oxatricyclo[7.4.0.02,7]trideca-1(9),2,4,6,10,12-hexen-3-yl}-6-phenyl-1,3,5-triazine [ No CAS ]
  • C51H28N4O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate In o-xylene for 16h; Reflux; 2.b b) 3-Biphenyl-3-yl-9-[9-(4,6-diphenyl-[1,3,5]triazin-2-yl)-dibenzofuran-2-yl]-9H-carbazole General procedure: will 21.4 g(42.7 mmol; 1.00 eq.) of 2-{12-bromo-8-oxatricyclo[7.4.0.02,7] trideca -1(9),2(7),3,5,12-hexaen-3-yl}-4,6-diphenyl-1,3,5-triazine [CAS 1822310-63-3], 13.0 g (40.7 mmol; 1.10 eq.) of 3-biphenyl-3-yl-9H-carbazole [CAS 1643526-99-1] and 7.82 g (81.4 mmol; 2.00 eq.) of sodium tert-butoxide [CAS 865-47-4] suspended in 500 ml o-xylene [CAS 95-47-6]. Add 1.50 g (3.66 mmol; 9 mol%) of dicyclohexyl (2',6'-dimethoxybiphenyl-2-yl)phosphine (SPhos) [CAS 657408-07-6] and 1.12 g (1.22 mmol; 3 mol%) of tris(dibenzylideneacetone)dipalladium [CAS 51364-51-3], The reaction mixture was heated under reflux for 16 h. The reaction mixture was cooled to room temperature and the solvent was removed under reduced pressure. The obtained solid was washed with 300 ml ethanol, Repeated recrystallization with a mixture of heptane and xylene. Hot filtration through Alox, followed by sublimation under high vacuum, to obtain a purified product, As a colorless solid, 21.1 g (29.5 mmol; 69%).
  • 49
  • [ 1246308-85-9 ]
  • 5-(4,6-diphenyl-1,3,5-triazin-2-yl)-3,4-difluoro-2-phenylbenzonitrile [ No CAS ]
  • 5-(4,6-diphenyl-1,3,5-triazin-2-yl)-3,4-bis(benzofuro[3,2-a]carbazole-12-yl)-2-phenylbenzonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
50% With potassium carbonate In N,N-dimethyl-formamide at 165℃; for 12h; 2 Synthesis of 5-(4,6-diphenyl-1,3,5-triazin-2-yl)-3,4-bis(benzofuro[3,2-a]carbazole-12- yl)-2-phenylbenzonitrile (Compound 1753) The mixture of the 5-(4,6-diphenyl-1,3,5-triazin-2-yl)-3,4-difluoro-2-phenylbenzonitrile 16a (50 mg, 0.11 mmol), K2CO3 (46 mg, 0.34 mmol) and 12H-Benzofuro[3,2-a]carbazole (86 mg, 0.37 mmol) were added and stirred at 165 for 12h. Water and MeOH was added to reaction mixture and the propitiated solid was filtrated and washed by water and MeOH. The residue was purified by column chromatography (toluene/hexane=4/1) and recrystallized by CHCl3 and hexane to obtain 5-(4,6-diphenyl-1,3,5-triazin-2-yl)-3,4-bis(benzofuro[3,2-a]carbazole- 12-yl)-2-phenylbenzonitrile 1753 (52 mg, 0.06 mmol, 50%). 1H-NMR (400 MHz, CDCl3, d): 9.57 (s, 1H), 8.67 (d, J = 8.0 Hz, 1H), 7.99 (d, J = 8.0 Hz, 4H), 7.73-7.54 (m, 5H), 7.49-7.33 (m, 7H), 7.18-7.11 (m, 4H), 7.09-7.23 (m, 4H), 6.99-6.85 (m, 4H), 6.72-7.65 (m, 3H), 6.52 (t, J = 8.0 Hz, 2H), 6.35 (d, J = 8.0 Hz, 1H). MS (ASAP): 921.50 (M+H+). Calcd for C64H36N6O2, 920.29.
