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CAS No. : | 1984-49-2 | MDL No. : | MFCD11046470 |
Formula : | C24H16N2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | PUMOFXXLEABBTC-UHFFFAOYSA-N |
M.W : | 332.40 | Pubchem ID : | 12462601 |
Synonyms : |
|
Num. heavy atoms : | 26 |
Num. arom. heavy atoms : | 26 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 0.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 110.6 |
TPSA : | 31.58 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | Yes |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -3.73 cm/s |
Log Po/w (iLOGP) : | 2.68 |
Log Po/w (XLOGP3) : | 6.48 |
Log Po/w (WLOGP) : | 6.62 |
Log Po/w (MLOGP) : | 4.75 |
Log Po/w (SILICOS-IT) : | 6.63 |
Consensus Log Po/w : | 5.43 |
Lipinski : | 1.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 1.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -6.66 |
Solubility : | 0.0000732 mg/ml ; 0.00000022 mol/l |
Class : | Poorly soluble |
Log S (Ali) : | -6.94 |
Solubility : | 0.0000383 mg/ml ; 0.000000115 mol/l |
Class : | Poorly soluble |
Log S (SILICOS-IT) : | -10.01 |
Solubility : | 0.0000000326 mg/ml ; 0.0000000001 mol/l |
Class : | Insoluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.03 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280 | UN#: | N/A |
Hazard Statements: | H302-H317 | Packing Group: | N/A |
GHS Pictogram: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With iron(III) chloride In chloroform at 20℃; for 0.5 h; | Carbazole (10 g, 59.8 mmol), iron (III) chloride (38.8 g, 239.3 mmol) and chloroform (200 mL) were sequentially added to a 400 mL four-necked flask and stirred at room temperature for 30 minutes.After completion of the reaction, the organic solvent was removed under reduced pressure, and the solid obtained was washed by adding methanol.The solid was collected by filtration, and then the same methanol washing was repeated twice to obtain Intermediate 3 (16.7 g, yield 84percent). |
62% | With iron(III) chloride In chloroform at 20℃; | Bicarbazole (BCz) was prepared by chemical oxidation of 9H-carbazole in the presence of FeCl3. To a solution of 9H-carbazole (8.35 g, 100 mmol) in chloroform (150 ml) Iron chloride (anhydrous FeCl 3, 20 g, 120 mmol) was added thereto and stirred at room temperature for 30 minutes. The chloroform was removed from the reaction mixture and concentrated.After filtration with an excess amount of water, BCz (5.5 g, 62percent) was obtained through column chromatography (hexane: ethyl acetate = 2: 1 to 1: 1). |
22% | Stage #1: With iron(III) chloride In chloroform at 20℃; for 0.5 h; Inert atmosphere Stage #2: With acetic acid; zinc In methanol; chloroform; ethyl acetate at 50℃; Inert atmosphere |
Carbazole (12.0 g, 72.0 mmol) and anhydrous FeCl3 (47.0 g, 288 mmol) were dissolved in 240 mLof chloroform and stirred for 30 min under nitrogen. The solution was subsequently poured into alarger quantity of methyl alcohol. The precipitated green powder and zinc powder (18.7 g, 288 mmol)were dissolved in a solution of acetic acid and ethyl acetate (180 mL, 1:1) under nitrogen. The mixturewas heated at 50 °C overnight. The reaction mixture was filtered and washed with hot ethyl acetate.The filtered solution was poured into water and extracted with ethyl acetate. The organics werecombined, washed with brine, and dried with sodium sulfate. After solvent removal, 5.94 g of a brownpowder was obtained. This crude product was purified via vacuum sublimation. Obtained as a whilesolid was 2.53 g (8.0 mmol, 22percent) of BCz. 1H-NMR (400 MHz, DMSO-d6): δ (ppm) 11.28 (s, 2H), 8.51(s, 2H), 8.25 (d, J = 7.7 Hz, 2H), 7.81 (dd, J = 8.4 Hz, J = 1.4 Hz, 2H), 7.58 (d, J = 8.4 Hz, 2H), 7.51 (d,J = 8.1 Hz, 2H), 7.41 (t, J = 7.6 Hz, 2H), 7.19 (t, J = 7.4 Hz, 2H). 13C-NMR (100 MHz, DMSO-d6): δ (ppm)140.7, 139.2, 132.8, 126.1, 125.4, 123.6, 123.2, 120.9, 119.0, 118.6, 111.7, 111.5. |
11% | With iron(III) chloride In methanol at 20℃; for 22 h; | In a 300 mL eggplant flask, 20 g of iron chlorideAnd 5 g of carbazole, and the mixture was vigorously stirred.After disappearance of carbazole was confirmed by TLC (thin layer chromatograph), the reaction mixture was added to 2 L of methanol. This operation was carried out ten times, and the mixture was stirred in methanol at room temperature for 22 hours. The green solid was collected by suction filtration to obtain a dark green solid. The obtained solid was treated with a large sublimation purifier at 1.2 × 10 -2 torr, at a heating rate of 1 ° C./min,Purification was carried out at a sublimation temperature of 250 ° C. to obtain a white solid (yield 2.8 g, yield 11percent). Identification of the target product was carried out by 1 H-NMR (400 MHz, DMSO). A chart of 1 H-NMR is shown in FIG. 1. |
14 g | Stage #1: With iron(III) chloride In chloroform at 20℃; for 22 h; Inert atmosphere Stage #2: for 1 h; Stage #3: for 0.5 h; Reflux |
Under nitrogen flow , at room temperature, the32.0 g of cardazole, Anhydrous ferric chloride [III] 93.13g with 400 ml of chloroform mixture solution was stirred for 22h. The mixed solution wasplaced in 1000 ml of methanol, stirred for 1 hour and then filtered. Into the resultingpowder added tetrahydrofuran (600 rrd) then mixture was refluxed for 30 minutesand followed by filtration to remove the insoluble matter. After evaporation,the mixture was dissolved in 100 ml of DMI (l, 3-Dimethyl-2-Imidazolidinone)and recrystallized at 5 ° C to obtain 14.0 g of 9H, 9'H-3,3'- Dicarbazole |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
59% | With tris-(dibenzylideneacetone)dipalladium(0) In water; toluene | A mixture solution of 3-bromo-9H-carbazole (6.75 g, 27.4 mmol), 9-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole (12.15 g, 32.9 mmol), Pd2(dba)3 (0.251 g, 0.274 mmol), SPhos (0.450 g, 1.097 mmol) and K3PO4 (25.3 g, 110 mmol) in toluene (500 mL) and water (50 mL) was refluxed under nitrogen for 10 h. After cooling to room temperature, the reaction mixture was extracted with dichloromethane and washed with brine. The combined organic solutions were dried over Na2SO4, filtered, and the solvent was evaporated to yield a crude product, which was recrystallized from DCM/hexane (1/1, v/v, 1200 mL) to yield 9H,9'H-3,3'-bicarbazole (6.66 g, 59percent) as a yellow solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
5.59 g | With copper; potassium carbonate In nitrobenzene at 180℃; for 4 h; Inert atmosphere | Then under a nitrogen stream, the 14.0g of 9H, 9'H-3,3'- Dicarbazole,Iodine benzene 8.59 g, nitrobenzene 400ml, 5.72 g of copper powder with 12.44 g of potassium carbonate mixturesolution heated to 180 ° C for 4 hours. After coolingto room temperature, the nitrobenzene was removed by distillation under reducedpressure, followed by purification by silica gel chromatography, vacuum dryingto obtain 5.59g of 9-phenyl-9H, 9H-3,3-dicarbazole. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With iron(III) chloride; In chloroform; at 20℃; for 0.5h; | Carbazole (10 g, 59.8 mmol), iron (III) chloride (38.8 g, 239.3 mmol) and chloroform (200 mL) were sequentially added to a 400 mL four-necked flask and stirred at room temperature for 30 minutes.After completion of the reaction, the organic solvent was removed under reduced pressure, and the solid obtained was washed by adding methanol.The solid was collected by filtration, and then the same methanol washing was repeated twice to obtain Intermediate 3 (16.7 g, yield 84%). |
