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Product Details of [ 1338919-70-2 ]

CAS No. :1338919-70-2 MDL No. :MFCD32670210
Formula : C18H11NO Boiling Point : -
Linear Structure Formula :- InChI Key :DZINJFQFEBORIC-UHFFFAOYSA-N
M.W : 257.29 Pubchem ID :57997537
Synonyms :

Safety of [ 1338919-70-2 ]

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

Application In Synthesis of [ 1338919-70-2 ]

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

  • Downstream synthetic route of [ 1338919-70-2 ]

[ 1338919-70-2 ] Synthesis Path-Downstream   1~82

  • 1
  • [ 3616-56-6 ]
  • [ 78842-63-4 ]
  • [ 1338919-70-2 ]
YieldReaction ConditionsOperation in experiment
39% With acetic acid;Reflux; Synthesis example B2: Synthesis of 12H-benzofuranyl[2,3-a]carbazole (compound 2); Compound 1 (2.0 g, 1 eq.) is added to acetic acid (90 ml) and heated to reflux. (Dimethylamino)acetaldehyde diethyl acetal (95percent; 14.6 g, 10 eq.) is added dropwise in portions to the solution. The reaction is stirred at reflux until no reactant is present any longer. 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 CH2CI2/n-hex) gives the product 2 (0.85 g, 39percent yield).1H NMR (CD2CI2, 400 MHz): "5 = 8.68 (br s, 1 H), 8.15 (d, 1 H), 8.06 (dd, 2H), 7.83 (d, 1 H), 7.67 (d, 1 H), 7.59 (d, 1 H), 7.47 (dd, 2H), 7.41 (dd, 1 H), 7.30 (dd, 1 H).
39% With acetic acid; sodium chloride; In dichloromethane; water; Synthesis Example B2Synthesis of 12H-benzofuranyl[2,3-a]carbazole (compound 2)Compound 1 (2.0 g, 1 eq.) is added to acetic acid (90 ml) and heated to reflux. (Dimethylamino)acetaldehyde diethyl acetal (95percent; 14.6 g, 10 eq.) is added dropwise in portions to the solution.The reaction is stirred at reflux until no reactant is present any longer.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 CH2Cl2/n-hex) gives the product 2 (0.85 g, 39percent yield).1H NMR (CD2Cl2, 400 MHz): delta=8.68 (br s, 1H), 8.15 (d, 1H), 8.06 (dd, 2H), 7.83 (d, 1H), 7.67 (d, 1H), 7.59 (d, 1H), 7.47 (dd, 2H), 7.41 (dd, 1H), 7.30 (dd, 1H).
  • 2
  • [ 100-63-0 ]
  • [ 1338919-70-2 ]
  • 3
  • [ 626-00-6 ]
  • [ 1338919-70-2 ]
  • [ 1338919-71-3 ]
YieldReaction ConditionsOperation in experiment
68% With potassium carbonate;copper; In Tridecane; at 185℃; for 72h; Synthesis example B3: Synthesis of 1, 3-bis(12-(12H-benzofuranyl[2, 3- a])carbazolyl)benzene (compound 3); (3); The suspension of compound 2 (1.95 g, 7.6 mmol), 1 ,3-diiodobenzene (98%; 1.28 g, 3.8 mmol), potassium carbonate (2.63 g, 19 mmol) and copper powder (0.19 g, 3 mmol) in n-tridecane (5 ml) is heated to 185C and stirred for 72 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. After double recrystallization in CH2CI2/n- hexane (15% CH2CI2), 1 .3 g of product were obtained. Yield: 68%. 1H NMR (CD2CI2, 400 MHz): «5 = 8.20 (d, 2H), 8.14 (d, 2H), 8.04-8.06 (m, 3H), 7.92- 7.93 (m, 3H), 7.89 (d, 2H), 7.80 (d, 2H) 7.46-7.32 (m, 10H).
  • 4
  • [ 29786-93-4 ]
  • [ 76-86-8 ]
  • [ 1338919-70-2 ]
  • [ 1338919-63-3 ]
YieldReaction ConditionsOperation in experiment
36.7% In methanol; diethyl ether; hexane; Synthesis Example A3 Synthesis of 11,12-diphenyl-3,8-bis(triphenylsilyl)-11H,12H-indolo[2,3-a]carbazole (compound 3) n-Butyllithium (1.6 M in hexane, 4.6 ml, 2.1 eq.) is slowly added dropwise at room temperature under nitrogen to a suspension of compound 2 (2.0 g, 1 eq.) in ultradry diethyl ether (55 ml) and the mixture is stirred at room temperature for a further 2 h. A solution of chlorotriphenylsilane (97%; 3.22 g, 3 eq.) in ultradry diethyl ether (20 ml) is slowly added dropwise to the reaction. The reaction is stirred at reflux overnight. After 22 h, the experiment is cooled to room temperature and 20 ml of methanol is added. The reaction is transferred to a separating funnel with methylene chloride and washed with distilled water (3*50 ml). Organic phase dried with sodium sulfate, concentrated and dried at 65 C. under reduced pressure. LC (S102, 3:7 CH2Cl2/cyclohexane) gives 1.12 g of compound 3 (36.7% yield). 1H NMR (CD2Cl2, 400 MHz): δ=8.37 (s, 2H), 7.97 (s, 2H), 7.63 (d, 12H), 7.36-7.50 (m, 20H), 7.29 (d, 2H), 7.08-7.14 (m, 6H) 6.78 (d, 4H).