  • 50
  • [ 1246308-85-9 ]
  • C14H8BrFOS [ No CAS ]
  • C32H18BrNO2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% With caesium carbonate In N,N-dimethyl-formamide at 120℃; for 6h; Inert atmosphere;
  • 51
  • [ 1246308-85-9 ]
  • C18H10INO2S [ No CAS ]
  • C36H20N2O3S [ No CAS ]
YieldReaction ConditionsOperation in experiment
With copper(l) iodide; potassium carbonate; N,N`-dimethylethylenediamine In 5,5-dimethyl-1,3-cyclohexadiene for 15h; Inert atmosphere; Reflux; 6 Step 2: Preparation of compound PP281 General procedure: 24.0mmol Intermediate Int-1 is dissolved inIn 80mL of xylene,Under the protection of nitrogen,Add 20.0mmol of 3,6-di-tert-butylcarbazole (CAS: 37500-95-1),80.0mmol of anhydrous potassium carbonate,2.0mmol of cuprous iodide and5.0mmol of N,N’-dimethylethylenediamine,The temperature was raised and refluxed and stirred for 15 hours,Cooled to room temperature, filtered, the filtrate was concentrated to dryness under reduced pressure, and separated and purified with a silica gel column to obtain the product PP281, a white solid, with a yield of 92%.
  • 52
  • [ 1246308-85-9 ]
  • 1-bromo-2-chloro-4-iodobenzene [ No CAS ]
  • C24H13BrClNO [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tris-(dibenzylideneacetone)dipalladium(0); potassium <i>tert</i>-butylate; triphenylphosphine In toluene for 12h; Inert atmosphere; Reflux; A-2 In a three-necked flask, add 0.012mol of raw material A-2 under an atmosphere of nitrogen. 0.01mol of raw material B-2, 0.03mol of potassium tert-butoxide, 1×10-4mol of Pd2(dba)3, 1×10-4mol of triphenylphosphine, 150ml of toluene, heating and refluxing for 12 hours, Sampling point plate, showing that there is no raw material B-2 remaining; natural cooling, filtration, rotary evaporation of the filtrate, and silica gel column to obtain intermediate F-2.
  • 53
  • [ 1246308-85-9 ]
  • C60H40N2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: potassium <i>tert</i>-butylate; tris-(dibenzylideneacetone)dipalladium(0); triphenylphosphine / toluene / 12 h / Inert atmosphere; Reflux 2: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / toluene; water / 24 h / 105 °C / Inert atmosphere 3: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / toluene; water / 24 h / 105 °C / Inert atmosphere
  • 54
  • [ 1246308-85-9 ]
  • C30H18ClNO [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium <i>tert</i>-butylate; tris-(dibenzylideneacetone)dipalladium(0); triphenylphosphine / toluene / 12 h / Inert atmosphere; Reflux 2: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / toluene; water / 24 h / 105 °C / Inert atmosphere
  • 55
  • [ 1246308-85-9 ]
  • C20H11BrO [ No CAS ]
  • C38H21NO2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
62.8% With 1,10-Phenanthroline; potassium carbonate In toluene at 110℃; for 8h; Inert atmosphere; Synthesis of compound 34: Fill a 500ml three-necked flask with nitrogen, add 10g intermediate 1, 8.2g compound 34-1, 6.0g potassium carbonate, 0.52g 1,10-phenanthroline, 200ml toluene, stir until the raw materials are completely dissolved, then add 0.41 g cuprous iodide, The reaction was heated to 110°C and stirred for 8 hours. The reaction was stopped after the complete consumption of Intermediate 1 as monitored by TLC. The reaction solution was cooled to room temperature and washed with water to neutrality. The organic phase was dried with anhydrous sodium sulfate and purified by a silica gel column. The eluent was concentrated and recrystallized 9.5 g of compound 34 was obtained, with a yield of 62.8%.