71% | With iron(III) chloride; In chloroform; at 25℃; for 3h;Inert atmosphere; | To a suspended solution of ferric chloride (FeCl3) (12.88 g, 79.85 mmol) in 100 mL of dry chloroform (CHCl3) under nitrogen atmosphere, a solution of carbazole (1) (5.55 g, 17.89 mmol) in CHCl3 (50 mL) was slowly added at 25 C. After 3 h of stirring, methanol (MeOH) (300 mL), and dichloromethane (DCM) (100 mL) were added, and the mixture extracted using distilled water (2×200 mL). Brine solution was used to wash the combined organic layers which were then dried using anhydrous sodium sulphate (Na2SO4), filtered, and the solvent was removed to dryness. Column chromatography was done to purify the desired product, using a mixture of ethyl acetate and n-hexanes. |
62% | With iron(III) chloride; In chloroform; at 20℃; | Bicarbazole (BCz) was prepared by chemical oxidation of 9H-carbazole in the presence of FeCl3. To a solution of 9H-carbazole (8.35 g, 100 mmol) in chloroform (150 ml) Iron chloride (anhydrous FeCl 3, 20 g, 120 mmol) was added thereto and stirred at room temperature for 30 minutes. The chloroform was removed from the reaction mixture and concentrated.After filtration with an excess amount of water, BCz (5.5 g, 62%) was obtained through column chromatography (hexane: ethyl acetate = 2: 1 to 1: 1). |
22% | Carbazole (12.0 g, 72.0 mmol) and anhydrous FeCl3 (47.0 g, 288 mmol) were dissolved in 240 mLof chloroform and stirred for 30 min under nitrogen. The solution was subsequently poured into alarger quantity of methyl alcohol. The precipitated green powder and zinc powder (18.7 g, 288 mmol)were dissolved in a solution of acetic acid and ethyl acetate (180 mL, 1:1) under nitrogen. The mixturewas heated at 50 C overnight. The reaction mixture was filtered and washed with hot ethyl acetate.The filtered solution was poured into water and extracted with ethyl acetate. The organics werecombined, washed with brine, and dried with sodium sulfate. After solvent removal, 5.94 g of a brownpowder was obtained. This crude product was purified via vacuum sublimation. Obtained as a whilesolid was 2.53 g (8.0 mmol, 22%) of BCz. 1H-NMR (400 MHz, DMSO-d6): delta (ppm) 11.28 (s, 2H), 8.51(s, 2H), 8.25 (d, J = 7.7 Hz, 2H), 7.81 (dd, J = 8.4 Hz, J = 1.4 Hz, 2H), 7.58 (d, J = 8.4 Hz, 2H), 7.51 (d,J = 8.1 Hz, 2H), 7.41 (t, J = 7.6 Hz, 2H), 7.19 (t, J = 7.4 Hz, 2H). 13C-NMR (100 MHz, DMSO-d6): delta (ppm)140.7, 139.2, 132.8, 126.1, 125.4, 123.6, 123.2, 120.9, 119.0, 118.6, 111.7, 111.5. | |
11% | With iron(III) chloride; In methanol; at 20℃; for 22h; | In a 300 mL eggplant flask, 20 g of iron chlorideAnd 5 g of carbazole, and the mixture was vigorously stirred.After disappearance of carbazole was confirmed by TLC (thin layer chromatograph), the reaction mixture was added to 2 L of methanol. This operation was carried out ten times, and the mixture was stirred in methanol at room temperature for 22 hours. The green solid was collected by suction filtration to obtain a dark green solid. The obtained solid was treated with a large sublimation purifier at 1.2 × 10 -2 torr, at a heating rate of 1 C./min,Purification was carried out at a sublimation temperature of 250 C. to obtain a white solid (yield 2.8 g, yield 11%). Identification of the target product was carried out by 1 H-NMR (400 MHz, DMSO). A chart of 1 H-NMR is shown in FIG. 1. |
14 g | Under nitrogen flow , at room temperature, the32.0 g of cardazole, Anhydrous ferric chloride [III] 93.13g with 400 ml of chloroform mixture solution was stirred for 22h. The mixed solution wasplaced in 1000 ml of methanol, stirred for 1 hour and then filtered. Into the resultingpowder added tetrahydrofuran (600 rrd) then mixture was refluxed for 30 minutesand followed by filtration to remove the insoluble matter. After evaporation,the mixture was dissolved in 100 ml of DMI (l, 3-Dimethyl-2-Imidazolidinone)and recrystallized at 5 C to obtain 14.0 g of 9H, 9'H-3,3'- Dicarbazole |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate; In toluene; for 8h;Inert atmosphere; Reflux; | Under argon atmosphere,To a 200 mL three-necked flask, Intermediate 3 (0.50 g, 1.50 mmol), 4-bromo-N, N'-diphenylaniline (1.07 g, 3.31 mmol), tris (dibenzylidene) dipalladium (0.05 g, 0.23 mmol), sodium tributoxide (0.43 g, 4.51 mmol) and toluene (50 mL) were added and the mixture was heated under reflux for 8 hours. After the reaction mixture was cooled to room temperature, water was added and the organic layer was recovered by a separatory funnel. After removing the organic solvent under reduced pressure, the residue was purified by silica gel column chromatography to obtain 0.47 g (yield 65%) of a white solid (Comparative Compound 1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
59% | With tris-(dibenzylideneacetone)dipalladium(0); In water; toluene; | A mixture solution of 3-bromo-9H-carbazole (6.75 g, 27.4 mmol), 9-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole (12.15 g, 32.9 mmol), Pd2(dba)3 (0.251 g, 0.274 mmol), SPhos (0.450 g, 1.097 mmol) and K3PO4 (25.3 g, 110 mmol) in toluene (500 mL) and water (50 mL) was refluxed under nitrogen for 10 h. After cooling to room temperature, the reaction mixture was extracted with dichloromethane and washed with brine. The combined organic solutions were dried over Na2SO4, filtered, and the solvent was evaporated to yield a crude product, which was recrystallized from DCM/hexane (1/1, v/v, 1200 mL) to yield 9H,9'H-3,3'-bicarbazole (6.66 g, 59%) as a yellow solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
43% | With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate; In toluene; for 24h;Inert atmosphere; Reflux; | 3.32 Grams (10 mmol) of 3,3?-bicarbazole, 6.32 g (24 mmol) of 2-bromodibenzothiophene, 3.84 g (40 mmol) of sodium tert-butoxide, 137 mg (0.15 mmol) of Pd2(dba)3, 0.3 ml (0.6 mmol) of a solution of tri-tert-butylphosphine in toluene (2.0 M), and 40 ml of toluene were loaded into a three-necked flask, and then the mixture was refluxed under a nitrogen atmosphere for 24 hours.[0250]After the completion of the reaction, 500 ml of toluene were added to the sample solution and then the mixture was refluxed in a stream of nitrogen for 1 hour. After that, the resultant was cooled to room temperature and then filtered by being passed through Celite. The filtrate was further passed through a silica gel short column. Thus, a raw material impurity component was removed. After that, the remainder was recrystallized with ethyl acetate twice. Thus, a pale brownish solid (Compound (70)) was obtained. It should be noted that the molecular weight of Compound (70) is 696.88.[0251]Identification was performed by 1H-NMR and molecular weight measurement based on FD/MS.Product amount: 3.03 gYield: 43% |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
30% | With potassium phosphate; copper(l) iodide; (S,S)-1,2-diaminocyclohexane; In 1,4-dioxane; for 20h;Reflux; Inert atmosphere; | 33.24 Grams (100 mmol) of 3,3?-bicarbazole, 29.0 g (90 mmol) of 3-bromo-9-phenylcarbazole, 63.68 g (300 mmol) of K3PO4, 3.81 g (20 mmol) of CuI, 7.2 ml (60 mmol) of trans-1,2-diaminocyclohexane, and 200 ml of 1,4-dioxane were loaded into a three-necked flask, and then the mixture was refluxed under a nitrogen atmosphere for 20 hours.[0275]After the completion of the reaction, the resultant was diluted with dioxane (500 ml) and then the diluted solution was filtered by being passed through Celite. Thus, an inorganic salt was removed. Then, the remainder was concentrated. The concentrate was purified by silica gel chromatography (hexane:dicholoromethane=5:5), and was then washed by being dispersed in methanol. Thus, a white solid (Compound (160-1)) was obtained.[0276]Identification was performed by 1H-NMR and molecular weight measurement based on FD/MS.Product amount: 17.2 gYield: 30% |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