  • 5
  • [ 132-64-9 ]
  • [ 1338919-70-2 ]
  • 6
  • [ 65344-26-5 ]
  • [ 1338919-70-2 ]
  • 7
  • C18H12BrNO [ No CAS ]
  • [ 1338919-70-2 ]
YieldReaction ConditionsOperation in experiment
46% With tetrakis(triphenylphosphine) palladium(0); potassium acetate; In N,N-dimethyl-formamide; for 12.0h;Reflux; 16 g (35 mmol) of , 0.8 g (0.7 mmol) of tetrakis (triphenylphosphine) palladium, 4.1 g (42 mmol) of potassium acetate and 200 mL of dimethylformaldehyde were charged into a 500 mL reactor And the mixture was stirred at reflux for 12 hours. After cooling to room temperature, the reaction product is poured into excess H2O and the precipitated solid is filtered. The solid was separated by column chromatography to obtain 6 g. (Yield: 46%)
44% With tetrakis(triphenylphosphine) palladium(0); palladium diacetate; In N,N-dimethyl-formamide; at 110℃; for 12.0h; Inthe above [Reaction formula 2] the compound from 60 g (201 mmol) isdisplayed, Tetrakis (triphenylphosphine) palladium (0) 0.7 g (4 mmol), thepotassium acetate 24.3 g (213 mmol) and 600 ml of dimethyl formamide wasstirred in the reactor for 12 hours at 110 . After the completion of the reaction, it iscooled at room temperature and then extracted. The organic layer was filtered under reduced pressure by chromatographicseparation to obtain 20 g of a compound represented by the . (Yield44%)
  • 8
  • [ 1338919-70-2 ]
  • C24H14BrNO [ No CAS ]
  • 9
  • [ 1338919-70-2 ]
  • C30H26BNO3 [ No CAS ]
  • 10
  • [ 1338919-70-2 ]
  • C32H20BrNO3 [ No CAS ]
  • 11
  • [ 1338919-70-2 ]
  • C33H24BrNO2 [ No CAS ]
  • 12
  • [ 1338919-70-2 ]
  • C33H22BrNO [ No CAS ]
  • 13
  • [ 1338919-70-2 ]
  • C63H44N2O [ No CAS ]
  • 14
  • [ 1338919-70-2 ]
  • C18H10BrNO [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% With N-Bromosuccinimide; In N,N-dimethyl-formamide; for 4.0h; Inthe above [Reaction formula 3] displayed as was dissolved in 150 mlof dimethylformamide obtained from compound 20 g (78 mmol), then Dimethylformamide50 ml and N- bromosuccinimide 13.8 g (78 mmol) was dissolved and then slowlyadded dropwise to the reactor, and the mixture was stirred for 4 hours. Whenthe reaction is completed distilled water was added dropwise at roomtemperature to form brown crystals and the crystals were filtered and separatedby chromatographic separation to obtain 17g of the compound represented by the. (Yield 65%)
58% With N-Bromosuccinimide; In dichloromethane; at -10℃; In a 3L flask,87.0 g (0.34 mol) of intermediate 7 are mixed with 3.0 L of dichloromethane,The internal temperature of the flask was lowered to -10C.Keep the internal temperature at -10C,At the same time, 66.2 g (0.37 mol) of N-bromosuccinimide was slowly added thereto.When the reaction is complete,After removing the solvent from it,The product is processed by column chromatography.Intermediate 8 was obtained (66.0 g, 58% yield).
  • 15
  • [ 1338919-70-2 ]
  • C24H22BNO3 [ No CAS ]
  • 16
  • [ 1338919-70-2 ]
  • C26H17NO3 [ No CAS ]
  • 17
  • [ 1338919-70-2 ]
  • C27H21NO2 [ No CAS ]
  • 18
  • [ 1338919-70-2 ]
  • C27H19NO [ No CAS ]
  • 19
  • [ 591-50-4 ]
  • [ 1338919-70-2 ]
  • C24H15NO [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% With tricalcium diphosphate; copper(l) iodide; rac-diaminocyclohexane; In 1,4-dioxane; for 12.0h;Reflux; Inthe above [Reaction formula 3] is obtained from compound 20 g (78mmol), Iodine benzene 23.8 g (117 mmol), 1,2-cyclohexane-diamine 26.6 g (233mmol), Cooper iodide 0.7 g (4 mmol), tricalcium phosphate 49.4 g (233 mmol) and 200mL of 1,4-dioxane was refluxed for 12 hours. When the reaction is completed itwas filtered under reduced pressure in a hot state. It is separated by chromatographicseparation to obtain 21g of the compound represented by the . (Yield81%)
  • 21
  • [ 577-19-5 ]
  • [ 1338919-70-2 ]
  • C24H14N2O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
82% With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate; In toluene; for 18.0h;Reflux; The compound prepared in Step 2 (20 g, 77.73 mmol)Was dissolved in toluene, and then 1-bromo-2-nitrobenzene,Pd(dba)3 (2.14 g, 2.33 mmol), P(t-Bu)3 (1.11 ml, 4.66 mmol), NaO(tbu) (14.94 g, 155.47 mmol)Was added at room temperature and refluxed with stirring for 18 hours. After completion of the reaction, water and ethyl acetate were added. The separated organic layer was dried over anhydrous magnesium sulfate and silica gel filter, and the solvent was concentrated under reduced pressure. The resulting mixture was recrystallized from dichloromethane and acetone to obtain 24.12 g of the title compound (D) ).
  • 23
  • C18H12ClNO [ No CAS ]
  • [ 1338919-70-2 ]
YieldReaction ConditionsOperation in experiment
88% With palladium diacetate; potassium carbonate; tri tert-butylphosphoniumtetrafluoroborate; at 90℃; Sub 4-c-1 (45.2 g, 154 mmol) was added to DMA (mL) followed by Pd(OAc)2 (1.04 g, 4.61 mmol),K2CO3 (63.8 g, 461 mmol), P(t-Bu)3H.BF4 (g, 9.23 mmol) was added and stirred at 90 C.After the reaction is completed, the mixture is extracted with CH2Cl2 and water, and the organic layer is dried over MgSO4 and concentrated.Thereafter, the produced compound was recrystallized after applying a silica gel column to obtain 34.8 g (yield: 88%) of the product.