  • 56
  • [ 1246308-85-9 ]
  • 6-(9H-carbazol-9-yl)-12-(4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-12H-benzofuro[3,2-a]carbazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: N-Bromosuccinimide / N,N-dimethyl-formamide / 8 h / 20 °C 2: potassium <i>tert</i>-butylate; XPhos; tris-(dibenzylideneacetone)dipalladium(0) / o-xylene / 6 h / Reflux 3: potassium <i>tert</i>-butylate; tri-tert-butyl phosphine; palladium diacetate / 1,4-dioxane; water; toluene / 6 h / Reflux
  • 57
  • [ 1246308-85-9 ]
  • [ 23449-08-3 ]
  • C39H24N4O [ No CAS ]
YieldReaction ConditionsOperation in experiment
68.3% With tri-tert-butyl phosphine; potassium <i>tert</i>-butylate; palladium diacetate In 1,4-dioxane; water; toluene for 6h; Reflux;
  • 58
  • [ 1246308-85-9 ]
  • 6,6'-(4-fluoro-1,3-phenylene)bis(2,4-diphenyl-1,3,5-triazine) [ No CAS ]
  • C54H33N7O [ No CAS ]
YieldReaction ConditionsOperation in experiment
33% Stage #1: 12H-benzofuro[3,2-a]carbazole; 6,6'-(4-fluoro-1,3-phenylene)bis(2,4-diphenyl-1,3,5-triazine) In N,N-dimethyl-formamide Inert atmosphere; Reflux; Stage #2: With caesium carbonate In N,N-dimethyl-formamide for 4h; Inert atmosphere; 1.2 Step 2) Synthesis of Compound 1 Compound 1-a (20 g, 35.8 mmol) and 12H-benzofuro[3,2-a]carbazole (10.1 g, 39.4 mmol) were added to 400 ml of DMF under a nitrogen atmosphere, and the mixture was stirred under reflux. Then, cesium carbonate (35 g, 107.4 mmol) was added thereto and stirred. After reacting for 4 hours, the reaction mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and then the organic layer was distilled. This was dissolved in chloroform, and washed twice with water. The organic layer was then separated, anhydrous magnesium sulfate was added, stirred, and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography and then subjected to sublimation purification to give 9.4 g of Compound 1. (yield: 33%, MS: [M+H]+=797)
  • 59
  • [ 1246308-85-9 ]
  • C42H22N4O [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: Cs2CO3 / dimethyl sulfoxide / 15 h / 100 °C / Inert atmosphere 2: Cs2CO3; palladium diacetate; tricyclohexylphosphine tetrafluorohydroborate / N,N-dimethyl acetamide / 16 h / 140 °C / Inert atmosphere 3: triphenylphosphine / 1,2-dichloro-benzene / 36 h / 175 °C / Inert atmosphere 4: bis(tri-tertiary-butylphosphine)palladium(0); sodium tertiary butoxide / 5,5-dimethyl-1,3-cyclohexadiene / 5 h / 140 °C
  • 60
  • [ 1246308-85-9 ]
  • C24H12N2O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: Cs2CO3 / dimethyl sulfoxide / 15 h / 100 °C / Inert atmosphere 2: Cs2CO3; palladium diacetate; tricyclohexylphosphine tetrafluorohydroborate / N,N-dimethyl acetamide / 16 h / 140 °C / Inert atmosphere
Multi-step reaction with 2 steps 1.1: Cs2CO3 / dimethyl sulfoxide / 20 h / 100 °C / Inert atmosphere 2.1: Cs2CO3 / N,N-dimethyl acetamide / 0.5 h / 140 °C / Inert atmosphere 2.2: 16 h / 80 - 140 °C
Multi-step reaction with 2 steps 1: Cs2CO3 / dimethyl sulfoxide / 20 h / 100 °C / Inert atmosphere 2: Cs2CO3; palladium diacetate; tricyclohexylphosphine tetrafluoroborate / 16 h / 80 - 140 °C / Inert atmosphere
  • 61
  • [ 1246308-85-9 ]
  • C24H12N2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: Cs2CO3 / dimethyl sulfoxide / 15 h / 100 °C / Inert atmosphere 2: Cs2CO3; palladium diacetate; tricyclohexylphosphine tetrafluorohydroborate / N,N-dimethyl acetamide / 16 h / 140 °C / Inert atmosphere 3: triphenylphosphine / 1,2-dichloro-benzene / 36 h / 175 °C / Inert atmosphere
Multi-step reaction with 3 steps 1.1: Cs2CO3 / dimethyl sulfoxide / 20 h / 100 °C / Inert atmosphere 2.1: Cs2CO3 / N,N-dimethyl acetamide / 0.5 h / 140 °C / Inert atmosphere 2.2: 16 h / 80 - 140 °C 3.1: triphenylphosphine / 1,2-dichloro-benzene / 36 h / 175 °C / Inert atmosphere