49.7% | With potassium carbonate; In N,N-dimethyl-formamide; at 70℃; | A mixture of 3, 3?-dicarbazyl (3 g, 9 mmol), 5-chloroisophthalnitrile (2.93 g, 18 mmol) and K2CO3(4.98 g, 36 mmol) suspended in 78 mL dry DMF was stirred and heated at 70C overnight. The cooled mixture was partitioned between chloroform and water. The organic layer was separated, and the aqueous layer was extracted with chloroform. The combined organic layers were dried over MgSO4, and concentrated in vacuum. Purification of the residue by column chromatography (silica,chloroform/ethyl acetate = 10:1) afforded 2.30 g of 35IPNDCz, with a yield of 49.7%.1H NMR (500 MHz, CDCl3, TMS) delta = 7.416-7.467 (m, 4H), 7.506-7.544 (m, 4H), 7.282 (dd,J=10.5 Hz, 2H), 8.021 (s, 2H), 8.217 (s, 4H) 8.256 (d, J=8 Hz, 2H), 8.450 (s, 2H).13C NMR (125 MHz, DMSO, TMS) delta = 140.01, 138.85, 138.68, 135.02, 134.82, 133.97, 126.77,125.74, 123.98, 123.41, 121.11, 120.86, 118.62, 116.68, 114.82, 110.30, 109.96.TOF-Mass [M+] calcd.: 586.64; found, 584.04. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68.5% | With potassium carbonate; In N,N-dimethyl-formamide; at 150℃; | A mixture of 3, 3?-dicarbazyl (3 mmol, 1 g), <strong>[28442-78-6]2-<strong>[28442-78-6]chloroisophthalonitrile</strong></strong> (6 mmol, 1.8 g) and K2CO3 (1.66 g, 12 mmol) was stirred in 24 mL dry DMF and heated at 150C overnight. The cooledmixture was washed with CHCl3 and MeOH. The obtained product was concentrated in vacuum.Purification of the residue by column chromatography (silica, acetone/ethyl acetate/hexane = 1:5:5)afforded 1.20 g of 26IPNDCz, with a yield of 68.5%.1H NMR (500 MHz, CDCl3, TMS) delta =7.115 (d, J=4.5 Hz, 2H), 7.195 (d, J=8.5 Hz, 2H), 7.416 (t,J=7.5 Hz, 2H), 7.491 (t, J=7.5 Hz, 2H), 7.783-7.831 (m, 4H), 8.183 (d, J=4 Hz, 4H), 8.255 (d, J=7.5Hz, 2H), 8.455 (s, 2H).13C NMR (125 MHz, CDCl3, TMS) delta =143.23, 140.62, 139.43, 138.36, 135.90, 129.49, 126.73,126.58, 124.99, 124.56, 121.87, 121.12, 119.90, 115.75, 114.19, 109.69, 109.58.TOF-Mass [M+] calcd.: 586.64; found, 586.47. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate; In toluene;Reflux; | To a round bottom flask <strong>[1984-49-2]9H,9'H-3,3'-bicarbazole</strong> 10.0g, 3-bromo-1,1'-biphenyl 14.1g, t-BuONa 4.4g, Pd2(dba)3 1.1g, (t-Bu)3P was dissolved in 2.5ml toluene 200ml the mixture was stirred under reflux. Check the reaction by TLC and the reaction was terminated after addition of water. The organic layer was extracted with MC and purified, and the residue was filtered under reduced pressure and then recrystallized to obtain the compound 2-3 column 14.2g (yield 73%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
55% | Sodium hydride (0.07 g, 1.8 mmol) was 3 times washed with hexane and then, dried under vacuum for 2 hours. Subsequently, tetrahydrofuran (20 ml) was added thereto, and after 30 minutes, 9H,9?H-3,3?-bicarbazole (0.25 g, 0.8 mmol) was added thereto. Afier 10 minutes, Intermediate 1-2 (0.54 g, 1.7 mmol) was added thereto. Subsequently, the solution was stirred at room temperature for 10 hours, treated with magnesium sulfate by using ethylacetate to remove moisture, and then, wet-purified through a column and sublimated to obtain Dopant 1 (0.23 g). A yield was 55%.10147] Dopant 1: mass analysis (FAR) mlz 915 [(M+H)]. ?H NMR (400 MHz, CDC13): oe 8.52 (s, 2H), 8.41 (s, 2H), 8.22 (d, 2H, J=8.0 Hz), 8.14 (d, 4H, J=8.0 Hz), 8.02 (s, 2H),7.81 (d, 2H, J=6.8 Hz), 7.54-7.38 (m, 20H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90.6% | With tetrabutylammomium bromide; sodium hydroxide; In acetone; at 60℃; for 1h; | Solid NaOH (0.12 g, 3.0 mmol) was added to bicarbazole (BCz) (0.332 g, 1.0 mmol) and etrabutylammonium bromide (TBAB) (0.013 g, 0.04 mmol) dissolved in 20 mL of acetone to give a clear solution After stirring, vinylbenzyl chloride (0.35 g, 2.29 mmol) was added dropwise and the reaction was refluxed at 60 C for 1 hourThe reaction was terminated. Ethyl acetate (20 mL) was added and the organic layer was separated, washed with water, dried over magnesium sulfate and concentrated. BCzMS (0.51 g, 90.6%) was obtained through column chromatography (hexane: ethylacetate, 4: 1). |
56% | With tetrabutylammonium hydrogen sulfide; In tetrahydrofuran; at 65℃; for 24h; | (9,9?-bis(4-vinylbenzyl)-9H,9?H-3,3?-bicarbazole) (3/VyPyMCz)was prepared by the reaction of 9H,9?H-[3,3?]bicarbazole (2) with anexcess of 4-vinylbenzylchloride under basic conditions in the presenceof TBAHS phase transfer catalyst. 2.0 g (6.02 mmol) of compound 2 and2.02 g (13.24 mmol) of 4-vinylbenzylchloride were heated to reflux in50 ml of THF at 65 C. Then 1.01 g (18 mmol) of powdered KOH and acatalytic amount of TBAHS were added to the mixture, and it was refluxedfor 24 h. After thin layer chromatography (TLC) control the reactionmixture was filtered, the solvent was evaporated and the productwas purified by column chromatography with silica gel using hexane/ethyl acetate (vol. ratio 5:1) as an eluent. Yield: 1.9 g (56%) of yellowamorphous material. MS (APCI+, 20 V): 565.3 ([M +H], 100%). 1HNMR spectrum (300 MHz, CDCl3, delta, ppm): 8.47 (d, 2H, J=1.8 Hz, Ar),8.30-8.22 (m, 2H, Ar), 7.81 (dd, 2H, J1=1.8 Hz, J2=8.4 Hz, Ar),7.53-7.30 (m, 12H, Ar), 7.23-7.15 (m, 4H, Ar), 6.71 (dd, 2H,J1=11.1 Hz, J2=17.7 Hz, 2×Ph-CH=CH2), 5.74 (dd, 2H,J1=0.9 Hz, J2=17.7 Hz, Ph-CH=CH2), 5.59 (s, 4H, 2×Ph-CH2-Ar),5.24 (dd, 2H, J1=0.6 Hz, J2=10.8 Hz, Ph-CH=CH2). 13C NMRspectrum (CDCl3, delta, ppm): 141.12, 139.78, 139.94, 136.76, 136.32,133.80, 126.69, 126,67, 125.99, 125.83, 123.66, 123.30, 120.54,119.32, 119.06, 113.98, 109.15, 109.04, 46.51. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89.6% | With tetrabutylammomium bromide; sodium hydroxide; In acetone; at 60℃; for 2h; | (0.3 g, 1.0 mmol), tetrabutylammonium bromide (TBAB) (0.013 g, 0.06 mmol), NaOH (0.12 g, 3.0 mmol), (BOSBr) (0.6 g, 2.353 mmol) in acetone mL) was prepared in the same manner as BCzMS. BCzBOS (0.61 g, 89.6%) was obtained through column chromatography (Hexane: ethylacetate = 4: 1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83.6% | With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 0 - 20℃; for 3h; | N-bromosuccinimide (3.56 g, 20 mmol) in DMF (10 mL) was slowly added to a DMF (50 mL) solution of BCz (3.32 g, 10 mmol) dissolved in water at 0 C and stirred for 3 hours at room temperature. (100 mL) was added thereto, followed by extraction with CH2Cl2 (50 mL x 3). The organic layer was washed with water (150 mL x 2), dried over anhydrous Na2SO4, concentrated in vacuo and purified by column chromatography(SiO2, hexane) to obtain Br-BCz (4.1 g, 83.6%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With potassium carbonate; In dimethyl sulfoxide; at 140℃; for 12h;Inert atmosphere; | A mixture of <strong>[1984-49-2]9H,9'H-3,3'-bicarbazole</strong> (500 mg, 1.50 mmol), 4-fluoro-2-methylbenzonitrile (450 mg, 3.33 mmol) and K2CO3(0.99 g, 7.2 mmol) in dimethyl sulfoxide (DMSO) (6 mL) was stirredat 140 C for 12 h under nitrogen atmosphere. After cooling to roomtemperature, the mixture was poured into water, filtered and thenpurified by column chromatography over silica gel with CH2Cl2/petroleum ether (1: 1) as eluent to afford a white solid (760 mg,89%). 1H NMR (300 MHz, (CD3)2SO, delta ppm): 8.46 (s, 2H), 8.25 (d,J 3.0 Hz, 2H), 7.9-7.8 (m, 4H), 7.66-7.39 (m, 12H), 2.72 (s, 6H); 13CNMR (75 MHz, CDCl3, delta ppm): 144.2,141.8, 140.5, 139.2, 134.8, 134.2,127.9, 126.5, 126.0, 124.6, 124.2, 124.1, 121.0, 120.6, 119.0, 117.7, 111.1,110.0, 109.8, 20.7; M.p.: 293 C; IR (KBr, cm-1): 3051, 2214, 1603,1497, 1449, 1364, 1323, 1285, 1267, 1223, 1136, 1030, 920, 828, 803,740, 649, 578, 497, 425; MALDI-TOF (m/z): 562.215 [M+]; Anal.calcd for C40H26N4: C 85.38, H 4.66, N 9.96%; found: C 85.57, H 4.66,N 9.71%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With potassium carbonate; In dimethyl sulfoxide; at 140℃; for 12h;Inert atmosphere; | General procedure: A mixture of 9H,9'H-3,3'-bicarbazole (500 mg, 1.50 mmol), 4-fluoro-2-methylbenzonitrile (450 mg, 3.33 mmol) and K2CO3(0.99 g, 7.2 mmol) in dimethyl sulfoxide (DMSO) (6 mL) was stirredat 140 C for 12 h under nitrogen atmosphere. After cooling to roomtemperature, the mixture was poured into water, filtered and thenpurified by column chromatography over silica gel with CH2Cl2/petroleum ether (1: 1) as eluent to afford a white solid (760 mg,89%). |
