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CAS No. : | 38303-35-4 | MDL No. : | MFCD00230868 |
Formula : | C16H8Br2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | JBLQSCAVCHTKPV-UHFFFAOYSA-N |
M.W : | 360.04 | Pubchem ID : | 181577 |
Synonyms : |
|
Num. heavy atoms : | 18 |
Num. arom. heavy atoms : | 16 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 0.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 85.55 |
TPSA : | 0.0 Ų |
GI absorption : | Low |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | Yes |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -3.95 cm/s |
Log Po/w (iLOGP) : | 3.23 |
Log Po/w (XLOGP3) : | 6.41 |
Log Po/w (WLOGP) : | 6.11 |
Log Po/w (MLOGP) : | 5.9 |
Log Po/w (SILICOS-IT) : | 6.08 |
Consensus Log Po/w : | 5.54 |
Lipinski : | 1.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 1.0 |
Muegge : | 2.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -6.77 |
Solubility : | 0.0000614 mg/ml ; 0.00000017 mol/l |
Class : | Poorly soluble |
Log S (Ali) : | -6.2 |
Solubility : | 0.000226 mg/ml ; 0.000000627 mol/l |
Class : | Poorly soluble |
Log S (SILICOS-IT) : | -8.24 |
Solubility : | 0.00000207 mg/ml ; 0.0000000057 mol/l |
Class : | Poorly soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 2.0 |
Synthetic accessibility : | 1.53 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302 | 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 |
---|---|---|
71.1% | With bromine In chloroform for 4 h; Inert atmosphere; Reflux | 58 g (0.287 mol) of pyrene are initially introduced in 1750 ml of chloroform. A solution of 31 ml (0.609 mol) of Br2 in 250 ml of chloroform is subsequently added dropwise at RT with exclusion of light. The reaction mixture is heated under reflux for 4 h. After cooling, the precipitated solid is filtered off with suction and washed with ethanol and dried. The solid obtained is recrystallised 3 times from CHCI3. Yield: 1 ,6- dibromopyrene 73.4 g (0.201 mol), 71.1percent of theory, and 1 ,8-dibromopyrene 20.6 g (0.06 mol), 20percent of theory. |
50% | With bromine In tetrachloromethane at 20 - 25℃; for 54 h; | The solution of 10 ml(31.19 g, 0.195 mol) of bromine in 500 ml of anhydrous CCl4 was addeddropwise to the solution of 20.2 g (0.1 mol) pyrene in 500 ml of anhydrousCCl4 for 6 h at 20–25 °C. Once the addition of bromine was completed,the mixture was kept at the same temperature for 48 h. The precipitate of1,6-dibromopyrene was filtered off, washed with hexane and methanoland dried in vacuo over P2O5, yield 9.02 g (25percent). The filtrate wasconcentrated, the solid residue was recrystallized from toluene–hexanegiving 1,8-dibromopyrene, yield 17.9 g (50percent).For 1,8-dibromopyrene: 1H NMR, δ: 7.97 (s, 2 H), 7.98 (d, 2H, J 8.5 Hz),8.22 (d, 2H, J 8.2 Hz), 8.46 (s, 2H). IR (ν/cm–1): 3102, 3038, 1936,1882, 1597, 1582 (C=C), 1481, 1455, 1427, 1416, 1310, 1295, 1234,1202, 1163, 1146, 1118, 1026, 976, 845, 836, 819, 784, 777, 768, 704.MS, m/z: 360 [M]+.For 1,6-dibromopyrene: 1H NMR, δ: 8.18 (d, 2H, J 8.2 Hz), 8.10 (d,2H, J 9.2 Hz), 8.26 (d, 2H, J 8.2 Hz), 8.44 (d, 2H, J 9.2 Hz). IR (ν/cm–1):3038, 1600, 1581 (C=C), 1482, 1453, 1427, 1417, 1287, 1234, 1202,1162, 1091, 1052, 1025, 979, 881, 852, 836, 818, 703. MS, m/z: 360 [M]+. |
14% | With bromine In chloroform at 20℃; for 5 h; | Bromine (10.0 mL, 195 mmol) in CHCl3(500 mL) was dropped into a solution of pyrene (20.0 g, 98.9 mmol) inCHCl3 (500 mL) over 5 h while stirring. The precipitate was collectedafter 12 h and recrystallized from xylene to give compound 5 (5.01 g,14percent) and compound 6 (2.17 g, 6percent). Compound 5: 1H NMR (300 MHz,CDCl3): δ = 8.46 (d, 2H), 8.26 (d, 2H), 8.11 (d, 2H), 8.05 (d, 2H);EI + -Mass: 360. Compound 6: 1H NMR (300 MHz, CDCl3): δ= 8.56 (s,2H), 8.27 (d, 2H), 8.05 (m, 4H); EI + -Mass: 360. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
28% | With N2; bromine In tetrachloromethane | First, pyrene (10 g, 0.0049 mol) is dissolved into CCl4 (300 mL) in a 3-necks-r.b.f. And, Br2(17.38 g, 0.108 mol) CCl4(50 mL) are put into a dropping funnel provided at the round-floor flask and slowly dropped in the round-floor flask for 4 hours. N2 is added to and HBr is removed from the solution. When the process is finished, the solution is stirred under N2 current for one hour and formed sediment is filtered. When the sediment is recrystallized by toluene, a green solid matter (6.05 g, 34percent) of 1,6-Dibromopyrene and a white solid matter of 1,8-Dibromopyrene (5 g, 28percent) are obtained. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 85% 2: 15% | With carbon disulfide; bromine at 20℃; for 17h; | |
1: 85% 2: 15% | With carbon disulfide; bromine at 20℃; for 17h; | |
1: 71.1% 2: 20% | With bromine In chloroform for 4h; Inert atmosphere; Reflux; | Intermediate 1: Synthesis of 1,6- and 1,8-dibromopyrene 58 g (0.287 mol) of pyrene are initially introduced in 1750 ml of chloroform. A solution of 31 ml (0.609 mol) of Br2 in 250 ml of chloroform is subsequently added dropwise at RT with exclusion of light. The reaction mixture is heated under reflux for 4 h. After cooling, the precipitated solid is filtered off with suction and washed with ethanol and dried. The solid obtained is recrystallised 3 times from CHCI3. Yield: 1 ,6- dibromopyrene 73.4 g (0.201 mol), 71.1% of theory, and 1 ,8-dibromopyrene 20.6 g (0.06 mol), 20% of theory. |
1: 50% 2: 25% | With bromine In tetrachloromethane at 20 - 25℃; for 54h; | 1,8-Dibromopyrene and 1,6-dibromopyrene The solution of 10 ml(31.19 g, 0.195 mol) of bromine in 500 ml of anhydrous CCl4 was addeddropwise to the solution of 20.2 g (0.1 mol) pyrene in 500 ml of anhydrousCCl4 for 6 h at 20-25 °C. Once the addition of bromine was completed,the mixture was kept at the same temperature for 48 h. The precipitate of1,6-dibromopyrene was filtered off, washed with hexane and methanoland dried in vacuo over P2O5, yield 9.02 g (25%). The filtrate wasconcentrated, the solid residue was recrystallized from toluene-hexanegiving 1,8-dibromopyrene, yield 17.9 g (50%).For 1,8-dibromopyrene: 1H NMR, δ: 7.97 (s, 2 H), 7.98 (d, 2H, J 8.5 Hz),8.22 (d, 2H, J 8.2 Hz), 8.46 (s, 2H). IR (ν/cm-1): 3102, 3038, 1936,1882, 1597, 1582 (C=C), 1481, 1455, 1427, 1416, 1310, 1295, 1234,1202, 1163, 1146, 1118, 1026, 976, 845, 836, 819, 784, 777, 768, 704.MS, m/z: 360 [M]+.For 1,6-dibromopyrene: 1H NMR, δ: 8.18 (d, 2H, J 8.2 Hz), 8.10 (d,2H, J 9.2 Hz), 8.26 (d, 2H, J 8.2 Hz), 8.44 (d, 2H, J 9.2 Hz). IR (ν/cm-1):3038, 1600, 1581 (C=C), 1482, 1453, 1427, 1417, 1287, 1234, 1202,1162, 1091, 1052, 1025, 979, 881, 852, 836, 818, 703. MS, m/z: 360 [M]+. |