Multi-step reaction with 3 steps 1: Cs2CO3 / dimethyl sulfoxide / 20 h / 100 °C / Inert atmosphere 2: Cs2CO3; palladium diacetate; tricyclohexylphosphine tetrafluoroborate / 16 h / 80 - 140 °C / Inert atmosphere 3: triphenylphosphine / 1,2-dichloro-benzene / 36 h / 175 °C / Inert atmosphere
  • 62
  • [ 1246308-85-9 ]
  • [ 21397-07-9 ]
  • C24H13ClN2O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
59% With Cs2CO3 In dimethyl sulfoxide at 100℃; for 15h; Inert atmosphere; Synthesis of intermediate a1-1: Combine 12H-benzofuro[3,2-a]carbazole (32.5 g; 126.2 mmol), 2-chloro-3-fluoronitrobenzene (22.2 g; 126.2 mmol), cesium carbonate (25.4 g; 126.2 mmol) and dry DMSO (300 mL) were added to a nitrogen-protected round-bottomed flask, and the temperature was raised to 100 °C under stirring for 15 h; the reaction mixture was cooled to room temperature, the mixture was extracted with dichloromethane, the organic phase was collected, and anhydrous After drying the organic phase over magnesium sulfate, the solvent was removed under reduced pressure to obtain a crude product; the crude product was purified by silica gel column chromatography using dichloromethane/n-heptane as eluent to obtain a white solid intermediate a1-1 (30.7 g; 59% )
59% With Cs2CO3 In dimethyl sulfoxide at 100℃; for 20h; Inert atmosphere; Synthesis of intermediate a1-1: Combine 12H-benzofuro[3,2-a]carbazole (32.5 g; 126.2 mmol), 2-chloro-3-fluoronitrobenzene (22.2; 126.2 mmol), cesium carbonate (25.4 g; 126.2 mmol) and dry DMSO (300 mL) was added to a nitrogen-protected round-bottomed flask, and the temperature was raised to 100°C under stirring for 20 h; the reaction mixture was cooled to room temperature, the mixture was extracted with toluene, the organic phase was collected, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure; the crude product was purified by silica gel column chromatography using toluene/n-heptane as eluent to give intermediate a1-1 (30.7 g; 59%)
59% With Cs2CO3 In dimethyl sulfoxide at 100℃; for 20h; Inert atmosphere; Synthesis of intermediate a1-1: Combine 12H-benzofuro[3,2-a]carbazole (32.5 g; 126.2 mmol), 2-chloro-3-fluoronitrobenzene (22.2; 126.2 mmol), cesium carbonate (25.4 g; 126.2 mmol) and Dry DMSO (300 mL) was added to a nitrogen-protected round-bottomed flask, and the temperature was raised to 100 °C under stirring for 20 h; The reaction mixture was cooled to room temperature, the mixture was extracted with toluene, the organic phase was collected, dried over anhydrous magnesium sulfate, and then the solvent was removed under reduced pressure; the crude product was purified by silica gel column chromatography using toluene/n-heptane as the eluent to obtain an intermediate Body a1-1 (30.7 g; 59%)
  • 63
  • [ 1246308-85-9 ]
  • 2,3,5-trifluoro-4,6-diphenylbenzonitrile [ No CAS ]
  • C37H20F2N2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
35% Stage #1: 12H-benzofuro[3,2-a]carbazole With sodium hydride In N,N-dimethyl-formamide at 20℃; for 1h; Inert atmosphere; Stage #2: 2,3,5-trifluoro-4,6-diphenylbenzonitrile In N,N-dimethyl-formamide at 0℃; for 10h; Inert atmosphere; 1-2 (1-2) Synthesis of Intermediate 2 Dimethylformamide (40 mL) was added to 0.35 g (14.7 mmol) of sodium hydride and 1.26 g (4.90 mmol) of 12H- [3,2-a] -benzoflocarbazole under a nitrogen stream, and the mixture was added at room temperature for 1 hour. Stirred.The reaction mixture was added to a solution of Intermediate 1 (2.17 g, 7.00 mmol) in dimethylformamide (20 mL) at 0 ° C. and stirred for 10 hours.Then, the temperature was raised to 10 ° C., and the mixture was stirred for 6 hours.Water was added to the reaction solution for quenching, extraction was performed with ethyl acetate, the organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and the solvent was distilled off.The crude product was purified by silica gel column chromatography (hexane: toluene = 2: 1) to obtain 0.93 g (1.70 mmol, yield 35%) of Intermediate 2 as a pale yellow solid.