90% | With potassium carbonate; In dimethyl sulfoxide; at 140℃; for 12h; | 3,3?-bicarbazole (0.50 g, 1.5 mmol), potassium carbonate (0.99 g, 7.2 mmol), <strong>[67515-59-7]3-trifluoromethyl-4-fluorobenzonitrile</strong> (0.60 g, 3.3 mmol), DMSO 6 ml, 140 Heated at for 12h.After cooling to room temperature and pouring into 200 ml of water, a large amount of solid was precipitated and stirred for 0.5 h. The white solid was obtained by suction filtration and purified by column chromatography to obtain a pale yellow solid with a yield of 90%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With potassium carbonate; In dimethyl sulfoxide; at 140℃; for 12h; | 3,3?-bicarbazole (0.50 g, 1.5 mmol), potassium carbonate (0.99 g, 7.2 mmol), 2-trifluoromethyl-4-fluorobenzonitrile (0.60 g, 3.3 mmol), DMSO 6 ml, 140 Heated at for 12h.Cool to room temperature and pour into 200ml of water to precipitate a large amount of solid and stir for 0.5h.A white solid was obtained by suction filtration and purified by column chromatography to obtain a white solid with a yield of 92%. |
90% | With potassium carbonate; In dimethyl sulfoxide; at 140℃; for 12h;Inert atmosphere; | General procedure: A mixture of <strong>[1984-49-2]9H,9'H-3,3'-bicarbazole</strong> (500 mg, 1.50 mmol), 4-fluoro-2-methylbenzonitrile (450 mg, 3.33 mmol) and K2CO3(0.99 g, 7.2 mmol) in dimethyl sulfoxide (DMSO) (6 mL) was stirredat 140 C for 12 h under nitrogen atmosphere. After cooling to roomtemperature, the mixture was poured into water, filtered and thenpurified by column chromatography over silica gel with CH2Cl2/petroleum ether (1: 1) as eluent to afford a white solid (760 mg,89%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
5.59 g | With copper; potassium carbonate; In nitrobenzene; at 180℃; for 4h;Inert atmosphere; | Then under a nitrogen stream, the 14.0g of 9H, 9'H-3,3'- Dicarbazole,Iodine benzene 8.59 g, nitrobenzene 400ml, 5.72 g of copper powder with 12.44 g of potassium carbonate mixturesolution heated to 180 C for 4 hours. After coolingto room temperature, the nitrobenzene was removed by distillation under reducedpressure, followed by purification by silica gel chromatography, vacuum dryingto obtain 5.59g of 9-phenyl-9H, 9H-3,3-dicarbazole. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
55% | With potassium carbonate; L-proline; In dimethyl sulfoxide; at 140℃; for 20h;Inert atmosphere; | 0.56 g of 3,3'-bicarbazole,1.46 g of 4- (diphenylphosphoxy) bromobenzene, 0.23 g of L-proline, 1.93 g of potassium carbonate and 7 mL of dimethylsulfoxide were placed in a 20 mL recovery flask, and nitrogen bubbling was carried out for 1 hour with stirring. After adding 0.21 g of copper iodide, the mixture was stirred at 140 C. under a nitrogen stream for 20 hours. After disappearance of 3,3'-bicarbazole was confirmed by TLC, it was cooled to room temperature, the reaction mixture was dissolved in chloroform, and insoluble matter was filtered and washed with saturated brine. After dehydration with magnesium sulfate, the solvent was distilled off under reduced pressure and purified by silica gel column chromatography (ethyl acetate: triethylamine = 100: 1) to obtain a pale yellow solid of BCzPO 4. The target product was identified by thin layer chromatography, mass spectrometry (MS), 1 H-NMR. A chart of 1 H-NMR is shown in FIG. 7, An enlarged view thereof is shown in FIG. 8, and a chart of mass spectrometry (MS) is shown in FIG. The preparation conditions for this synthesis are shown in Table 3. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
33% | With copper(l) iodide; potassium carbonate; L-proline; In dimethyl sulfoxide; at 140℃; for 18h;Inert atmosphere; | 3,3'-bicarbazole (1.33 g, 4 mmol), 4-iodophenyltriphenylmethane (3.6 g, 8 mmol), L-proline (0.46 g, 4 mmol)Potassium carbonate (6.63 g, 48 mmol) and DMSO (20 mL) were added and nitrogen bubbling was carried out for 1 hour. Then CuI (0.3 g, 1.6 mmol) was added, and the mixture was stirred at 140 C. for 18 hours under a nitrogen stream, and progress of the reaction was confirmed by TLC. After cooling to room temperature, the reaction mixture was dissolved in chloroform and washed with saturated brine. After dehydration with magnesium sulfate, the solvent was distilled off under reduced pressure and purified by silica gel column chromatography (hexane = 100 => ethyl acetate: hexane = 1: 10 => ethyl acetate: hexane = 1: 5 => ethyl acetate = 100) Purification yielded a pale yellow solid (Yield: 1.3 g, Yield: 33%). The chart of 1 H-NMR is shown in FIG. 26, the enlarged view of its aromatic region is shown in FIG. 27, and the chart of mass spectrometry (MS) is shown in FIG. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
54% | With copper; potassium carbonate; In nitrobenzene; at 170℃; for 17h;Inert atmosphere; | In a 20 mL eggplant flask, 3,3'-bicarbazole,1-Bromo-3,5-dichlorobenzene, copper powder, potassium carbonate and nitrobenzene were charged, nitrogen bubbling was carried out for 1 hour, and the mixture was stirred at 170 C. for 17 hours under a nitrogen stream. Progress of the reaction was confirmed by TLC (ethyl acetate: hexane = 1: 3) to confirm disappearance of 3,3'-bicarbazole and cooled to room temperature. The reaction mixture was dissolved in chloroform and the insoluble matter was filtered through celite. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (chloroform: hexane = 1: 1) to obtain a pale yellow solid of BCzPhCl (yield: 810 mg, yield: 54%). It was identified by mass spectrometry (MS), 1 H-NMR. A chart of 1 H-NMR is shown in FIG. 2, and an enlarged view thereof is shown in FIG. 3. Table 1 shows the preparation conditions of this synthesis.A similar experiment is shown in Table 1Run No. 2 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
51.3% | 1.00 g (3.01 mmol) of 3,3'-non-9H-carbazole and 1.66 g (12.0 mmol) of potassium carbonate were placed in a 100 ml three-necked flask, and the flask was purged with nitrogen. N, N-dimethylformamide (24.0 ml) was added to the mixture, and the mixture was stirred at room temperatureAnd stirred for 2 hours. After 1.80 g (11.1 mmol) of <strong>[28442-78-6]2-<strong>[28442-78-6]chloroisophthalonitrile</strong></strong> was added to the mixture, a nitrogen atmosphereThe resulting mixture was stirred at 150 C for 20 hours. After stirring, the solvent in the mixture was removed by distillation under reduced pressure.After removal, 100 ml of ethyl acetate and 50 ml of water were added to the mixture and stirred. After stirring, the mixtureFollowed by suction filtration to obtain a filtrate. The obtained aqueous layer of the filtrate and the organic layer were separated, and the organic layer was washed with water.After washing, magnesium sulfate was added to the organic layer and dried. After drying, the mixture was subjected to suction filtration to obtain a filtrate. The obtained filtrate was concentrated and purified by silica gel column chromatography. The developing solvent, A mixed solvent of acetone: ethyl acetate: hexane = 1: 5: 5 was used. The resulting fraction was concentrated to giveThe solid was washed with a mixed solvent of chloroform and methanol to obtain the desired pale orange powder-like solid in an amount of 0.902G, and the yield was 51.3%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