1: 14% 2: 6% | With bromine In chloroform at 20℃; for 5h; | Compounds 5 and 6. Bromine (10.0 mL, 195 mmol) in CHCl3(500 mL) was dropped into a solution of pyrene (20.0 g, 98.9 mmol) inCHCl3 (500 mL) over 5 h while stirring. The precipitate was collectedafter 12 h and recrystallized from xylene to give compound 5 (5.01 g,14%) and compound 6 (2.17 g, 6%). Compound 5: 1H NMR (300 MHz,CDCl3): δ = 8.46 (d, 2H), 8.26 (d, 2H), 8.11 (d, 2H), 8.05 (d, 2H);EI + -Mass: 360. Compound 6: 1H NMR (300 MHz, CDCl3): δ= 8.56 (s,2H), 8.27 (d, 2H), 8.05 (m, 4H); EI + -Mass: 360. |
With tetrachloromethane; bromine | ||
With bromine In chloroform | ||
With mono(N,N,N-trimethylbenzenaminium) tribromide; zinc(II) chloride In methanol; dichloromethane at 20℃; | ||
With bromine In dichloromethane | ||
With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione In dichloromethane at 20℃; for 1h; | ||
With bromine In tetrachloromethane at 20℃; for 2h; Inert atmosphere; | ||
With bromine In tetrachloromethane | ||
With hydrogen bromide; dihydrogen peroxide In methanol; diethyl ether Inert atmosphere; | ||
With bromine In dichloromethane | ||
With hydrogen bromide; dihydrogen peroxide In methanol; diethyl ether Inert atmosphere; Overall yield = 87.4 %; | ||
With bromine In tetrachloromethane at 20℃; | 4.2.11. Synthesis of 1,6- and 1,8-dibromopyrenes (9, 10) Accordingto the literature,14 pyrene (2.00 g, 9.80 mmol) was reacted with Br2 (3.18 g, 19.9 mmol) in CCl4 (60 ml) at room temperature. The suspension was filtered, and the remaining solid was dissolved in chloroform and washed with Na2S2O3 aq. The organic layer wasdried over anhyd Na2SO4 and concentrated to give a white solid. The composition can be determined by 1H NMR analysis, such as 9/101.1:1, and used to the next reaction without separation (Recrystallization of the mixture from chloroform afforded a 9 enriched mixture (0.78 g, 9: 19.1%, 10: 2.8%).). | |
With bromine In tetrachloromethane at 20℃; | 4.2.11. Synthesis of 1,6- and 1,8-dibromopyrenes (9, 10).14 According to the literature,14 pyrene (2.00 g, 9.80 mmol) was reacted with Br2(3.18 g, 19.9 mmol) in CCl4 (60 ml) at room temperature. The suspension was filtered, and the remaining solid was dissolved in chloroform and washed with Na2S2O3 aq. The organic layer was dried over anhyd Na2SO4 and concentrated to give a white solid. The composition can be determined by 1H NMR analysis, such as 9/10 = 1.1:1, and used to the next reaction without separation (Recrystallization of the mixture from chloroform afforded a 9 enriched mixture (0.78 g, 9: 19.1%, 10: 2.8%).). | |
With bromine In tetrachloromethane | ||
With bromine In dichloromethane at 20℃; | ||
With tetrachloromethane; bromine at 20℃; for 17h; | ||
With hydrogen bromide; dihydrogen peroxide In methanol; diethyl ether; water at 20℃; for 24h; Inert atmosphere; Overall yield = 74 percent; Overall yield = 8 g; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 53 % Spectr. 2: 44 % Spectr. 3: 3 % Spectr. | With bromine In dichloromethane for 5h; Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In toluene for 36h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium butanolate In toluene |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium butanolate In N,N-dimethyl-formamide |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
20 mg | With sodium hypochlorite; potassium bromide In methanol for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: n-BuONa / toluene 2: KI; CuI / dimethylformamide |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: n-BuONa / dimethylformamide 2: NBS / CH2Cl2 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: n-BuONa / dimethylformamide 2: NBS / CH2Cl2 3: KI; CuI / dimethylformamide |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: n-BuONa / toluene 2: KI; CuI / dimethylformamide 3: Ba(OH)2 / Pd(PPh3)4 / 1,2-dimethoxy-ethane; H2O |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: n-BuONa / dimethylformamide 2: NBS / CH2Cl2 3: KI; CuI / dimethylformamide 4: Ba(OH)2 / Pd(PPh3)4 / 1,2-dimethoxy-ethane; H2O |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 70 percent / aq. K2CO3; Pd(PPh3)4 / toluene / 36 h / Heating 2: 82 percent / Br2 / CHCl3 / 10 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 70 percent / aq. K2CO3; Pd(PPh3)4 / toluene / 36 h / Heating 2: 82 percent / Br2 / CHCl3 / 10 h / 20 °C 3: 100 percent / various solvent(s) / 3 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: N2H4*H2O / Raney-Ni 2: (i) NaNO2, aq. H2SO4, DMF, (ii) CuBr, KBr, aq. HBr |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: (i) NaNO2, aq. H2SO4, DMF, (ii) CuBr, KBr, aq. HBr 2: N2H4*H2O / Raney-Ni 3: (i) NaNO2, aq. H2SO4, DMF, (ii) CuBr, KBr, aq. HBr |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With n-butyllithium In diethyl ether; hexane (N2); using Schlenk techniques; addn. of n-butyllithium (2 equiv.) in hexane to stirred soln. of 1,8-bromopyrene (1 equiv.) in Et2O at 0°C for 10 min; addn. of Au(PPh3)Cl (2 equiv.); warming to room temp.; stirring for 2 h; addn. of CH2Cl2; filtration, concn., addn. of hexane; pptn., recrystn. by layering of hexane onto CH2Cl2 soln.; elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
53% | In toluene (N2); using Schlenk techniques; addn. of soln. of 1,8-dibromopyrene to soln. of Pt(PEt3)4 (2 equiv.) in toluene; stirring for 18 h at room temp.; removal of solvent; redissolving in min. volume of CH2Cl2; addn. of coldhexane; pptn., recrystn. from vapor diffusion of Et2O into CH2Cl2 soln. ; elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