87% With palladium diacetate; caesium carbonate; tricyclohexylphosphine tetrafluoroborate; In N,N-dimethyl acetamide; for 12.0h;Reflux; Inert atmosphere; In a 3L flask,114.2 g (0.39 mol) of Intermediate 6, 8.7 g (38.9 mmol) of palladium acetate,379.9 g (1.2 mol) of cesium carbonate and 28.6 g (77.73 mol)Tricyclohexylphosphine-tetrafluoroborate is mixed with 1.3 L of N,N-dimethylacetamide,The mixture was heated and refluxed under a stream of nitrogen for 12 hours.When the reaction is over,After volatilizing and removing the solvent from it,Add 2L of methanol to it,And the crystallized solid is filteredDissolved in dichlorobenzene,Filtered on silica gel/celite,After removing the right amount of organic solvents,Recrystallized from methanol,Intermediate 7 was obtained (87.0 g, yield 87%).
With tri-tert-butyl phosphine; palladium 10% on activated carbon; 1,3-bis-(diphenylphosphino)propane; potassium carbonate; In N,N-dimethyl-formamide; for 24.0h;Reflux; The compound (B) (31 g, 105.53 mmol) prepared in the above step 1 was dissolved inAfter dissolving in N, N-dimethylformamide (280 ml), 10% Pd-C (7.11 g, 31.66 mmol)Bis (diphenylphosphino) propane, 1,3-bis (diphenylphosphino) 13.058 g, 31.66 mmol),T-tributylphosphine(52.07 ml, 105.53 mmol),K2CO3 (29.17 g, 211.06 mmol), and the mixture was refluxed and stirred for 24 hours.After completion of the reaction, water and ethyl acetate were added. The separated organic layer was dried over an silica gel filter and anhydrous magnesium sulfate, and the solvent was concentrated under reduced pressure. The resulting mixture was recrystallized from dichloromethane and hexaneTo obtain the title compound (C) (20.64 g, 76%).
55.32 g With palladium diacetate; caesium carbonate; tricyclohexylphosphine tetrafluoroborate; In N,N-dimethyl acetamide; at 170℃;Inert atmosphere; Add compound 1-c (theoretical 95.1g, 0.324mol) in a 2L three-necked flask, tricyclohexylphosphinium tetrafluoroborate (11.9g, 0.1eq), cesium carbonate (211g, 2eq)And DMAc (1000ml), under N2 protection,Add palladium acetate (3.63g, 0.05eq),The temperature was raised to 170C and the reaction was stirred for 5-24 hours. HPLC monitored compound 1-c≤0.5%. The reaction was stopped, DMAc was evaporated under reduced pressure until almost no droplets dripped out, 1000ml of water was added, cooled and stirred overnight for crystallization, suction filtered, the filter cake was added with 150g of 100-200 mesh silica gel for sand production, and 1kg of 100-200 mesh silica gel was packed into the column. Column chromatography, PE/DCM=20/110/15/13/12/1, collect product spots, concentrate under reduced pressure to dryness, to obtain compound 1-d: 55.32g.

  • 24
  • [ 1338919-70-2 ]
  • C24H14N2O [ No CAS ]
  • 25
  • [ 1338919-70-2 ]
  • (4,6-diphenyl-1,3,5-triazin-2-yl)-16H-benzofuro[3',2':6,7]indolo[3,2,1-de]phenazine [ No CAS ]
  • 26
  • [ 1338919-70-2 ]
  • 3-(dibenzo[b,d]furan-2-yl)-2-fluorobenzonitrile [ No CAS ]
  • C37H20N2O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
17% Compound 450 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 (5) was used instead of carbazole and the reaction temperature was changed to 150 C (yield 17%).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).
  • 27
  • [ 1338919-70-2 ]
  • [ 19542-05-3 ]
  • C50H28N4O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
73.5% With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate; In toluene; for 24.0h;Inert atmosphere; Reflux; In the 250ml three-necked bottle,Under nitrogen protection,0.01 mol of 2,5-bis (4-bromophenyl) -1,3,4-oxadiazole was added,0.024 mol of intermediate B1,0.04 mol of sodium tert-butoxide,1 x 10-4 mol Pd (dba) 3,1 x 10-4 mol of tri-tert-butylphosphine,150 ml of toluene,Heated to reflux for 24 hours,Sampling point plate,The reaction is complete;Natural cooling,filter,The filtrate is steamed,Column chromatography to obtain the target product,HPLC purity 99.2%Yield 73.5%;
  • 28
  • [ 1338919-70-2 ]
  • 2-(4'-bromobiphenyl-3-yl)-10,10-dioxo-10H-thioxanthene-9-one [ No CAS ]
  • C43H25NO4S [ No CAS ]
YieldReaction ConditionsOperation in experiment
63% With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate; In toluene; for 24.0h;Reflux; Inert atmosphere; 250 ml three-neck bottle, in an atmosphere of nitrogen, adding 0.01 µM 2 - (4' - bromo biphenyl -3 - yl) - 10, 10 - dioxa - 10H - saisai anthracene -9 - ketone, 0.015 µM compound M8, 0.03mol tert sodium butylate, 1 × 10-4Mol Pd2(Dba)3, 1 × 10-4Mol tri-butyl phosphate, 150 ml toluene, heating reflux for 24 hours, the sampling board, natural cooling, filtration, filtrate and steaming and, over silica gel column, to obtain the target product, purity 99.80%, yield 63%.