13.3% | 3.00 g (9.03 mmol) of 3,3'-9H-biscarbazole and 4.98 g (36.0 mmol) of potassium carbonate were placed in a 200 ml three-necked flask, and the flask was purged with nitrogen. N, N-Dimethylformamide (78.0 ml) was added to the mixture, and the mixture was stirred at room temperature for 2 hours under a nitrogen stream. After adding 2.93 g (18.0 mmol) of 5-fluoroisophthalonitrile into this mixture, the mixture was stirred at 70 C for 20 hours under a nitrogen atmosphere. After the stirring, the solvent in the mixture was removed by distillation under reduced pressure. After removal, 100 ml of chloroform and 50 ml of water were added to this mixture and stirred. After stirring, the mixture was subjected to suction filtration to obtain a filtrate. The obtained aqueous layer of the filtrate and the organic layer were separated, and the organic layer was washed with water. After washing, magnesium sulfate was added to the organic layer and dried. After drying, the mixture was subjected to suction filtration to obtain a filtrate. The obtained filtrate was concentrated and purified by silica gel column chromatography. As the developing solvent, a mixed solvent of chloroform: ethyl acetate = 10: 1 was used first. The resulting fraction was concentrated, and the resulting solid was recrystallized from a mixed solvent of chloroform and methanol to obtain 0.700 g of a pale orange powdery solid as a target product in a yield of 13.3%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86 mmol | With bis(tri-t-butylphosphine)palladium(0); sodium t-butanolate; In toluene; for 6h;Reflux; Inert atmosphere; | 100 mmol of compound 1-a and 220 mmol of 4-bromobiphenyl were dissolved in 1000 ml of toluene and 300 mmol of sodium tert-butoxide and 2 mmol of catalyst Pd[P(t-Bu)3]2 were added thereto, and refluxed under nitrogen for 6 hours. Then, the reaction solution was added to the reaction solution to terminate the reaction and extracted with methylene chloride. The mixture was washed with brine, the organic layer was separated, the organic solvent was removed by steaming, the crude product was passed through a column and recrystallized from dichloromethane and ethanol. Dried in vacuo to give 86 mmol of product compound 1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71 mmol | With bis(tri-t-butylphosphine)palladium(0); sodium t-butanolate; In toluene; for 6h;Reflux; Inert atmosphere; | 100 mmol of compound 2-a and 120 mmol of 4-bromobiphenyl and 120 mmol of 3-bromobiphenyl were dissolved in 1000 ml of toluene,And 300 mmol of sodium tert-butoxide and 2 mmol of catalyst Pd [P (t-Bu) 3] 2 were added thereto and refluxed under nitrogen for 6 hours. Then, the reaction solution was added to the reaction solution to terminate the reaction, and the mixture was extracted with methylene chloride. The organic layer was separated, and the organic solvent was distilled off. The crude product was passed through a column and recrystallized from methylene chloride and ethanol. 71 mmol of product compound 2. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
48% | With potassium phosphate; copper(l) iodide; trans-1,2-cyclohexanediamine; In 1,4-dioxane; for 18h;Reflux; Inert atmosphere; | General procedure: 9H,9?H-3,3-bicarbazole (1.50 g, 3.67 mmol), 4-iododibenzo [b,d]thiophene (1.48 g, 4.77 mmol), copper iodide (0.21 g, 1.10 mmol), potassium phosphate (2.34 g, 11.02 mmol) and (±)-trans-1,2-diaminocyclohexane (0.13 ml, 1.10 mmol) in 1,4-dioxane (50 ml) were refluxed under nitrogen for 18 h and cooled to room temperature. After filtering the solution, the filtrate was dried and extracted with dichloromethane and distilled water. The organic layer was dehydrated with magnesium sulfate and then dried under vacuum condition. After purification, a white solid was collected by column chromatography (dichloromethane: hexane (1: 1)). ) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With potassium phosphate; copper(l) iodide; In 5,5-dimethyl-1,3-cyclohexadiene; for 24h;Inert atmosphere; Reflux; | Under the protection of nitrogen,To 500ml of three bottles,33.7 g of compound A (100 mmol), 27.7 g of compound I (90 mmol), 3.8 g of cuprous iodide (20 mmol), 42.4 g of tripotassium phosphate (200 mmol)200 g xylene,Heated to reflux for 24 hours,TLC was tracked to no compound I.Reaction finished,Cooling to 30 ,Filter, xylene 50ml * 3 leaching,The filtrate was washed with 200 g * 3 to pH = 7,After the organic phase is dried,Normal pressure on silica gel column.After the column,Xylene 50ml * 2 eluted silica gel column,Leaching finished,The eluent and the column with the pressure combined with pressure from the solvent,De-solvent was added to 300 ml of ethanol and 50 ml of toluene mixed solution to recrystallize twice,After drying, 42.9 g of compound J,Yield: 85%HPLC: 99.0%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | With potassium phosphate; copper(l) iodide; In 5,5-dimethyl-1,3-cyclohexadiene; for 24h;Inert atmosphere; Reflux; | Under the protection of nitrogen,To 500ml of three bottles,33.2 g of compound A (100 mmol) was added,18.5 g of compound J (90 mmol),3.8 g of cuprous iodide (20 mmol),42.4 g of tripotassium phosphate (200 mmol),200 g xylene,Heated to reflux for 24 hours,TLC was tracked to no compound.Reaction finished,Cooling to 30 ,filter,Xylene 50ml * 3 leaching,The filtrate was washed with 200 g * 3 to pH = 7,After the organic phase is dried,Normal pressure on silica gel column.After the column,Xylene 50ml * 2 eluted silica gel column,Leaching finished,The eluent and the column with the pressure combined with pressure from the solvent,De-solvent was added to 300 ml of methanol and 50 ml of toluene mixed solution to recrystallize twice,After drying, 30.5 g of compound K,Yield: 74%, HPLC: 98.5%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With potassium phosphate; copper(l) iodide; In 5,5-dimethyl-1,3-cyclohexadiene; for 24h;Inert atmosphere; Reflux; | Under the protection of nitrogen,To 500ml of three bottles,33.2 g of compound A (100 mmol) was added,22.0 g of compound L (90 mmol),3.8 g of cuprous iodide (20 mmol),42.4 g of tripotassium phosphate (200 mmol),200 g of xylene, heated to reflux for 24 hours,TLC was tracked to no compound L. Reaction finished,Cooling to 30 , filtration, xylene 50ml * 3 leaching,The filtrate was washed with 200 g * 3 to pH = 7,After the organic phase is dried,Normal pressure on silica gel column.After the column,Xylene 50ml * 2 eluted silica gel column,Leaching finished,The eluent and the column with the pressure combined with pressure from the solvent,De-solvent was added to 300 ml of methanol and 50 ml of toluene mixed solution to recrystallize twice,After drying, 29.0 g of compound M,Yield: 65%, HPLC: 97.5%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With potassium phosphate; copper(l) iodide; In 5,5-dimethyl-1,3-cyclohexadiene; for 24h;Inert atmosphere; Reflux; | Under the protection of nitrogen,To 500ml of three bottles,33.2 g of compound A (100 mmol) was added,20.9 g of compound B (90 mmol),3.8 g of cuprous iodide (20 mmol),42.4 g of tripotassium phosphate (200 mmol),200 g xylene,Heated to reflux for 24 hours,TLC was tracked to no compound B.Reaction finished,Cooling to 30 ,filter,Xylene 50ml * 3 leaching,The filtrate was washed with 200 g * 3 to pH = 7,After the organic phase is dried,Normal pressure on silica gel column.After the column,Xylene 50ml * 2 Leaching column,Leaching finished,The eluent and the column with the pressure combined with pressure from the solvent,De-solvent was added to 300 ml of ethanol and 50 ml of toluene mixed solution to recrystallize twice,After drying, 34.9 g of compound C,Yield: 80%, HPLC: 98.8%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