28% | With N2; bromine In tetrachloromethane | 1 (1) First, pyrene (10 g, 0.0049 mol) is dissolved into CCl4 (300 mL) in a 3-necks-r.b.f. And, Br2(17.38 g, 0.108 mol) CCl4(50 mL) are put into a dropping funnel provided at the round-floor flask and slowly dropped in the round-floor flask for 4 hours. N2 is added to and HBr is removed from the solution. When the process is finished, the solution is stirred under N2 current for one hour and formed sediment is filtered. When the sediment is recrystallized by toluene, a green solid matter (6.05 g, 34%) of 1,6-Dibromopyrene and a white solid matter of 1,8-Dibromopyrene (5 g, 28%) are obtained. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium carbonate In water; toluene | C.A Comparative Example A Comparative Example A This comparative example illustrates the preparation of 1,8-Bis-(4-naphthalen-1-yl-phenyl)-pyrene, Comparative X. This comparative compound is the non-deuterated analog of Compound A3. Into a RBF (500 mL) was added 1,8-dibromopyrene (10 g, 27.6 mmol), 3-(2-naphthenylphenylboronic acid (16.5 g, 66.3 mmol), followed by the addition of toluene (300 mL). The mixture was purged with N2 for 10 min. Then Na2CO3 (14.6 g, 138 mmole) dissolved in the water (70 mL) was added. The mixture was continued to be purged with N2 for 10 min. A catalytic amount of Pd(PPh3)4 (0.16 g) was added. The mixture was refluxed for 4 h. First, a clear solution was formed (in about 2 h). Then 2 h later a light white precipitate was formed. Continued reflux overnight. A slightly white precipitate was formed. Filtered through silica pad at 70-90° C. to remove black Pd. After concentration, the solid was slurried with hot THF/Acetone(100 ml/100 ml) for 12 hrs. Filtered and washed with THF and dried. An off-white powder was formed (11.55 g, yield: 68.8%). Further purification of the compound by train submission affords 7.4 g pure compound (purity 99.9%). The 1H NMR spectrum was consistent with the structure of Comparative X. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine; tris-(o-tolyl)phosphine; bis(dibenzylideneacetone)-palladium(0) In toluene; acetonitrile at 111℃; for 16h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With bromine In tetrachloromethane at 20℃; for 12h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 52% 2: 30% | With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; triphenylphosphine In toluene at 80℃; for 3h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran; diethylamine at 65℃; for 21h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
41% | With sodium periodate In dichloromethane; water; acetonitrile | S.9 Synthesis Example 9 Synthesis Example 9 1,8-dibromo-pyrene-4,5,9,10-tetraone (hereinafter referred to as compound 9) represented by the following formula (29) was synthesized by the following method. 1,8-dibromopyrene (392 mg, 0.98 mmol), sodium periodate (2.142 g, 10 mmol), and ruthenium chloride hydrate (22 mg, 0.11 mmol) were added to a mixed solvent of acetonitrile (20 mL) and water (4 mL), and the reaction liquid was stirred at 60° C. for 80 minutes. The reaction liquid was returned to room temperature, and then the reaction liquid was poured into water (100 ml). An organic substance was extracted therefrom by using methylene chloride (20 ml, 3 times). The extracted organic substance was washed with brine, and then sodium sulfate was added to the obtained extract. Thereafter, sodium sulfate was removed from the extract by filtration, the extract was sent through a short column, and the solvent was removed under reduced pressure. Thereby, 1,8-dibromo-pyrene-4,5,9,10-tetraone (170 mg, yield 41%) was obtained as a yellow solid. A 1H NMR analysis, a mass analysis, and an infrared spectroscopic analysis were conducted thereon to find the following results. 1H NMR (400 MHz, CDCl3)•7.99 (d, J=8.4 Hz, 2H), 8.28 (d, J=8.4 Hz, 2H). HRMS (EI) m/z calcd for C14H4Br2O4: 417.8476, found 417.8472. IR (solid): (cm-1) 1678, 1550, 1404, 1315, 1253, 1072, 910, 829. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In dichloromethane; at 20℃; for 1h; | A solution of 1,3-dibromo-5,5-dimethylhydantoin (DBMH) (308 mg, 1.1 mmol) in dry CH2Cl2 (10 mL) was added to a solution of pyrene (252 mg, 1.00 mmol) in dry CH2Cl2 (40 mL) and stirred at room temperature for 1 h [22]. The mixture was poured into water (50 mL) and extracted with dichloromethane (200 mL). The extract was washed well with water, dried (MgSO4), and evaporated under reduced pressure to yield crude products. The crude products were successfully washed with CH2Cl2 (15 mL) to give a mixture of 1,6-di- and 1,8-dibromopyrene 3 and 4 as an orange-yellow solid (398 mg, 97%); m.p.123-124 C. Separation of 1,6-di- and 1,8-dibromopyrene 3 and 4 was reported in the literature (m.p. 230-231 C for 3 and m.p. 210-211 C for 4) [23]. However, several attempted separations of the mixture of 3 and 4 into each pure failed. The mixture of isomers of 1,6-di- and 1,8-dibromopyrene (3 and 4) was directly used to carry out next Buchwald-Hartwig amination reaction. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / 1,4-dioxane / 72 h / 60 °C 2: tetrakis(triphenylphosphine) palladium(0); tetrabutylammomium bromide; sodium carbonate / toluene / 24 h / 110 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / 1,4-dioxane / 72 h / 60 °C 2.1: tetrakis(triphenylphosphine) palladium(0); tetrabutylammomium bromide; sodium carbonate / toluene / 24 h / 110 °C / Inert atmosphere 3.1: hydrogen bromide / 3 h / 20 °C 3.2: aliquat / 24 h / 130 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
40% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane at 60℃; for 72h; | 1 Synthesis of [1-bromo-8-(4-methoxyphenyl)]pyrene (2) A mixture of 4-methoxybenzene boronic acid (0.4 g, 2.6 mmol), (1) (1 g, 2,8 mmol), Pd(PPh3)4 (0.06 g, 0.05 mmol) and dry potassium carbonate (1.6 g, 11.2 mmol) in dry 1,4-dioxane (40 mL) was stirred, under argon for 72 h at 60 °C. The reaction mixture was poured into a solution of ice with concentrated hydrochloric acid (3:1). The organic phase was extracted with dichloromethane, dried over anhydrous sodium sulfate and evaporated. The residue was purified by column chromatography, with the eluent n-hexan:CH2Cl2 (3:1). Yield 0.43 g (40%), m.p.: 141 °C. FT-IR (νmax/cm-1): 3041 (ArC-H), 2961, 2928, 2905, 2834 (C-H, CH3), 1606, 1569 (ArC=C), 1517 (ArC-C), 1261, 1240 (ArC-O), 1100 (CH3-O), 661 (ArC-Br). 1H NMR (CDCl3, ppm) δ: 7.11-8.44 (m, 12H, ArCH), 3.94 (s, 3H, OCH3); {1H}13C NMR (CDCl3, ppm) δ: 130.13, 130.06, 128.99, 128.30, 128.24, 127.72, 127.02, 126.96, 126.69, 125.80, 125.73, 125.70, 125.47, 125.37, 125.18, 125.17, 113.97, 109.98, 55.42. Elemental analysis, Found: C 71.05, H 3.78; C23H15BrO (387) requires: C 71.33, H 3.90%. MS (MALDI) m/z (%): 388 (100) [M+H]+. |