  • 29
  • [ 1338919-70-2 ]
  • C30H26BNO3 [ No CAS ]
  • 30
  • [ 1338919-70-2 ]
  • C43H25N3O [ No CAS ]
  • 31
  • [ 589-87-7 ]
  • [ 1338919-70-2 ]
  • C24H14BrNO [ No CAS ]
YieldReaction ConditionsOperation in experiment
55% With copper(l) iodide; 1,10-Phenanthroline; potassium carbonate; In N,N-dimethyl-formamide; for 24.0h;Reflux; Synthesis of Intermediate (B) (0242) 10.0 g (38.9 mmol) of <strong>[1338919-70-2]12H-benzofuro[2,3-a]carbazole</strong>, 13.2 g (46.6 mmol) of 1-bromo-4-iodobenzene, 1.48 g (7.77 mmol) of copper iodide (CuI), 16.1 g (117 mmol) of potassium carbonate (K2CO3), and 2.80 g (15.6 mmol) of 1,10-phenanthroline were dissolved in 130 mL of DMF, and the mixed solution was stirred under reflux for 24 hours. After the completion of the reaction, the reaction solution was cooled to room temperature and filtered by passing through a silica gel column under reduced pressure, and the filtrate was concentrated under reduced pressure. The resulting product obtained therefrom was separated by silica gel column chromatography, thereby obtaining 8.81 g (yield: 55%) of the desired compound, Intermediate (B). (0243) LC-Mass (calculated: 411.03 g/mol, found: M+1=412 g/mol).
  • 32
  • [ 1338919-70-2 ]
  • 3-bromo-1,5-bis(4-dibenzofuran-yl)benzene [ No CAS ]
  • C48H27NO3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
71.8% With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate; In toluene; for 24.0h;Reflux; 250 ml of a three-necked flask, 0.01 mol of intermediate A2, 0.015 mol of raw material B1, 0.03 mol of sodium tert-butoxide, 1 × 10-4mol of Pd2(Dba)3, 1 × 10-4mol tri-tert-butyl phosphine, 150ml toluene, heated and refluxed for 24 hours, the sampling plate, the reaction is complete; natural cooling, filtration, the filtrate steamed, silica gel column, the target product, purity 98.9% yield of 71.8%.
  • 33
  • [ 1338919-70-2 ]
  • C30H19BrO [ No CAS ]
  • C48H29NO2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
72.3% With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate; In toluene; for 24.0h;Reflux; 250 ml of a three-necked flask, 0.01 mol of the intermediate A1, 0.015 mol of the raw material B1, 0.03 mol of sodium tert-butoxide, 1 × 10-4mol of Pd2(Dba)3, 1 × 10-4mol tri-tert-butyl phosphine, 150ml toluene, heated and refluxed for 24 hours, the sampling plate, the reaction is complete; natural cooling, filtration, the filtrate steamed, silica gel column, the target product, purity 98.8% Rate of 72.3%.
  • 34
  • 10-phenylanthracene-9-boronic acid [ No CAS ]
  • [ 1338919-70-2 ]
  • C44H27NO [ No CAS ]
YieldReaction ConditionsOperation in experiment
62% With tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate; tri tert-butylphosphoniumtetrafluoroborate; In 5,5-dimethyl-1,3-cyclohexadiene; for 4.0h;Reflux; To a 300 mL reactor was added 4 g (11 mmol)4.2 g (13 mmol) of , 0.2 g (0.22 mmol) of tris (dibenzylideneacetone) dipalladium,0.3 g (1.1 mmol) of tri-tert-butylphosphonium tetrafluoroborate,2.1 g (22 mmol) of sodium tertiary butoxide and 70 mL of xylene are added, and the mixture is refluxed with stirring for 4 hours. After filtration at high temperature, the filtrate is concentrated under reduced pressure.And recrystallized from methylene chloride and acetone to obtain 4.5 g of the compound of the formula (2). (Yield: 62%).
  • 35
  • [ 1338919-70-2 ]
  • C30H18ClNO [ No CAS ]
  • 36
  • [ 1338919-70-2 ]
  • C30H17NO [ No CAS ]
  • 37
  • [ 577-19-5 ]
  • 2,2-dimethyl-5-phenyl-4H-benzo[d][1,3]dioxin-4-one [ No CAS ]
  • [ 1338919-70-2 ]
  • 38
  • [ 1195665-78-1 ]
  • [ 1338919-70-2 ]
YieldReaction ConditionsOperation in experiment
71.5% With triphenylphosphine; In 1,2-dichloro-benzene; at 180℃; for 12.0h;Inert atmosphere; 2) In a 250 ml three-neck flask, under the protection of nitrogen, add 0.04 mol of intermediate 1-1,Mix 0.04 mol of triphenylphosphine and 100 ml of o-dichlorobenzene, stir and heat to 180C for 12 hours, sample the point plate, and show that there is no intermediate 1-1 remaining.The reaction was complete; the filtrate was filtered, and the filtrate was distilled under reduced pressure until no fraction was detected. A neutral silica gel column was used to obtain Intermediate 1-2, HPLC purity 99.2%, yield 71.5%;
70.5% With triphenylphosphine; In 1,2-dichloro-benzene; at 180℃; for 12.0h;Inert atmosphere; 2)In a 250ml three-vial bottle,Under nitrogen protection,Add 0.04 mole of intermediate 1-1,0.04 mol of triphenylphosphine,100ml o-dichlorobenzene,Heat to 180C,Stir the reaction for 12 hours,Sampling point board,Shows that there is no remaining 3-(2-nitrophenyl)dibenzo[b,d]furan,Complete reaction;filter,The filtrate was evaporated under reduced pressure until no fractions were obtained.Over neutral silica gel column,Obtain intermediate B1,HPLC purity 99.2%,Yield 70.5%;
With tri-tert-butyl phosphine; In toluene; at 120℃; for 24.0h;Inert atmosphere; In a 500mL three-neck bottle,Under the protection of nitrogen,0.2 mol of compound M2-1 and 500 mL of toluene were added,Stir and dissolve,Add 0.25molTri-tert-butylphosphine,Stir and heat to 120 C,Reflow reaction for 24 hours,Sampling plate,Show no raw materials remaining,Complete reaction;Cool naturally to room temperature,filter,The filtrate is layered,The organic phase is decanted and steamed to a fraction without distillation.Neutral silicon rubber column,Obtaining compound M2-2;