35% | With potassium carbonate; In dimethyl sulfoxide; at 150℃; for 10h; | 1 mmol of the starting material F-5-1, 1.0 mmol of potassium carbonate and 0.5 mmol of the starting material F-5-2, Was added to 10 mL of dimethylsulfoxide, and the mixture was heated under reflux at 150 C for 10 hours. After cooling to room temperature, 200 mL of water was added to the system to precipitate a solid which was purified by column chromatography and purified by column chromatography to give a yield of 35%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
32% | General procedure: An amine (1.0 mmol), crushed KOH (1.1 mmol, 62 mg), anhydrous KF (1.0 mmol, 58 mg),and granulated calcium carbide (2.0 mmol, 130 mg) were added to a reaction tube (7 mL) with 1 mLof DMSO. After stirring at room temperature for 5 min, water (4.0 mmol, 72 L) was added,the tube was sealed, and the mixture was heated at 130 C for 4 h with vigorous stirring.After cooling to 25 C, the mixture was extracted with hexane (4 x 4 mL). Combined extractswere treated with 5% aqueous NaOH, then with brine, with water, and finally dried overNa2SO4. Concentration under reduced pressure gave the target compound. All vinylated amines wereobtained as oils except 9-vinyl-9H-carbazole (2a) (m.p. 64-65 C, lit. 64 C [42]), N,N-diphenylvinylamine(2b) (m.p. 53-54 C, lit. 52-54 C [47]), N-(beta-naphthyl)-N-phenylvinylamine (2c) (m.p. 80-81 C,lit. 70-82 C [47]), 9,9'-divinyl-<strong>[1984-49-2]9H,9'H-3,3'-bicarbazole</strong> (2m) (decomposes at 162 C), and 2-methyl-4-(4-methylpiperazin-1-yl)-10-vinyl-10H-benzo[b]thieno[2,3-e][1,4]diazepine (2n) (m.p. 188-190 C). In case of compounds 2m and 2n, methyl tert-butyl ether (MTBE) was used for extractioninstead of hexane. N-vinyl derivatives were isolated by flash column chromatography with systemhexane/MTBE (5/1) as an eluent with gradient elution. Compounds characterization is reported inthe Supplementary Materials. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In acetone; for 5h;Cooling with ice; | The intermediate product 1173Ac (5.24 g, 0.024 mol) synthesized in Example 3 and 35 mL of acetone were added toA magnetic stirrer and a constant pressure dropping funnel in a 100 ml three-necked flask were stirred at room temperature for 10 minutes.Then, 3 mL of 3,3'-bicarbazole (3.99 g, 0.012 mol) in 20 mL of acetone was added dropwise to the three-necked flask under ice-cooling for about 5 h.The reaction reached equilibrium, the solvent was removed under reduced pressure, and the crude product was purified by column chromatography to give product 4 and identified by nuclear magnetic resonance spectroscopy. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69% | With copper; potassium carbonate; In N,N-dimethyl-formamide; at 145℃;Inert atmosphere; | 3,3'-Bicarbazole (1.0 g, 3 mmol), 1-t-butyl-4-iodobenzene (2.06 mL, 11.5 mmol), copper powder(1.1 g, 17 mmol), and K2CO3 (2.4 g, 17 mmol) were dissolved in 10 mL of anhydrous DMF undernitrogen. After heating the mixture at 145 C overnight, the reaction solution was filtered through aplug of celite. The filtered solution was poured into water and extracted with chloroform. The organicswere combined, washed with brine, and dried with sodium sulfate. After solvent removal, the productwas purified via column chromatography with 1:2 (v/v) chloroform-hexane as the eluent to yield 1.23 g(2.01 mmol, 69%) of BCz-tBuPh as a white solid. For OLED devices, the product was further purifiedtwice via vacuum sublimation. The sublimation yield was 74%. Mp 295 C. 1H-NMR (400 MHz,CDCl3): delta(ppm) 8.45 (d, J = 1.4 Hz, 2H), 8.24 (d, J = 7.7 Hz, 2H), 7.77 (dd, J = 8.5 Hz, J = 1.8 Hz, 2H),7.65-7.62 (m, 4H), 7.56-7.52 (m, 6H), 7.48-7.41 (m, 4H), 7.33-7.29 (m, 2H), 1.45 (s, 18H). 13C-NMR(100 MHz, CDCl3): delta (ppm) 150.4, 141.5, 140.1, 135.0, 134.3, 126.8, 126.5, 125.9, 125.8, 123.9, 123.5, 120.4,119.8, 118.9, 110.2, 110.0, 34.8, 31.5. Anal. calcd. for C44H40N2: C, 88.55; H, 6.76; N, 4.69; found: C,88.00; H, 6.84; N, 4.80%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
52% | With copper; potassium carbonate; In N,N-dimethyl-formamide; at 145℃;Inert atmosphere; | 3,3'-Bicarbazole (1.5 g, 4.5 mmol), <strong>[20651-67-6]1-n-butyl-4-iodobenzene</strong> (2.5 mL, 18 mmol), copper powder(1.70 g, 27.1 mmol), and K2CO3 (3.73 g, 27.1 mmol) were dissolved in 10 mL of anhydrous DMF undernitrogen. After heating the mixture at 145 C overnight, the reaction solution was filtered through aplug of celite. The filtered solution was poured into water and extracted with chloroform. The organicswere combined, washed with brine, and dried with sodium sulfate. After solvent removal, the productwas purified via column chromatography with 1:1 (v/v) dichloromethane-hexane as the eluent toyield 1.41 g (2.36 mmol, 52%) of BCz-nBuPh as a white solid. For OLED devices, the product wasfurther purified twice via vacuum sublimation. The sublimation yield was 33%. Mp 146 C. 1H-NMR(400 MHz, CDCl3): delta (ppm) 8.45 (s, 2H), 8.23 (d, J = 7.7 Hz, 2H), 7.77 (dd, J = 8.5 Hz, J = 1.6 Hz, 2H),7.52-7.49 (m, 6H), 7.44-7.42 (m, 8H), 7.32-7.30 (m, 2H), 2.76 (d, J = 7.6 Hz, 4H), 1.77-1.69 (m, 4H),1.51-1.42 (m, 4H), 1.01 (t, J = 7.3 Hz, 6H). 13C-NMR (100 MHz, CDCl3): delta(ppm) 142.3, 141.5, 140.2,135.2, 134.3, 129.8, 126.9, 126.0, 125.8, 123.9, 123.5, 120.4, 119.8, 118.9, 110.1 101.0, 35.4, 33.7, 22.5, 14.1.Anal. calcd. for C44H40N2 (%): C, 88.55; H, 6.76; N, 4.69; found: C, 88.07; H, 7.00; N, 4.80%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
34% | With potassium phosphate; copper(l) iodide; trans-1,2-cyclohexanediamine; In 1,4-dioxane; for 24h;Reflux; Inert atmosphere; | Into a three-necked flask, 6.65 g (20 mmol) of the compound 1-c, 10.92 g (44 mmol) of the compound 1-b, 16.98 g (80 mmol) of K3PO4, 3.81 g (20 mmol) of CuI, 7.2 ml (60 mmol) of trans-1,2-diaminocyclohexane, and 80 ml of 1,4-dioxane were charged. The mixture was refluxed for 24 h in nitrogen atmosphere. (0306) After the reaction, the reaction solution was added with 80 ml of methanol and 80 ml of water, and then, ultrasonically washed for 10 min. The precipitate was collected by filtration, washed with methanol and water, and dried. The dried product was resolved in 1 of o-xylene under heating. Immediately after cooling to room temperature, the solution was passed through a silica gel short column to remove impurities and the eluted solution was concentrated. The concentrate was recrystallized three times from a mixed solvent of o-xylene:ethyl acetate=1:1 to obtain a white solid. (0307) The identification of the compound was made by 1H-NMR and FD/MS molecular weight measurement. The yield was 4.5 g and the percentage yield was 34%. The measured triplet energy and glass transition point are shown in Table 2. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | With copper(l) iodide; In 1,4-dioxane; for 12h;Reflux; | Intermediate 1-5 (0.75 g, 1.9 mmol), 9H,9H?-3,3?- bicarbazole (0.28 g, 0.8 mmol), copper iodide (0.19 g, 1.0 mmol), and potassium phosphate (1.07 g, 5.1 mmol) were dried under vacuum for 2 hours, and 40 ml of 1,4-dioxane was added thereto. Subsequently, (±)-trans-1 ,2-diamino cyclohexane (0.11 g, 1.0 mmol) was added thereto, and the obtained mixture was heated up, refluxed and stirred for 12 hours, cooled down to room temperature, and filtered to obtain a precipitate. The filtered precipitate was washed with ethylacetate, dichloro methane, and hexane and then, sublimated to obtain Dopant 5 (0.6 g). A yield was 79%. Dopant 5: mass analysis (FAR) mlz 948 [(M+H)]. ?H NMR (400 MHz, CDC13): oe 9.07 (d, 4H, J=8.8 Hz), 8.84 (d, 8H, J=8.4 Hz), 8.51 (s, 2H), 8.28 (d, 2H, J=7.6 Hz), 7.90-7.84 (m, 6H), 7.69-7.60 (m, 16H), 7.49 (t, 2H, J=15.6 Hz), 7.38 (t, 2H, J=15.2 Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate; In toluene; for 12h;Inert atmosphere; Reflux; | 3.3-bicarbazole (6.64 g, 20 mmol)And 4-4-bromo-phenyl-dibenzofuran (6.46 g, 22 mmol)Add in a three-necked flask,Stir and dissolve with 100 mL of toluene.Nitrogen protection followed by Pd(dba)2 (575mg, 1mmol)And sodium tert-butoxide (3.84 g, 40 mmol),Subsequently, 6 mL of a 10percent solution of tri-tert-butylphosphine toluene was added.The reaction solution was stirred and refluxed for 12 hours.After cooling, wash the reaction solution three times with 100 mL of water.Dry over anhydrous sodium sulfate,Then the solvent is removed by evaporation.The residue was purified by DCM/PE (1:10).A white solid, Comparative Compound C1-1 (8.26 g, yield 72percent) was obtained |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