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With bromine In tetrachloromethane | ||
With bromine In dichloromethane | ||
With bromine In tetrachloromethane |
With bromine In nitrobenzene at 100℃; for 6h; Microwave irradiation; UV-irradiation; | 1.A; 2.A; 3.A; 4.A; 5.A; 6.A; 7.A; 8A; 9.A; 10.A; 11.A; 12.A; 13.A; 14.A A. Bromination reaction of pyrene: Dissolve 10mmol of pyrene in 50mL of nitrobenzene, place it in a 100mL single-neck bottle, and gradually add 30mmol of liquid bromine at room temperature. After the addition,Move the 100mL single-necked flask into a microwave reactor with laser and ultraviolet irradiation at atmospheric pressure and reflux device,Irradiate the solution with a Nd:YAG solid-state pulsed laser for 6h, the laser parameter is 1.06μm,The pulse width is 1.2ms, the spot diameter is 0.2mm, the repetition frequency is 20Hz, the power density is 1.0×106W/cm2, and the laser focus spot is 2mm below the liquid surface;During the laser irradiation process, the UV lamp is turned on at the same time, and the UV wavelength is 365nm.The light intensity is 10mW/cm2, and the irradiation time is 6h;At the same time of laser and ultraviolet irradiation, the microwave heating is turned on simultaneously, the microwave frequency is 2450MHz,Microwave power 800W, microwave time 6h,Control the heating temperature to 100, when the microwave reactor exceeds the predetermined temperature,The microwave generator will be turned off to cool down, and when the temperature is lower than the set temperature, the microwave generator will be turned on to heat up,Microwave heating should be accompanied by reflux condensation; after the reaction stops, the product is naturally cooled to room temperature,Introduce into a solution containing 200 mL of 10% sodium bisulfite, mechanically stir at a rate of 300r/min to remove remaining bromine, change the sodium bisulfite solution every 10 minutes, until the solution is colorless, stand still to separate the water layer , And then add 300mL methanol to the organic layer to produce granular precipitation. After centrifugal separation, the solid phase was washed with deionized water and absolute ethanol 3 times each.Dry at 80 for 48h to obtain brominated product; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
35% | With 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate In toluene at 140℃; for 48h; Inert atmosphere; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With tetrakis(triphenylphosphine) palladium(0) In toluene Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
55% | Stage #1: 1,8-dibromopyrene With n-butyllithium In tetrahydrofuran; hexane at 0℃; for 1h; Inert atmosphere; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran; hexane at 20℃; for 1h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: n-butyllithium / hexane; tetrahydrofuran / 1 h / 0 °C / Inert atmosphere 1.2: 1 h / 20 °C / Inert atmosphere 2.1: bromine / dichloromethane / 2 h / 40 °C 2.2: 1 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With bis-triphenylphosphine-palladium(II) chloride In N,N-dimethyl-formamide at 90℃; for 24h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
37.3% | With palladium diacetate; sodium carbonate In N,N-dimethyl-formamide at 110℃; for 4h; Glovebox; | 4 CompoundA 1.2 g (0.0033mol, 1eq), compound B2.16 g (0.00798 mol, 1.2eq) and Na2CO3 0.72 g (2eq) were added to a flask. Palladium (II) acetate 0.09 g (0.04eq) was added to glove box, DMF 70ml was added and reacted at 110 degrees C for 4 hours. The resulting mixture was extracted using chloroform and demineralized water and dried with MgSO4. The filtered liquid was washed with acetone and purified by column chromatography (MC:hexane = 1: 2) to yield 0.6 g of the compound represented by Formula 6a. The yield was 37.3%. |
With palladium diacetate; sodium carbonate In N,N-dimethyl-formamide at 110℃; for 4h; Glovebox; | 4 Flask compound A 1.2g (0.0033mol, 1eq), compound B 2.16g (0.00798 mol, 1.2eq) was added and the Na2CO3 0.72g (2eq). Then put the palladium (II) acetate, 0.09g (0.04eq) in the glove box, and then to put the semi-DMF 70ml were 4 hours at 110 . Then it extracted using chloroform with demineralized water and dried with MgSO4. With acetone and then filtered liquid was purified by column chromatography (MC: hexane = 1: 2) to yield 0.6g of the compound represented by the formula 6a. The yield was 37.3%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In toluene for 24h; Reflux; Inert atmosphere; | 1.1 1) Synthesis of 1,8-bis (4-tert-butylphenyl) pyrene (Compound Py18) Under nitrogen, 1,8-dibromopyrene (1.80 g, 5 mmol,4-tert-butylbenzeneboronic acid (2.14 g, 12 mmol)Tetrakis (triphenylphosphine) palladiumPd (PPh3) 4 (0.12 g, 0.1 mmol)And 2M potassium carbonate solution (12 mL) were dissolved in toluene (80 mL)Reflux for 24 hours.After completion of the reaction,The mixture was poured into water,The organic layer was extracted with dichloromethane and then dried over anhydrous MgSO4, The solvent was removed by steaming. The crude product was subjected to dry loading, using a mixture of n-hexane and methylene chloride as a eluent, And then using dichloromethane and ethanol (v: v = 1: 2)The mixture was recrystallized to give the pure compound Py18,White solid needle crystal.Yield: 1.7 g, 63%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In toluene Inert atmosphere; Reflux; | 1.3 3) Synthesis of 1,8-bis [4- (1- (4-tert-butylphenyl) -1H-benzimidazol-2-yl) -phenyl] pyrene (CompoundPyBM) Under a nitrogen atmosphere, 1,8-dibromopyrene (1.80 g, 5 mmol), 1-(4-tert-butylphenyl)-2-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]benzimidazole (5.44g, 12mmol), Pd(PPh3)4 (0.12 g , 0.1 mmol) and 2M potassium carbonate solution (12 mL) were dissolved in toluene (80 mL) and refluxed for 72 hours. After completion of the reaction, the mixture was poured into water, the organic layer was extracted with methylene chloride, then dried over anhydrous MgSO4 and the solvent was removed by rotary evaporation. The crude product was purified by dry loading, Using a mixture of n-hexane and ethyl acetate as the eluent to obtain a relatively pure compound PyBM by silica column. Finally, recrystallization from methylene chloride gave the pure compound PyBM as a white solid powder. Yield: 2.60 g, 61%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
58% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In toluene for 72h; Inert atmosphere; Reflux; | 4.3 3) Synthesis of 1,8-bis[4-(1-(4-phenyl)-1H-benzimidazol-2-yl)phenyl]pyrene (Compound PyBM1) Under nitrogen, 1,8-dibromopyrene (1.80g, 5mmol), 1-(4-phenyl)-2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]benzimidazole (4.75 g of, 12mmol), Pd (PPh3)4 (0.12 g of, 0.1 mmol), and 2M potassium carbonate solution (12 mL) was dissolved in toluene (80 mL) and refluxed for 72 hours. After the reaction, the mixture was poured into water, the organic layer was extracted with methylene chloride, then dried over anhydrous MgSO4, and the solvent was removed by rotary evaporation. The crude product was subjected to dry loading and a mixture of n-hexane and ethyl acetate was used as a eluent to obtain a pure compound PyBM1 as a white solid powder. Yield: 2.14 g, 58%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
56% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In toluene Inert atmosphere; Reflux; | 6.3 3) Synthesis of 1,8-bis[4-(1-(4-methoxyphenyl)-1H-benzimidazol-2-yl)phenyl]pyrene (Compound PyBM2) Under nitrogen, 1,8-dibromopyrene (1.80g, 5mmol), 1-(4-phenyl)-2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]benzimidazole (5.11 g, 12mmol), Pd(PPh3)4 (0.12 g of, 0.1 mmol), and 2M potassium carbonate solution (12 mL) was dissolved in toluene (80 mL) and refluxed for 72 hours. After the reaction, the mixture was poured into water, the organic layer was extracted with methylene chloride, then dried over anhydrous MgSO4, and the solvent was removed by rotary evaporation. The crude product was subjected to dry loading and a mixture of n-hexane and ethyl acetate was used as a eluent to obtain a pure compound PyBM2 as a white solid powder. Yield: 2.23 g, 56%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In toluene Inert atmosphere; Reflux; | 8.3 3) Synthesis of 1,8-bis[4-(1-(4-cyanophenyl)-1H-benzimidazol-2-yl)phenyl]pyrene (Compound PyBM3) Under a nitrogen atmosphere, 1,8-dibromopyrene (1.80 g, 5 mmol), 1-(4-cyanophenyl)-2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]benzimidazole (5.05g, 12mmol), Pd(PPh3)4 (0.12 g, 0.1 mmol) and 2M potassium carbonate solution (12 mL) was dissolved In toluene (80 mL) and refluxed for 72 hours. After the reaction, the mixture was poured into water, and the organic layer was extracted with methylene chloride, then dried over anhydrous MgSO4, and the solvent was removed by rotary evaporation. The crude product was subjected to dry loading and a mixture of n-hexane and ethyl acetate was used as a eluent to obtain a pure compound PyBM3 as a white solid powder. Yield: 1.97 g, 50%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With tri-tert-butyl phosphine; palladium diacetate; sodium t-butanolate In o-xylene at 125 - 130℃; for 3.5h; Inert atmosphere; | 1,8-Bis[N-(2-naphthyl)-N-phenylamino]pyrene 1 The mixture of 5.4 g(0.015 mol) of 1,8-dibromopyrene, 8.3 g (0.038 mol) of N-phenyl-N-(2-naphthyl)amine, 80 mg of palladium diacetate, 280 mg of tri(tert-butyl)phosphine,3.8 g (0.04 mol) of sodium tert-butoxide and 100 ml of o-xylenewas heated up to 125-130°C. The reaction mixture was stirred at thistemperature under argon atmosphere for 3.5 h. After cooling to roomtemperature the mixture was diluted with 100 ml of hexane. The solidproduct 1 was filtered, washed successively with hexane, methanol, waterand dried in vacuo over P2O5, yield 9.35 g (98%). 1H NMR, δ: 6.93-7.02(m, 2 H), 7.05 (d, 3H, J 7.9 Hz), 7.08-7.11 (m, 1H), 7.13 (d, 1H, J 7.5 Hz), 7.17 and 7.19 (2d, 3H, J 7.9 Hz), 7.23 (d, 1H, J 7.4 Hz), 7.26-7.37 (m,7H), 7.44 (d, 1H, J 7.9 Hz), 7.48 (d, 1H, J 7.6 Hz), 7.64 (d, 1H, J 8.7 Hz),7.68-7.75 (m, 3H), 7.83 (d, 1H, J 8.2 Hz), 7.84 (d, 1H, J 8.1 Hz), 7.90(d, 1H, J 9.2 Hz), 8.03 (s, 1H), 8.05 (s, 1H), 8.10 (d, 1H, J 8.1 Hz), 8.17(d, 2H, J 8.3 Hz). IR (ν/cm-1): 3057, 1630, 1593 (C=C), 1574, 1508,1491, 1467, 1421, 1388, 1362, 1294, 1273, 1237, 1184, 1077, 972, 939,874, 846, 816, 747, 696. MS, m/z: 636 [M]+. Found (%): C, 90.41; H, 5.31;N, 3.97. Calc. for C48H32N2 (%): C, 90.53; H, 5.07; N, 4.40. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With tri-tert-butyl phosphine; palladium diacetate; sodium t-butanolate In o-xylene at 125 - 130℃; for 3h; Inert atmosphere; | 1,8-Bis[N,N-bis(4-tert-butylphenyl)amino]pyrene 2 The mixture of 5.4 g(0.015 mol) of 1,8-dibromopyrene, 10.54 g (0.038 mol) of bis(4-tert-butylphenyl)amine, 80 mg of palladium diacetate, 280 mg of tri(tert-butyl)phosphine,3.8 g (0.04 mol) of sodium tert-butoxide and 100 ml of o-xylenewas heated up to 125-130°C. The reaction mixture was stirred at thistemperature under argon atmosphere for 3 h. After cooling to room temperaturethe mixture was diluted with 100 ml of benzene and filteredfrom the precipitate, which was washed on the filter with 50 ml ofbenzene. The combined filtrates were evaporated to dryness and 50 ml ofmethanol was added to the residue. A precipitate thus formed was filtered,air dried, and recrystallized from a benzene-hexane mixture. Yield 11.14 g(98%). 1H NMR, δ: 1.26 (s, 36 H, 4-But), 6.90-6.98 (m, 8 H), 7.14-7.19(m, 8 H), 7.81 (d, 2H, J 8.1 Hz), 7.98-8.20 (m, 6 H). IR (ν/cm-1): 3034,2961 (CH, But), 1599, 1509 (C=C), 1493, 1459, 1423, 1393, 1363, 1337,1321, 1302, 1268, 1189, 1121, 1024, 1014, 928, 849, 826, 735, 723, 698.MS, m/z: 761 [M]+. Found (%): C, 87.91; H, 7.79; N, 3.99. Calc. forC56H60N2 (%): C, 88.37; H, 7.95; N, 3.68. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