  • 64
  • [ 1246308-85-9 ]
  • C30H15BrN2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: Cs2CO3 / dimethyl sulfoxide / 20 h / 100 °C / Inert atmosphere 2.1: Cs2CO3 / N,N-dimethyl acetamide / 0.5 h / 140 °C / Inert atmosphere 2.2: 16 h / 80 - 140 °C 3.1: triphenylphosphine / 1,2-dichloro-benzene / 36 h / 175 °C / Inert atmosphere 4.1: tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium tertiary butoxide / 5,5-dimethyl-1,3-cyclohexadiene / 16 h / 135 °C / Inert atmosphere
  • 65
  • [ 1246308-85-9 ]
  • C42H25N3O [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: Cs2CO3 / dimethyl sulfoxide / 20 h / 100 °C / Inert atmosphere 2.1: Cs2CO3 / N,N-dimethyl acetamide / 0.5 h / 140 °C / Inert atmosphere 2.2: 16 h / 80 - 140 °C 3.1: triphenylphosphine / 1,2-dichloro-benzene / 36 h / 175 °C / Inert atmosphere 4.1: tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium tertiary butoxide / 5,5-dimethyl-1,3-cyclohexadiene / 16 h / 135 °C / Inert atmosphere 5.1: tris-(dibenzylideneacetone)dipalladium(0); sodium tertiary butoxide; dicyclohexyl({2’,6’-dimethoxy-[1,1‘-biphenyl]-2-yl})phosphane / toluene / 8 h / Reflux
  • 66
  • [ 1246308-85-9 ]
  • C30H16N2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: Cs2CO3 / dimethyl sulfoxide / 20 h / 100 °C / Inert atmosphere 2: Cs2CO3; palladium diacetate; tricyclohexylphosphine tetrafluoroborate / 16 h / 80 - 140 °C / Inert atmosphere 3: triphenylphosphine / 1,2-dichloro-benzene / 36 h / 175 °C / Inert atmosphere 4: tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium tertiary butoxide / 5,5-dimethyl-1,3-cyclohexadiene / 16 h / 135 - 140 °C / Inert atmosphere
  • 67
  • [ 1246308-85-9 ]
  • C66H43N3OS [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: NBS / 4 h / 20 °C 2: tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium tertiary butoxide / toluene / 8 h / 110 °C 3: palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; anhydrous potassium acetate / N,N-dimethyl-formamide / 8 h / 110 °C 4: tetrakis-(triphenylphosphine)-palladium; sodium hydroxide / tetrahydrofuran; lithium hydroxide monohydrate / 4 h / 70 °C 5: tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium tertiary butoxide / toluene / 8 h / 110 °C 6: tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium tertiary butoxide / toluene / 3 h / 110 °C
  • 68
  • [ 1246308-85-9 ]
  • C66H45N3O [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: NBS / 4 h / 20 °C 2: tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium tertiary butoxide / toluene / 8 h / 110 °C 3: palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; anhydrous potassium acetate / N,N-dimethyl-formamide / 8 h / 110 °C 4: tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium tertiary butoxide / toluene / 8 h / 110 °C 5: tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium tertiary butoxide / toluene / 3 h / 110 °C
  • 69
  • [ 1246308-85-9 ]
  • C66H43N3OS [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: NBS / 4 h / 20 °C 2: tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium tertiary butoxide / toluene / 8 h / 110 °C 3: palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; anhydrous potassium acetate / N,N-dimethyl-formamide / 8 h / 110 °C 4: tetrakis-(triphenylphosphine)-palladium; sodium hydroxide / tetrahydrofuran; lithium hydroxide monohydrate / 4 h / 70 °C 5: tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium tertiary butoxide / toluene / 8 h / 110 °C 6: tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium tertiary butoxide / toluene / 3 h / 110 °C
  • 70
  • [ 1246308-85-9 ]
  • C30H17BrClNO [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: NBS / 4 h / 20 °C 2: tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium tertiary butoxide / toluene / 8 h / 110 °C 3: palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; anhydrous potassium acetate / N,N-dimethyl-formamide / 8 h / 110 °C 4: tetrakis-(triphenylphosphine)-palladium; sodium hydroxide / tetrahydrofuran; lithium hydroxide monohydrate / 4 h / 70 °C
  • 71
  • [ 1246308-85-9 ]
  • C42H27ClN2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: NBS / 4 h / 20 °C 2: tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium tertiary butoxide / toluene / 8 h / 110 °C 3: palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; anhydrous potassium acetate / N,N-dimethyl-formamide / 8 h / 110 °C 4: tetrakis-(triphenylphosphine)-palladium; sodium hydroxide / tetrahydrofuran; lithium hydroxide monohydrate / 4 h / 70 °C 5: tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium tertiary butoxide / toluene / 8 h / 110 °C