With triphenylphosphine; In 1,2-dichloro-benzene;Inert atmosphere; In a 250mL three-necked flask, under the protection of nitrogen,Add 0.02mol intermediate 3-o-nitrobenzodibenzofuran and dissolve it with 100mL o-dichlorobenzene,Add 0.03mol of triphenylphosphine, stir and react at 170190 for 1216h,After the reaction, it was cooled to room temperature, filtered, and the filtrate was evaporated under reduced pressure and passed through a neutral silica gel column to obtain intermediate (1-2);

  • 39
  • 2,2-dimethyl-5-phenyl-4H-benzo[d][1,3]dioxin-4-one [ No CAS ]
  • [ 1338919-70-2 ]
  • 40
  • [ 577-19-5 ]
  • [ 1338919-70-2 ]
  • 41
  • [ 1338919-70-2 ]
  • C55H31NO2 [ No CAS ]
  • 42
  • [ 1338919-70-2 ]
  • [ 1338919-74-6 ]
YieldReaction ConditionsOperation in experiment
68.9% With bromine; acetic acid; at 0 - 20℃; for 12.0h; 3) In a 250 ml three-necked flask, add 0.04 mol of Intermediate 1-2,100 ml of acetic acid was stirred and dissolved, cooled to 0 C. in an ice salt bath, and 0.05 mol of Br2 dissolved in 50 ml of acetic acid was weighed. The bromine acetic acid solution was slowly added dropwise to the above reaction system. After the dropwise addition was completed, the temperature was raised to room temperature and the reaction was stirred. 12 Hours; sampling point plate, showing no intermediate 1-2 remaining, complete reaction; add NaOHAqueous solution was neutralized, extracted with dichloromethane, layered, and the organic phase was filtered.The filtrate was evaporated under reduced pressure until no fractions were obtained.After neutral silica gel column, intermediate 1-3 was obtained, HPLC purity 99.3%, yield 68.9%;
With bromine; acetic acid; at 0 - 20℃; for 12.0h;Inert atmosphere; In a 250mL three-neck bottle,Under the protection of nitrogen,Add 0.1 mol of compound M2-2,Add 100 mL of acetic acid,Stir and dissolve at room temperature,At 0 C,Slowly add 50 mL of 0.12 mol of Br2 acetic acid solution.Stir at room temperature for 12 hours.Neutralize to neutral with NaOH aqueous solution (2mol/L),Solid precipitation,Filter the filter cake,Drying under vacuum,Over neutral silica gel column,Obtaining compound M2-3;
  • 43
  • [ 1338919-70-2 ]
  • C30H17NO2 [ No CAS ]
  • 44
  • [ 1338919-70-2 ]
  • 2-(4-bromophenyl)-4,6-diphenylpyrimidine [ No CAS ]
  • C40H25N3O [ No CAS ]
YieldReaction ConditionsOperation in experiment
63.4% With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate; In toluene; for 24.0h;Inert atmosphere; Reflux; 250ml four-necked flask, under a nitrogen atmosphere,Add 0.01 mol of raw material A1, 0.025 mol of raw material B1,0.04 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 1 was obtained with a purity of 98.1%.Yield 63.4%.
  • 45
  • [ 1338919-70-2 ]
  • 2-(4'-bromobiphenyl-4-yl)-4,6-diphenylpyrimidine [ No CAS ]
  • C46H29N3O [ No CAS ]
YieldReaction ConditionsOperation in experiment
63.8% With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate; In toluene; for 24.0h;Inert atmosphere; Reflux; 250ml four-necked flask, under a nitrogen atmosphere,Add 0.01 mol of raw material A2, 0.025 mol of raw material B1,0.04mol of sodium tert-butoxide,2 × 10-4 mol Pd2 (dba) 3, 2 × 10-4 mol tri-tert-butylphosphine, 150 ml toluene, heated to reflux for 24 hours, sampling point plate,The reaction is complete; naturally cooled, filtered, the filtrate vortexed,The silica gel column gives the target product 3,98.3% purity, yield 63.8%.
  • 46
  • [ 1338919-70-2 ]
  • C24H16BrNO [ No CAS ]
  • C42H26N2O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
76.4% With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate; In toluene; at 105℃; for 24.0h;Inert atmosphere; 2) In a 250ml three-neck bottle,Under the protection of nitrogen,Add 0.01 mol of intermediate A1,0.012 mol of raw material F1,150 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).Obtaining the target product, HPLC purity 99.3%, yield 76.4%;
  • 47
  • [ 1338919-70-2 ]
  • C27H22BrN [ No CAS ]
  • C45H32N2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
76.2% With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate; In toluene; at 105℃; for 24.0h;Inert atmosphere; In a 250ml three-neck bottle,Under the protection of nitrogen,Add 0.01 mol of intermediate C1,0.012 mol of raw material F1,150 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 subjected to vacuum distillation (-0.09 MPa, 85 C), and passed through a neutral silica gel column.The target product was obtained, the HPLC purity was 98.7%, and the yield was 76.2%;
  • 48
  • [ 1338919-70-2 ]
  • 2-bromo-9,9,10-triphenyl-9,10-dihydroacridine [ No CAS ]
  • C49H32N2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
74.8% With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate; In toluene; at 105℃; for 24.0h;Inert atmosphere; In a 250ml three-neck bottle,Under the protection of nitrogen,Add 0.01 mol of intermediate D1,0.012 mol of raw material F1,150 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).Obtaining the target product, HPLC purity 98.9%, yield 74.8%;
  • 49
  • [ 1338919-70-2 ]
  • C30H20N2O [ No CAS ]
  • 50
  • [ 1338919-70-2 ]
  • C36H38BBr [ No CAS ]
  • C54H48BNO [ No CAS ]
YieldReaction ConditionsOperation in experiment
70.5% With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate; In toluene; for 24.0h;Inert atmosphere; Reflux; A 150 ml four-necked flask was charged with 0.01 mol of E1 under a nitrogen atmosphere.0.011 mol of compound F1, 0.03 mol of sodium tert-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 98.3% and a yield of 70.5%.