58% | With copper(l) iodide; 1,10-Phenanthroline; potassium carbonate; In N,N-dimethyl-formamide; at 150 - 182℃; for 24h;Inert atmosphere; | The first compound (0.33 g, 1 mml), the second compound (1.39 g, 2.2 mml), cuprous iodide (0.02 g, 5 mml), 1,10-phenanthroline (0.02 g, 5 mml), potassium carbonate (1.8 g, 10 mml) and N,N-dimethylformamide (20 ml). Nitrogen gas was introduced into the eggplant-shaped flask, and the reaction was refluxed for 24 hours at a reaction temperature of 150 to 180 C to obtain a first mixture. After the reaction, the first mixture is allowed to reach room temperature, and the first mixture is extracted with dichloromethane several times, and after each extraction, it is washed with water to obtain an organic phase; and the organic phase is dried over anhydrous sodium sulfate, Filtration, removing the solvent by a rotary evaporation method to obtain a crude product of the bipolar host material, and purifying the crude product of the bipolar host material by silica gel column chromatography to obtain petroleum ether and dichloro Methane and ethanol were rinsed as a rinse to give 0.78 g of a white solid, i.e., the bipolar host material, yield 58%, and the resulting bipolar host material was labeled as the fourth product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With potassium carbonate; In dimethyl sulfoxide; at 140℃; for 12h; | 3,3?-bicarbazole (0.50 g, 1.5 mmol), potassium carbonate (0.99 g, 7.2 mmol),2-fluorobenzonitrile (0.39 g, 3.3 mmol), DMSO 6 ml, and heated at 140 C for 12 h.Cool to room temperature and pour into 200ml water to precipitate a large amount of solid and stir for 0.5h.A white solid was obtained by suction filtration and purified by column chromatography to obtain a white solid with a yield of 84%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With potassium carbonate; In dimethyl sulfoxide; at 140℃; for 12h; | 3,3?-bicarbazole (0.50 g, 1.5 mmol), potassium carbonate (0.99 g, 7.2 mmol), 6-methyl-2-fluorobenzonitrile (0.43 g, 3.3 mmol), DMSO 6 ml, heated at 140 C 12h.After cooling to room temperature and pouring into 200 ml of water, a large amount of solids were precipitated and stirred for 0.5 h. A white solid was obtained by suction filtration and purified by column chromatography to obtain a white solid with a yield of 85%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62.3% | With copper(l) iodide; 1,10-Phenanthroline; potassium carbonate; In N,N-dimethyl-formamide; at 160℃; for 24h;Inert atmosphere; | <strong>[1984-49-2]3-(9H-carbazol-6-yl)-9H-carbazole</strong> (0.5 g, 5 mmol), 1-(4-bromophenylsulfonyl)benzene (1.125 g, 12 mmol), potassium carbonate (1.25 g,30 mmol), cuprous iodide (0.11 g, 2 mmol), 1,10-phenanthroline(0.06 g, 2 mmol) are dissolved in 30 ml of N,N-dimethylformamide(DMF) under N2, stirring for 24 h under 160 C. After completion of thereaction, dichloromethane and water are added to the cooled mixture.The organic layer is separated and dried over Na2SO4, then concentratedin vacuo. The residue solid is purified by column chromatographyto give the product as pale yellow solid (2.08 g, 62.3%): 1H NMR (500 MHz, CDCl3: 8.43 (s, 2 H), 8.27-8.19 (m, 6 H), 8.09 (d,J=7.4 Hz, 4 H), 7.82 (d, J=8.5 Hz, 4 H), 7.77 (dd, J=8.5, 1.6 Hz,2 H), 7.67 (t, J=7.4 Hz, 2 H), 7.62 (t, J=7.6 Hz, 4 H), 7.56 (d,J=8.5 Hz, 2 H), 7.51-7.44 (m, 4 H), 7.37 (t, J=7.3 Hz, 2 H). 13C NMR(500 MHz, CDCl3, delta): 144.2, 143.7, 141.4, 138.6, 138.2, 137.6, 137.1,133.5, 128.9, 128.5, 127.6, 127.1, 126.8, 124.5, 123.9, 121.5, 116.6,115.6, 109.1. EI MS (m/z): 764.16, calcd for C48H32N2O4S2, 764.18. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72.2% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; water; toluene; at 78℃;Inert atmosphere; | 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole(1.52 g, 5mmol), 3-bromo-9H- carbazole (1.23 g, 5 mmol), K2CO3(2.09 g, 15 mmol), pd(pph3)4 (0.029 g, 0.025 mmol) are added into around-bottom flask (100 mL), then adding the mixture of toluene(18 mL), ethanol (9 mL) and ultrapure water (3 mL) under N2, themixture is stirred to reflux overnight at 78 C. After completion of thereaction, the solution is separated by rotary evaporator, methylenechloride is added to the residue solid and the organic layer is dried overNa2SO4, then concentrated in vacuo [18]. The residue solid is purifiedby column chromatography to give the product as yellow solid powder(1.198 g, 72.2%): 1H NMR (500 MHz, DMSO): delta11.26 (s, 2 H), 8.50 (s,2 H), 8.34-8.31(m, 2 H), 7.91-7.88 (m, 2 H), 7.59-7.46 (m, 6 H),7.30-7.25 (m, 2 H). EI MS (m/z): 333.35, calcd for C24H16N2, 332.13. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
51.2 g | With tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate at 130℃; Inert atmosphere; | 3 Preparation of intermediate M57-2: At room temperature, M57-1 (90g, 125mmol, 2.5eq),3,3-Liancarbazole (16.65g, 50mmol, 1eq),Pd2(dba)3 (2.54g, 2.5mmol, 0.05eq),s-Phos (2.05g, 5mmol, 0.1eq), sodium tert-butoxide (21.6g, 225mmol, 4.5eq), xylene (500ml) were added to a 1000ml single-necked flask, filled with nitrogen three times, heated to 130°C and reacted overnight . The reaction solution was cooled to room temperature, mixed with Celite and filtered. Concentrate the filtrate, add dichloromethane to dissolve and mix with silica gel to concentrate, and column chromatography (PE:EA=25:1), the product Rf=0.55. Column chromatography obtained 65 g of crude gray solid product, which was boiled and washed with ethanol for 3 hours to obtain 51.2 g of white solid product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate In o-xylene at 150℃; for 12h; Inert atmosphere; | 3 Synthesis Example 3: Synthesis of Donor A19 This example is basically the same as Synthesis Example 1, but the difference is: in this example, A59-1 needs to be replaced by 1/2 substance (mol) of A19-1, and 3-bromo-9,9 '-Spirobifluorene was replaced with 4-bromotetraphenylsilane in equivalent amounts.The final product A19 (0.9g, yield 90%, purity 99.53% by HPLC analysis). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate In o-xylene at 150℃; for 12h; Inert atmosphere; | 4 Under the protection of nitrogen, add A24-1 (0.82g, 2mmol), 3-bromo-9,9-diphenylfluorene (0.79g, 2mmol) in a 250ml round bottom flask, and use o-xylene (80mL) as solvent, add S-phos (49.3mg, 0.12mmol), sodium tert-butoxide (0.58g, 6mmol) and Pd(dba)3 (55mg, 0.06mmol) as catalysts, heat to reflux for 12 hours, add ethanol after cooling to precipitate a white solid, A24-2 was obtained by filtration, which was directly used in the next reaction. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate In o-xylene at 150℃; for 12h; Inert atmosphere; | 2 Synthesis Example 2: Synthesis of Donor A23 This example is basically the same as Synthesis Example 1, and the difference is that: In this example, A59-1 needs to be replaced with 1/2 of the substance (mol) of A23-1. The final product A23 (0.8g, yield 83%, purity 99.46% by HPLC analysis). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