40% | With tri-tert-butyl phosphine; palladium diacetate; sodium t-butanolate In o-xylene at 125 - 130℃; for 3.5h; Inert atmosphere; | 1,8-Bis[N-(1-naphthyl)-N-phenylamino]pyrene 3 The mixture of 5.4 g(0.015 mol) of 1,8-dibromopyrene, 8.3 g (0.038 mol) of N-phenyl-N-(1-naphthyl)amine, 80 mg of palladium diacetate, 280 mg of tri(tert-butyl)phosphine,3.8 g (0.04 mol) of sodium tert-butoxide and 100 ml of o-xylenewas heated up to 125-130°C. The reaction mixture was stirred at thistemperature under argon atmosphere for 3.5 h. After cooling to roomtemperature, the mixture was diluted with 100 ml of hexane and filteredfrom the precipitate (5.4 g, by-products), the filtrate was evaporated todryness. The residue was treated with 30 ml of acetone and then 30 ml ofmethanol was added to the mixture. Yellow precipitate was filtered, washedwith methanol, dried in vacuo over P2O5. Yield 3.81 g (40%). 1H NMR,δ: 6.70 (d, 4H, J 7.9 Hz), 6.84 and 6.85 (2 d, 2H, J 7.3 Hz), 7.08 and 7.09(2 d, 4H, J 7.9 Hz), 7.21 (d, 2H, J 6.9 Hz), 7.27-7.35 (m, 4H), 7.42 and7.44 (2 d, 2H, J 7.1 Hz), 7.68 (d, 2H, J 8.2 Hz), 7.74 (d, 2H, J 8.2 Hz),7.86 (d, 2H, J 8.1 Hz), 7.95 (s, 2 H), 8.02-8.08 (m, 4 H), 8.11 (s, 2H). IR (ν/cm-1): 3042, 1594 (C=C), 1574, 1504, 1490, 1460, 1421, 1393,1334, 1274, 1247, 1214, 1185, 1136, 1076, 1020, 968, 865, 850, 828,817, 798, 791, 774, 735, 696. MS, m/z: 636 [M]+. Found (%): C, 89.69;H, 5.26; N, 4.47. Calc. for C48H32N2 (%): C, 90.53; H, 5.07; N, 4.40. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | With palladium diacetate; tetraethylammonium hydroxide; tricyclohexylphosphine In tetrahydrofuran; toluene at 50 - 80℃; for 2h; Inert atmosphere; | 1,8-DTBP. Compound 6 (1.00 g, 2.78 mmol), compound 4 (2.63 g,6.08 mmol), Pd(OAc)2 (0.06 g, 0.28 mmol), and (cyclohexyl)3P (0.12 g,0.42 mmol) were added to 30 mL of anhydrous THF and 170 mL ofanhydrous toluene mixture. Then tetraethylammonium hydroxide(20 wt%) (35 mL) was added to the reaction mixture at 50 °C. Themixture was heated to 80 °C for 2 h under nitrogen. After the reactionwas finished, the reaction mixture was extracted with CHCl3 and water.The organic layer was dried with anhydrous MgSO4 and filtered. Thesolvent was evaporated. The product was isolated by silica gel columnchromatography using the CHCl3: n-hexane (1: 10) eluent to afford abeige solid (1.51 g, 67%). 1H NMR (300 MHz, [D8]THF): δ=8.35 (d,2H), 8.29 (s, 2H), 8.20 (s, 2H), 8.11 (d, 2H), 8.03 (m, 8H), 7.92 (s, 2H),7.83 (m, 12H), 7.50 (t, 8H), 7.39 (t, 4H); 13C NMR (125 MHz, CDCl3):δ=142.63, 142.10, 141.31, 140.58, 140.20, 137.30, 131.28, 131.20,129.04, 128.57, 127.89, 127.75, 127.69, 127.54, 127.48, 125.63,125.48, 125.33, 125.10; HRMS (EI, m/z): [M+] calcd for C64H42,810.3287; found, 810.3291; elemental analysis calcd (%) for C64H42: C94.78, H 5.22; found: C 94.39, H 5.31%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 28% 2: 16% | With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; triphenylphosphine Inert atmosphere; Reflux; | 2.2.3. Synthesis of 9-(2-ethylhexyl)-7-(pyren-1-ylethynyl)-9H-carbazole-2-carbonitrile (5a) General procedure: A mixture of 1-bromopyrene (0.5 g, 1.78 mmol), 9-(2-ethylhexyl)-7-ethynyl-9H-carbazole-2-carbonitrile (0.59 g, 1.78 mmol), Pd(PPh3)2Cl2(12.5 mg, 0.018 mmol), PPh3 (9.4 mg, 0.036 mmol), CuI (3.5 mg,0.018 mmol), triethylamine (30 mL) was mixed under nitrogen atmosphere.The resulting mixture was refluxed for 12 h under nitrogen atmosphere.After completion of the reaction, the mixture was pouredinto water and extracted with chloroform. The organic layer was driedover sodium sulfate. Finally, the solvent was removed under vacuum toyield a residue which was purified by column chromatography usinghexane/chloroform (4:1) as eluent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: hydrogenchloride; sulfuric acid / water / 0.17 h / Reflux 1.2: 3 h / 5 - 60 °C 2.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -85 °C / Inert atmosphere 2.2: 20 °C / Inert atmosphere 3.1: sodium t-butanolate / tetrahydrofuran / 0.5 h / 5 °C 3.2: Wittig Olefination / 2 h / 5 - 30 °C 4.1: methanesulfonic acid / dichloromethane / 1 h / -10 - 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -85 °C / Inert atmosphere 1.2: 20 °C / Inert atmosphere 2.1: sodium t-butanolate / tetrahydrofuran / 0.5 h / 5 °C 2.2: Wittig Olefination / 2 h / 5 - 30 °C 3.1: methanesulfonic acid / dichloromethane / 1 h / -10 - 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83.6% | With methanesulfonic acid In dichloromethane at -10 - 20℃; for 1h; Inert atmosphere; | 1.5 (5) Cyclization reaction 500 ml three-neck bottle,Nitrogen protection,5.08 g (0.01 mol) of the compound of the formula A-1 is added, 100 ml of dichloromethane, cooling to 0 ~ -10 ° C,5.8 g (0.06 mol) of methanesulfonic acid was added dropwise at 0 to -10 °C.Slowly warm up to 20 ° C,Stay for 1 hour,Obtaining a reaction liquid containing 1,8-dibromoindole represented by the formula (1),The reaction solution containing 1,8-dibromoindole represented by the formula (1) is filtered,Obtaining crude 1,8-dibromoindole,Wash the crude product,Wash with methanol,2.99 g of 1,8-dibromoindole was obtained in a yield of 83.06%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75.3% | With methanesulfonic acid In dichloromethane at -10 - 20℃; for 1h; Inert atmosphere; | 2.6 (6) cyclization reaction 500 ml three-neck bottle,Nitrogen protection,4.24 g (0.01 mol) of the compound of the formula A-2 is added,100 ml of dichloromethane,Cool down to 0 ~ -10 ° C,5.8 g (0.06 mol) of methanesulfonic acid was added dropwise at 0 to -10 °C.Slowly warm up to 20 ° C,Stay for 1 hour,Obtaining a reaction liquid containing 1,8-dibromoindole represented by the formula (1),The reaction solution containing 1,8-dibromoindole represented by the formula (1) is filtered,Obtaining crude 1,8-dibromoindole,Wash the crude product,Wash with methanol,Obtained 2.71 g of 1,8-dibromofluorene,The yield was 75.3%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With methanesulfonic acid In dichloromethane at -10 - 20℃; for 1h; Inert atmosphere; | 3 (5) Cyclization reaction 500 ml three-neck bottle,Nitrogen protection,5.08 g (0.01 mol) of the compound of the formula A-1 is added, 100 ml of