  • 51
  • [ 1338919-70-2 ]
  • C40H40BBr [ No CAS ]
  • C58H50BNO [ No CAS ]
YieldReaction ConditionsOperation in experiment
61.8% With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate; In toluene; for 24.0h;Inert atmosphere; Reflux; A 150 ml four-necked flask was charged with 0.01 mol of E2 under a nitrogen atmosphere.0.011 mol of compound F2, 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 61.8%.
  • 52
  • [ 1338919-70-2 ]
  • C23H13BrN2 [ No CAS ]
  • C41H23N3O [ No CAS ]
YieldReaction ConditionsOperation in experiment
76.3% With tris-(dibenzylideneacetone)dipalladium(0); potassium tert-butylate; In toluene; at 110℃; for 24.0h;Inert atmosphere; In a 500 mL three-necked flask, 0.03 mol was added under nitrogen protection.Raw material A-1,0.03 mol of raw material B-1, 250 mL of toluene was stirred and mixed.Then add 0.09molPotassium tert-butoxide, 0.0015molPd2(dba)3, heated to 110 C,Reflow reaction for 24 hours;Cool naturally to room temperature, filter,The filtrate was subjected to vacuum distillation (-0.09 MPa, 85 C).Over neutral silica gel column, Obtaining Compound 1, HPLC purity 99.3%, yield 76.3%
  • 53
  • [ 1073-06-9 ]
  • [ 1338919-70-2 ]
  • C24H14FNO [ No CAS ]
YieldReaction ConditionsOperation in experiment
73% With tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate; In o-xylene; for 24.0h;Reflux; 13.18 g (51.23 mmol) of <strong>[1338919-70-2]12H-benzofuro[2,3-a]carbazole</strong>, 11.65 g (66.60 mmol) of 1-bromo-3-fluorobenzene, 2.95 g (5.12 mmol) of bis(dibenzylideneacetone)palladium(0), 9.85 g (102.46 mmol) of sodium tert-butoxide, and 4.15 g (10.25 mmol) of tri-tert-butylphosphine solution (50%) were dissolved in 130 mL of O-xylene and stirred for 24 hours under reflux. After the reaction was completed, the reaction product was cooled to room temperature and filtered under reduced pressure through silica gel. The filtrate was concentrated under reduced pressure. The product obtained therefrom was separated by silica gel column chromatography to obtain 13.21 g (yield of 73%) of Intermediate (F). (0288) LC-Mass (Calcd: 351.11 g/mol, Found: M+1=352 g/mol)
  • 54
  • [ 1338919-70-2 ]
  • C50H31N5O [ No CAS ]
  • 55
  • [ 1338919-70-2 ]
  • [ 1256544-16-7 ]
  • C36H19NO3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
72.4% With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate; In toluene; at 105℃; for 24.0h;Inert atmosphere; In a 250ml three-necked bottle, under the protection of nitrogen, add 0.01mol intermediate B1, 0.012mol raw material A1,150ml toluene was stirred and mixed, then 5 × 10-5molPd2 (dba) 3 was added,5 × 10-5mol P (t-Bu) 3, 0.03mol sodium tert-butoxide, heated to 105 , refluxed for 24 hours,Sampling point plate, showing no bromine remaining, the reaction is complete; naturally cooled to room temperature,After filtration, the filtrate was spin-evaporated to no fraction and passed through a neutral silica gel column to obtain the target product. The HPLC p
  • 56
  • [ 1338919-70-2 ]
  • C18H9BrO2 [ No CAS ]
  • C36H19NO3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
76.5% With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate; In toluene;Inert atmosphere; Under a nitrogen atmosphere, add 0.01 mol of intermediate D-1, 0.015 mol of raw material F-1, 0.03 mol of sodium tert-butoxide, 5 × 10-5 mol of Pd2 (dba) 3 and 5 × 10-5 mol to a 500 ml three-necked flask Tert-butyl phosphorus, then add 150ml of toluene to dissolve it, heat to 100 C, reflux for 24 hours, observe the reaction by TLC until the reaction is complete. Naturally cool to room temperature, filter, and spin the filtrate to no fraction. The resulting material was purified through a silica gel column (petroleum ether as eluent) to obtain the target product with a purity of 99.6% and a yield of 76.5%.
  • 57
  • [ 29874-83-7 ]
  • [ 1338919-70-2 ]
  • C32H19N3O [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate; In toluene; at 100℃; Sub 4-1 (34.8 g, 135 mmol), Toluene (500 mL),Sub 5-1 (32.6 g, 135 mmol), Pd2(dba)3 (3.72 g, 4.06 mmol),P(t-Bu)3 (1.64 g, 8.12 mmol),NaOt-Bu (26.0 g, 271 mmol) was added and stirred at 100 C.After the reaction was completed, extracted with CH2Cl2 and water, the organic layer was dried over MgSO4, concentrated, and the resulting compound was silicagel column and recrystallized to obtain 48.7 g of product (yield: 78%).