48% | With copper(l) iodide; 1,10-Phenanthroline In N,N-dimethyl-formamide at 140℃; for 24h; Inert atmosphere; | Synthesis of (9H, 9′H-[3,3′-bicarbazole]-9,9′-diylbis (4,1-phenylene))bis (dibenzo [b,d]thiophen-2-ylmethanone) (2DBT-BZ-2Cz). DBT-BZ-Br (2.0g, 5.45mmol), 9H, 9′H-3,3′-bicarbazole (BCz, 0.83g, 2.5mmol), cuprous iodine (0.1g, 5mmol), potassium phosphate (1.38g, 10mmol) and 1,10-phenanthroline (0.1g, 5mmol) were dissolved in 50mL solution of N, N-dimethylformamide and refluxed at 140°C temperature for 24h under nitrogen. After the reaction finished, reaction mixture was cooled to room temperature and poured into a large quantity of saturated salt solution. The precipitated organic substance was pumped out and filtered, and the crude product was purified by silica gel column chromatography (the stationary phase was silica gel, the eluent was petroleum ether and ethyl acetate 1:5). The final product was yellow solid powder in 48% yield (1.08g, 1.2mmol). 1H NMR (600MHz, CDCl3, δ): 8.67 (s, 2H), 8.43 (s, J=8.5Hz, 2H), 8.20-8.22 (m, 4H), 8.10-8.11 (d, J=7.8Hz, 4H), 7.96 (s, 4H), 7.85-7.86 (m, 2H), 7.77-7.78 (m, 6H), 7.61-7.62 (d, J=8.4Hz, 2H), 7.54-7.56 (d, J=8.4Hz, 2H), 7.42-7.48 (m, 6H), 7.31-7.33 (m, 2H). 13C NMR (150MHz, CDCl3, δ): 194.35, 143.33, 140.70, 139.75, 138.78, 138.47, 135.39, 134.64, 134.14, 133.81, 132.80, 130.95, 127.11, 126.54, 125.42, 125.28, 125.04, 123.97, 123.54, 123.05, 122.55, 122.00, 121.71, 121.06, 120.46, 119.76, 119.61, 118.05, 109.15, 108.98, 99.52. MS (MALDI-TOF) [m/z]: calcd for C62H36N2O2S2, 904.22; found, 905.10. Anal. Calcd. for C62H36N2O2S2: C, 82.28; H, 4.01; N, 3.10. Found: C, 82.30; H, 3.98; N, 3.10. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
46% | With copper(l) iodide; 1,10-Phenanthroline In N,N-dimethyl-formamide at 140℃; for 24h; Inert atmosphere; | Synthesis of (9H, 9′H-[3,3′-bicarbazole]-9,9′-diylbis (4,1-phenylene))bis (dibenzo [b,d]thiophen-2-ylmethanone) (2DBT-BZ-2Cz). General procedure: DBT-BZ-Br (2.0g, 5.45mmol), 9H, 9′H-3,3′-bicarbazole (BCz, 0.83g, 2.5mmol), cuprous iodine (0.1g, 5mmol), potassium phosphate (1.38g, 10mmol) and 1,10-phenanthroline (0.1g, 5mmol) were dissolved in 50mL solution of N, N-dimethylformamide and refluxed at 140°C temperature for 24h under nitrogen. After the reaction finished, reaction mixture was cooled to room temperature and poured into a large quantity of saturated salt solution. The precipitated organic substance was pumped out and filtered, and the crude product was purified by silica gel column chromatography (the stationary phase was silica gel, the eluent was petroleum ether and ethyl acetate 1:5). The final product was yellow solid powder in 48% yield (1.08g, 1.2mmol). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With copper; potassium carbonate In N,N-dimethyl-formamide for 18h; Reflux; Inert atmosphere; | 5 Preparation of Intermediate E1: In a 100 ml two-necked flask under a nitrogen atmosphere, 3,3'-bicarbazole (10mmol), 4'-bromo-4-iodo-1,1'biphenyl (10 mmol) ), potassium carbonate (20 mmol), copper powder (40 mmol) and DMF (50ml), heated to reflux for 18h. After the reaction, the reaction solution was filtered, and then extracted and separated. Then, the reaction solution was separated and purified with a silica gel column, and the solvent was removed by rotary evaporation to collect the product. Finally, the intermediate E1 was obtained by vacuum drying at room temperature for 12 h, weighed, and yield About 91%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With copper; potassium carbonate In N,N-dimethyl-formamide for 18h; Reflux; Inert atmosphere; | 6 Preparation of Intermediate F1: In a 100 ml two-necked flask under a nitrogen atmosphere, 3,3'-bicarbazole (10mmol), 4'-bromo-(1,1'biphenyl)-4-methanol ( 10 mmol), potassium carbonate (20 mmol), copper powder (40 mmol) and DMF (50ml), heated to reflux for 18h. After the reaction, the reaction solution was filtered, and then extracted and separated. Then, the reaction solution was separated and purified with a silica gel column, and the solvent was removed by rotary evaporation to collect the product. Finally, the intermediate F1 was obtained by vacuum drying at room temperature for 12 h, weighed, and yield About 88%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With copper; potassium carbonate In N,N-dimethyl-formamide for 18h; Inert atmosphere; Reflux; | 2; 4 Preparation of Intermediate B1: In a 100 ml two-necked flask under a nitrogen atmosphere, 3,3'-bicarbazole (9.78 mmol) and 4'-bromo-3-iodo-1,1'biphenyl (9.78 mmol) were added to a 100 ml two-necked flask. mmol), potassium carbonate (20 mmol), copper powder (40 mmol) and DMF (50 ml), heated to reflux for 18h. After the reaction, the reaction solution was filtered, and then extracted and separated. Then, the reaction solution was separated and purified with a silica gel chromatographic column, and the solvent was removed by rotary evaporation to collect the product. Finally, it was vacuum dried at room temperature for 12 h.Intermediate B1 is obtained, weighed, and the yield is about 80%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | With trifluorormethanesulfonic acid; hexadeuterobenzene at 50℃; | 7.1; 11.1 1) Preparation of compound 2-106-1 In a one neck round bottom flask, 9H,9'H-3,3'-biscarbazole 10g (0.030 mol), triflic acid 34g (0.023 mol),a mixture of 100 ml of D6-benzene was refluxed at 50°C. After cooling, it was extracted with dichloromethane and dried over MgSO4. Separation by column chromatography to obtain 7.07 g of intermediate 2-106-1 (yield: 68%) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With tripotassium phosphate tribasic; copper (I) iodide; trans-1,2-Diaminocyclohexane In 1,4-dioxane at 125℃; for 8h; | 6.1 1) Preparation of compound 2-98-1 In a one neck round bottom flask 9H,9'H-3,3'-bicarbazole 10g (0.030 mol), 4-bromo-1,1'-biphenyl-2,2',3,3',4',5,5' ,6,6'-D9 (C) 7.26 g (0.030 mol), CuI 0.57 g (0.003 mol), trans-1,2-diaminocyclohexane 0.34 g (0.003 mol), K3PO4 12.7 g (0.06 mol) After dissolving in 100 ml of 1,4-dioxane, it was refluxed at 125° C. for 8 hours. After the reaction was completed, it was cooled, extracted with dichloromethane, and dried over MgSO4. The separated organic layer was concentrated under reduced pressure and separated by column chromatography to obtain 13.92 g of compound 2-98-1 (yield: 94%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With tripotassium phosphate tribasic; copper (I) iodide; trans-1,2-Diaminocyclohexane In 1,4-dioxane at 125℃; for 8h; | 10.1 1) Preparation of compound 3-106-1 9H,9'H-3,3'-bicarbazole 10g (0.030 mol), 1-bromobenzene-2,3,4,5,6-D5 in a one neck round bottom flask (B) 4.86 g (0.030 mol), CuI 0.57 g (0.003 mol), trans-1,2-diaminocyclohexane 0.34 g (0.003 mol), K3PO4 12.7 g (0.06 mol) 1,4-dioxane 100 ml After dissolving in , it was refluxed at 125 °C for 8 hours. After completion of the reaction, the mixture was cooled, extracted with dichloromethane, and dried over MgSO4. The elapsed organic layer was concentrated under reduced pressure and separated by column chromatography to obtain 10 g of compound 3-106-1 (yield: 81%). |
Tags: 1984-49-2 synthesis path| 1984-49-2 SDS| 1984-49-2 COA| 1984-49-2 purity| 1984-49-2 application| 1984-49-2 NMR| 1984-49-2 COA| 1984-49-2 structure
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