dichloromethane, cooling to 0 ~ -10 ° C,5.8 g (0.06 mol) of methanesulfonic acid was added dropwise at 0 to -10 °C.Slowly warm up to 20 ° C,Stay for 1 hour,Obtaining a reaction liquid containing 1,8-dibromoindole represented by the formula (1),The reaction solution containing 1,8-dibromoindole represented by the formula (1) is filtered,Obtaining crude 1,8-dibromoindole,Wash the crude product,Wash with methanol,2.99 g of 1,8-dibromoindole was obtained in a yield of 83.06%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With methanesulfonic acid In dichloromethane at -10 - 20℃; for 1h; Inert atmosphere; | 4 (5) Cyclization reaction 500 ml three-neck bottle,Nitrogen protection,5.08 g (0.01 mol) of the compound of the formula A-1 is added, 100 ml of dichloromethane, cooling to 0 ~ -10 ° C,5.8 g (0.06 mol) of methanesulfonic acid was added dropwise at 0 to -10 °C.Slowly warm up to 20 ° C,Stay for 1 hour,Obtaining a reaction liquid containing 1,8-dibromoindole represented by the formula (1),The reaction solution containing 1,8-dibromoindole represented by the formula (1) is filtered,Obtaining crude 1,8-dibromoindole,Wash the crude product,Wash with methanol,2.99 g of 1,8-dibromoindole was obtained in a yield of 83.06%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: 5%-palladium/activated carbon; hydrogen / ethanol / 40 °C / 2250.23 Torr / Autoclave 2.1: hydrogenchloride; sulfuric acid / water / 0.17 h / Reflux 2.2: 3 h / 5 - 60 °C 3.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -85 °C / Inert atmosphere 3.2: 20 °C / Inert atmosphere 4.1: sodium t-butanolate / tetrahydrofuran / 0.5 h / 5 °C 4.2: Wittig Olefination / 2 h / 5 - 30 °C 5.1: methanesulfonic acid / dichloromethane / 1 h / -10 - 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | With bis-triphenylphosphine-palladium(II) chloride In tetrahydrofuran at 80℃; Inert atmosphere; Schlenk technique; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
40% | With bis-triphenylphosphine-palladium(II) chloride In tetrahydrofuran at 80℃; Inert atmosphere; Schlenk technique; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: sodium carbonate; tetrakis(triphenylphosphine) palladium(0) / ethanol; toluene; water / 5 h / Inert atmosphere; Reflux 2: triethyl phosphite / 1,2-dichloro-benzene / 15 h / 150 °C 3: potassium <i>tert</i>-butylate; tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine / 5,5-dimethyl-1,3-cyclohexadiene / 6 h / Reflux 4: potassium <i>tert</i>-butylate; tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine / 5,5-dimethyl-1,3-cyclohexadiene / 6 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: sodium carbonate; tetrakis(triphenylphosphine) palladium(0) / ethanol; toluene; water / 5 h / Inert atmosphere; Reflux 2: triethyl phosphite / 1,2-dichloro-benzene / 15 h / 150 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: sodium carbonate; tetrakis(triphenylphosphine) palladium(0) / ethanol; toluene; water / 5 h / Inert atmosphere; Reflux 2: triethyl phosphite / 1,2-dichloro-benzene / 15 h / 150 °C 3: potassium <i>tert</i>-butylate; tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine / 5,5-dimethyl-1,3-cyclohexadiene / 6 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: sodium carbonate; tetrakis(triphenylphosphine) palladium(0) / ethanol; toluene; water / 5 h / Inert atmosphere; Reflux 2: triethyl phosphite / 1,2-dichloro-benzene / 15 h / 150 °C 3: potassium <i>tert</i>-butylate; tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine / 5,5-dimethyl-1,3-cyclohexadiene / 6 h / Reflux 4: potassium <i>tert</i>-butylate; tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine / 5,5-dimethyl-1,3-cyclohexadiene / 6 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene for 5h; Inert atmosphere; Reflux; | 1.1; 2.1 Example 1: Preparation of Compound 1 Step1. Take 1-4 100mmol, add 2 equivalents of o-nitrophenylboronic acid,Sodium carbonate 300mmol, tetrakistriphenylphosphine palladium 1mmol, toluene,A mixed solvent of ethanol and water, substituted three times with argon, and reacted at reflux temperature for 5 hours.After the reaction is completed, deionized water is added, the organic phase is separated, and washed three times with water.Concentrated, the crude product obtained is passed through a silica gel column.The product was obtained 1-3 80 mmol. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: copper(l) iodide; triphenylphosphine; triethylamine; bis-triphenylphosphine-palladium(II) chloride / triethylamine / Inert atmosphere; Reflux 2: tetrabutyl ammonium fluoride; copper(l) iodide; triphenylphosphine; bis-triphenylphosphine-palladium(II) chloride / triethylamine; tetrahydrofuran / Inert atmosphere; Reflux 3: acetonitrile / UV-irradiation |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: copper(l) iodide; triphenylphosphine; triethylamine; bis-triphenylphosphine-palladium(II) chloride / triethylamine / Inert atmosphere; Reflux 2: tetrabutyl ammonium fluoride; copper(l) iodide; triphenylphosphine; bis-triphenylphosphine-palladium(II) chloride / triethylamine; tetrahydrofuran / Inert atmosphere; Reflux 3: acetonitrile / UV-irradiation |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: copper(l) iodide; triphenylphosphine; triethylamine; bis-triphenylphosphine-palladium(II) chloride / triethylamine / Inert atmosphere; Reflux 2: tetrabutyl ammonium fluoride; copper(l) iodide; triphenylphosphine; bis-triphenylphosphine-palladium(II) chloride / triethylamine; tetrahydrofuran / Inert atmosphere; Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: copper(l) iodide; triphenylphosphine; triethylamine; bis-triphenylphosphine-palladium(II) chloride / triethylamine / Inert atmosphere; Reflux 2: tetrabutyl ammonium fluoride; copper(l) iodide; triphenylphosphine; bis-triphenylphosphine-palladium(II) chloride / triethylamine; tetrahydrofuran / Inert atmosphere; Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine at 90℃; for 16h; | ||