  • 58
  • [ 1338919-70-2 ]
  • C37H25Br [ No CAS ]
  • C55H35NO [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tris-(dibenzylideneacetone)dipalladium(0); potassium tert-butylate; triphenylphosphine; In toluene; for 12.0h;Inert atmosphere; Reflux; Further, under an atmosphere of nitrogen,0.01mol of raw material C-1, 0.012mol of intermediate 1, 0.03mol of potassium tert-butoxide, 1×10-4mol of Pd2(dba)3, 1×10-4mol of triphenylphosphine,150ml toluene was added to 250ml three-necked bottle,Heat to reflux for 12 hours, sample the spot, the reaction is complete;Natural cooling, filtering, filtrate rotary evaporation, passing through silica gel column,Compound 1 is obtained;
  • 59
  • [ 591-18-4 ]
  • [ 1338919-70-2 ]
  • C24H14BrNO [ No CAS ]
YieldReaction ConditionsOperation in experiment
With copper(l) iodide; potassium carbonate; rac-diaminocyclohexane; In 5,5-dimethyl-1,3-cyclohexadiene;Reflux; <strong>[1338919-70-2]12H-benzofuro[2,3-a]carbazole</strong> 25.7g (100mmol)Mix with 30g (100mmol) of m-bromoiodobenzene and dissolve in xylene,Add CuI (10mmol), 1,2-cyclohexanediamine (10mmol),Potassium carbonate (300mmol), heated to reflux, the reaction solution was added with water and extracted.The organic layer was concentrated and subjected to silica gel column chromatography to obtain Intermediate M6-2.
YieldReaction ConditionsOperation in experiment
With triphenylphosphine; In 1,2-dichloro-benzene; at 220℃; for 16.0h; General procedure: Sub 1-I-16 (58.30 g, 184.86 mmol) obtained in the above synthesis was added to a round bottom flask, triphenylphosphine (121.22 g, 462.15 mmol) was added, and 1,100 mL of 1,2-dichlorobenzene was added to 220C. Stir for 16 hours in a melted state. When the reaction is complete, the reaction product is concentrated under reduced pressure and then quenched with water, and the solid reaction product is obtained by filtering, and the reaction product that has come out of the filtrate is obtained by removing water, filtration under reduced pressure, drying with MgSO4, and concentration. The resulting compound was subjected to a silicagel column. Among the two isomers, the lower spot on TLC (Methylene chloride: hexane=1: 3) was separated and recrystallized to obtain 22.00 g (yield: 42%) of the product.
  • 61
  • [ 1338919-70-2 ]
  • 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[2,3-a]carbazole-12-yl)-2-phenylbenzonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
69% With potassium carbonate; In N,N-dimethyl-formamide; at 150℃; for 12.0h; The mixture of the 5-(4,6-diphenyl-1,3,5-triazin-2-yl)-3,4-difluoro-2-phenylbenzonitrile 17a (50 mg, 0.11 mmol), K2CO3 (46 mg, 0.34 mmol) and 12H-Benzofuro[2,3-a]carbazole (86 mg, 0.37 mmol) were added and stirred at 150 C 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[2,3-a]carbazole- 12-yl)-2-phenylbenzonitrile 1754 (72 mg, 0.08 mmol, 69%). 1H-NMR (400 MHz, CDCl3, d): 9.40 (s, 0.5H), 9.21 (s, 0.5H), 7.95 (d, J = 8.0Hz, 0.5H), 7.84-7.80 (m, 2.5H), 7.78-7.56 (m, 3H), 7.70 (t, J = 8.4Hz, 1H), 7.64-7.50 (m, 6H), 7.48-7.44 (m, 2H), 7.42-7.35 (m, 3H), 7.34-7.28 (m, 1H), 7.25-7.23 (m, 1H), 7.21-7.14 (m, 5H), 7.12- 7.00 (m, 5H), 6.97-6.83 (m, 1H), 6.82-6.69 (m, 3H), 6.48 (t, J = 8.4, 1H). MS (ASAP): 921.39 (M+H+). Calcd for C64H36N6O2, 920.29.
  • 62
  • [ 1338919-70-2 ]
  • [ 773-90-0 ]
  • C28H17NO2 [ No CAS ]
  • 63
  • [ 57638-63-8 ]
  • [ 60656-87-3 ]
  • [ 1338919-70-2 ]
  • 64
  • [ 1338919-70-2 ]
  • C36H12(2)H10BrClN2O [ No CAS ]
  • 65
  • [ 1338919-70-2 ]
  • C48H22(2)H10ClN3O [ No CAS ]
  • 66
  • [ 1338919-70-2 ]
  • C48H21(2)H9BN3O [ No CAS ]
  • 67
  • [ 179897-90-6 ]
  • [ 1338919-70-2 ]
  • C24H12Br2ClNO [ No CAS ]
YieldReaction ConditionsOperation in experiment
93% With caesium carbonate; In N,N-dimethyl-formamide; at 130℃;Inert atmosphere; Add <strong>[1338919-70-2]12H-benzofuro[2,3-a]carbazole</strong> (25.7g, 100mmol) to a 1L single-mouth flask at room temperature,1,3-Dibromo-2-chloro-5-fluorobenzene (34.3g, 120mmol),Cesium carbonate (39.1g, 150mmol), N,N-dimethylformamide (300ml), replaced with nitrogen three times, heated at 130C for reaction overnight. After the reaction stopped, after cooling to room temperature, 500ml of water was added and stirred for 10 minutes, a large amount of white solid was precipitated out, filtered with suction, and the filter cake was boiled and washed with ethanol for 2h.The temperature was lowered and suction filtered to obtain 48.6 g of a white solid product with a yield of 93%.