  • 72
  • [ 1246308-85-9 ]
  • C48H31ClN2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: NBS / 4 h / 20 °C 2: tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium tertiary butoxide / toluene / 8 h / 110 °C 3: palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; anhydrous potassium acetate / N,N-dimethyl-formamide / 8 h / 110 °C 4: tetrakis-(triphenylphosphine)-palladium; sodium hydroxide / tetrahydrofuran; lithium hydroxide monohydrate / 4 h / 70 °C 5: tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium tertiary butoxide / toluene / 8 h / 110 °C
  • 73
  • [ 1246308-85-9 ]
  • C48H26(2)H5ClN2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: NBS / 4 h / 20 °C 2: tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium tertiary butoxide / toluene / 8 h / 110 °C 3: palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; anhydrous potassium acetate / N,N-dimethyl-formamide / 8 h / 110 °C 4: tetrakis-(triphenylphosphine)-palladium; sodium hydroxide / tetrahydrofuran; lithium hydroxide monohydrate / 4 h / 70 °C 5: tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium tertiary butoxide / toluene / 8 h / 110 °C
  • 74
  • [ 1246308-85-9 ]
  • C36H22BrNO [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: NBS / 4 h / 20 °C 2: tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium tertiary butoxide / toluene / 8 h / 110 °C
  • 75
  • [ 1246308-85-9 ]
  • C42H25BrClNO [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: NBS / 4 h / 20 °C 2: tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium tertiary butoxide / toluene / 8 h / 110 °C 3: palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; anhydrous potassium acetate / N,N-dimethyl-formamide / 8 h / 110 °C
  • 76
  • [ 1246308-85-9 ]
  • C54H35ClN2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: NBS / 4 h / 20 °C 2: tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium tertiary butoxide / toluene / 8 h / 110 °C 3: palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; anhydrous potassium acetate / N,N-dimethyl-formamide / 8 h / 110 °C 4: tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium tertiary butoxide / toluene / 8 h / 110 °C
  • 77
  • [ 1246308-85-9 ]
  • C36H21BrClNO [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: NBS / 4 h / 20 °C 2: tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium tertiary butoxide / toluene / 8 h / 110 °C 3: palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; anhydrous potassium acetate / N,N-dimethyl-formamide / 8 h / 110 °C 4: tetrakis-(triphenylphosphine)-palladium; sodium hydroxide / tetrahydrofuran; lithium hydroxide monohydrate / 4 h / 70 °C
  • 78
  • [ 1246308-85-9 ]
  • C54H35ClN2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: NBS / 4 h / 20 °C 2: tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium tertiary butoxide / toluene / 8 h / 110 °C 3: palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; anhydrous potassium acetate / N,N-dimethyl-formamide / 8 h / 110 °C 4: tetrakis-(triphenylphosphine)-palladium; sodium hydroxide / tetrahydrofuran; lithium hydroxide monohydrate / 4 h / 70 °C 5: tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium tertiary butoxide / toluene / 8 h / 110 °C
  • 79
  • [ 1246308-85-9 ]
  • [ 1606981-69-4 ]
  • [ 2724261-19-0 ]
YieldReaction ConditionsOperation in experiment
87.55 % With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; sodium t-butanolate In o-xylene at 180℃; 3 [Synthesis Example 3] Synthesis of Compound B-73 Compound B-73-1 (20 g, 0.078 mol), compound B-73-2 (43.3 g, 0.093 mol), Pd2(dba)2 (3.6 g, 0.0039 mol), S-Phos (3.2 g, 0.0078 mol), NaOt-Bu (18.7 g, 0.194 mol), and 520 mL of o-xylene were added into a flask, and then stirred under reflux at 180° C. for 3 hours. The mixture was cooled to room temperature, and then methanol was added thereto followed by filtering the solid under reduced pressure. The obtained solid was dissolved in chloroform, and then separated by column chromatography to obtain compound B-73 (43.6 g, yield: 87.55%).
Same Skeleton Products
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