  • 68
  • [ 1338919-70-2 ]
  • [ 201138-91-2 ]
  • C30H16BrNO2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
61% With bis(tri-t-butylphosphine)palladium(0); sodium t-butanolate; In toluene; for 11.0h;Inert atmosphere; Reflux; In a nitrogen atmosphere, 4,6-dibromodibenzo[b,d]furan (15.0 g, 46.0 mmol) and <strong>[1338919-70-2]12H-benzofuro[2,3-a]carbazole</strong> (13.0 g, 50.6 mmol) were added to 300 mL of toluene, stirred and refluxed. Then, sodium tert-butoxide (NaOtBu, 6.6 g, 69.0 mmol) and bis(tri-tert-butylphosphine)palladium(0) (Pd(P-tBu3)2, 0.7 g, 1.4 mmol) were added. After the reaction for 11 hours, it was cooled to room temperature, the organic layer was separated using chloroform and water, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 14.1 g of compound 9-1. (Yield 61%, MS: [M+H]+= 503)
  • 69
  • [ 1338919-70-2 ]
  • C36H28BNO4 [ No CAS ]
  • 70
  • [ 1338919-70-2 ]
  • C46H24BN3O4 [ No CAS ]
  • 71
  • [ 1338919-70-2 ]
  • 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 15.0h;Inert atmosphere; Reflux; 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%.
  • 72
  • [ 1700-02-3 ]
  • [ 1338919-70-2 ]
  • C27H15ClN4O [ No CAS ]
YieldReaction ConditionsOperation in experiment
64.8% With sodium t-butanolate; In tetrahydrofuran; at 0℃; Add compound 1-d (29.32g, 0.114mol),Compound 1-e (51.5g, 2eq) and ultra-dry THF (400ml), cooled to below 0,Sodium tert-butoxide (16.4g, 1.5eq) was added in batches, and the reaction was stirred at low temperature for 16-24h. Stop the reaction, add 200ml water, stir for 10min,After suction filtration, the filter cake was slurried with 300 ml of toluene at reflux, the temperature was lowered to 40C, and the filter cake was filtered with suction, and the filter cake was dried by air blowing at 85C to obtain compound 1-f (33g, 64.8%).
  • 73
  • [ 1338919-70-2 ]
  • C30H18N2O [ No CAS ]
  • 74
  • [ 1338919-70-2 ]
  • C45H27N5O [ No CAS ]
  • 75
  • [ 1338919-70-2 ]
  • C51H31N5O [ No CAS ]
  • 76
  • [ 1338919-70-2 ]
  • C57H35N5O [ No CAS ]
  • 77
  • [ 1338919-70-2 ]
  • C24H14INO [ No CAS ]
  • 78
  • [ 1338919-70-2 ]
  • C30H19ClN2O [ No CAS ]
  • 79
  • [ 108-86-1 ]
  • [ 1338919-70-2 ]
  • C24H15NO [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium tertiary butoxide; In toluene; for 12.0h;Reflux; Inert atmosphere; <strong>[1338919-70-2]12H-benzofuro[2,3-a]carbazole</strong> (20 g, 77.73 mmol), bromobenzene (30.5 g, 194.33 mmol), NaOtBu (11.21 g, 116.6 mmol), and Pd2(dba)3 (3.56 g, 3.89 mmol) were added to 130 ml of toluene and suspended therein, and P(t-Bu)3 (4.72 ml, 11.66 mmol) were added thereto and then, stirred under reflux for 12 hours under a nitrogen atmosphere. Subsequently, distilled water was added to the reaction solution, and a solid produced therein was filtered and separated under a reduced pressure. The solid was recrystallized with toluene to obtain intermediate M-1 (29.8 g, Yield: 80%).
80% With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium tertiary butoxide; In toluene; for 12.0h;Reflux; Inert atmosphere; <strong>[1338919-70-2]12H-benzofuro[2,3-a]carbazole</strong> (20 g, 77.73 mmol), bromobenzene (30.5 g, 194.33 mmol), NaOtBu (11.21 g, 116.6 mmol), and Pd2(dba)3 (3.56 g, 3.89 mmol) were added to 130 ml of toluene and suspended therein, and P(t-Bu)3 (4.72 ml, 11.66 mmol) was added thereto and then, stirred under reflux for 12 hours under a nitrogen atmosphere. Subsequently, distilled water was added to the reaction solution, and a solid produced in an organic layer due to the distilled water was filtered and separated under a reduced pressure. The solid was dissolved in toluene and then, cooled down to ambient temperature and recrystallized, obtaining Intermediate M-1 (29.8 g, Yield: 80%).LC-MS M+H: 334.12 g/mol
  • 80
  • [ 1338919-70-2 ]
  • C24H16BNO3 [ No CAS ]
  • 81
  • [ 1338919-70-2 ]
  • C45H28N4O [ No CAS ]
  • 82
  • [ 1338919-70-2 ]
  • 2-([1,1‘-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine [ No CAS ]
  • C39H24N4O [ No CAS ]
YieldReaction ConditionsOperation in experiment
85.5% With sodium hydride; In N,N-dimethyl-formamide; at 20℃; for 4.0h; 10 g (37.31 mmol) of Intermediate M-5, 14.75 g (42.91 mmol) of Intermediate M-3, and 2.09 g (52.24 mmol) of sodium hydride were added to 149 ml of DMF and dissolved therein and then, stirred for 4 hours at ambient temperature. When a reaction was completed, a solid produced by adding water thereto was filtered and separated under a reduced pressure and then, dissolved in 100 ml of a 1,2-dichlorobenzene solvent and made to pass silica to obtain a target compound in a liquid state, and 50 ml of n-hexane was added thereto and then, stirred for 4 hours. Subsequently, Compound G-1 (18 g, Yield: 85.5%) was obtained by performing recrystallization in the above method.
Same Skeleton Products
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