Stage #1: 1,8-dibromopyrene; trimethylsilylacetylene With diisopropylamine In tetrahydrofuran at 100℃; Inert atmosphere; Microwave irradiation; UV-irradiation; Stage #2: With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide In tetrahydrofuran for 4h; Reflux; Inert atmosphere; | 1.B; 2.B; 3.B; 4.B; 5.B; 6.B; 7.B; 8B; 9.B; 10.B; 11.B; 12.B; 13.B; 14.B B. Sonogashira coupling reaction: Dissolve the 5mmol product obtained in A in a mixed solution of 30mL tetrahydrofuran and 30mL diisopropylamine, place it in a 100mL two-necked flask, pass argon protection at a rate of 1L/min, and then add 25mmol terminal alkynyl trimethylsilyl.Move the 100mL three-necked flask into a microwave reactor with laser and ultraviolet irradiation at atmospheric pressure and reflux device, turn on the reflux condenser,Then irradiate the solution with a Nd:YAG solid-state pulsed laser, where the laser parameters are wavelength 1.06μm, pulse width 1.2ms, spot diameter 0.2mm, repetition frequency 20Hz, power density 1.0×106W/cm2, and laser focus spot is 2mm below the liquid surface ; During the laser irradiation process, turn on the ultraviolet light at the same time, the ultraviolet wavelength is 365nm, the light intensity is 10mW/cm2; while the laser and ultraviolet irradiation, the microwave heating is turned on simultaneously, the microwave frequency is 2450MHz, the microwave power is 650W, and the system is heated to 100 , when the temperature in the microwave reactor exceeds the predetermined temperature, the microwave generator will be turned off to cool down. When the temperature is lower than the predetermined temperature, the microwave generator will be turned on to increase the temperature, adding 0.2mmol of triphenylphosphorus palladium dichloride and 0.2mmol of cuprous iodide. Argon protection at a rate of 1L/min, reflux reaction for 4h, after stopping the reaction, rotary steam at -0.09MPa, temperature 60°C, and a rate of 90r/min for 30min to remove the solvent and pass through the column. The developing solvent is n-hexane and dichloride by volume. Methane 1:1 mixed solvent,Get product |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / toluene / 24 h / 90 °C 2: tetrakis(triphenylphosphine) palladium(0); potassium phosphate tribasic trihydrate / water; 1,2-dimethoxyethane / 48 h / 105 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / toluene / 24 h / 90 °C 2: tetrakis(triphenylphosphine) palladium(0); potassium phosphate tribasic trihydrate / water; 1,2-dimethoxyethane / 48 h / 105 °C 3: bromine / dichloromethane / 2 h / 40 °C 4: tetrakis(triphenylphosphine) palladium(0); copper(l) iodide; triethylamine; 1,8-diazabicyclo[5.4.0]undec-7-ene / 16 h / 90 °C 5: potassium fluoride; copper(ll) sulfate pentahydrate; sodium L-ascorbate; pyridine / ethanol; water / 24 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / toluene / 24 h / 90 °C 2: tetrakis(triphenylphosphine) palladium(0); potassium phosphate tribasic trihydrate / water; 1,2-dimethoxyethane / 48 h / 105 °C 3: bromine / dichloromethane / 2 h / 40 °C 4: tetrakis(triphenylphosphine) palladium(0); copper(l) iodide; triethylamine; 1,8-diazabicyclo[5.4.0]undec-7-ene / 16 h / 90 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / toluene / 24 h / 90 °C 2: tetrakis(triphenylphosphine) palladium(0); potassium phosphate tribasic trihydrate / water; 1,2-dimethoxyethane / 48 h / 105 °C 3: bromine / dichloromethane / 2 h / 40 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium(0); copper(l) iodide; triethylamine / 16 h / 90 °C 2: potassium fluoride; copper(ll) sulfate pentahydrate; sodium L-ascorbate; pyridine / ethanol; water / 24 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In toluene at 90℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane 2: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane / 96 h / 100 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane 2.1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane / 96 h / 100 °C 3.1: hydrogen bromide / water / 3 h / 20 °C 3.2: Aliquat / 14 h / 130 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With copper(l) iodide; caesium carbonate In N,N-dimethyl-formamide at 120℃; for 40h; Schlenk technique; Inert atmosphere; | Procedure for synthesis 1-3: General procedure: In 25 mL Schlenk flask, di- ortetrabromopyrene (1.0 mmol), pyrazole (2.8/5.6 mmol), cesiumcarbonate (4.0/8.0 mmol), copper(I) iodide (0.4/0.8 mmol) wereplaced. The flaskwas three times evacuated and refilled with argon,subsequently dry DMF (6 mL) was added by syringe. The mixturewas stirring and heating for 24 h/40 h at 120° C. After the reactionwas completed, the mixture was cooled to room temperature andfiltrated by G3 fritted funnel and washed with hexane and diethylether. The products were obtained as grey solids.1 (0.314 g, 94% yield) . |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | Stage #1: pyrene With hydrogen bromide; dihydrogen peroxide In methanol; diethyl ether; water at 20℃; for 24h; Inert atmosphere; Stage #2: With bromine In nitrobenzene at 20℃; for 12h; Inert atmosphere; Overall yield = 74 percent; Overall yield = 8 g; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: diisopropylamine / tetrahydrofuran / 100 °C / 760.05 Torr / Inert atmosphere; Microwave irradiation; UV-irradiation 1.2: 4 h / Reflux; Inert atmosphere 2.1: bromine / nitrobenzene / 20 h / 110 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: diisopropylamine / tetrahydrofuran / 100 °C / 760.05 Torr / Inert atmosphere; Microwave irradiation; UV-irradiation 1.2: 4 h / Reflux; Inert atmosphere 2.1: bromine / nitrobenzene / 20 h / 110 °C 3.1: potassium carbonate; methanol / tetrahydrofuran / 6 h / 20 °C / Flow reactor |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: diisopropylamine / tetrahydrofuran / 100 °C / 760.05 Torr / Inert atmosphere; Microwave irradiation; UV-irradiation 1.2: 4 h / Reflux; Inert atmosphere 2.1: bromine / nitrobenzene / 20 h / 110 °C 3.1: potassium carbonate; methanol / tetrahydrofuran / 6 h / 20 °C / Flow reactor 4.1: copper(l) iodide / N,N-dimethyl-formamide / 4 h / 100 °C / 760.05 Torr / Inert atmosphere; Microwave irradiation; UV-irradiation |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: diisopropylamine / tetrahydrofuran / 100 °C / 760.05 Torr / Inert atmosphere; Microwave irradiation; UV-irradiation 1.2: 4 h / Reflux; Inert atmosphere 2.1: bromine / nitrobenzene / 20 h / 110 °C 3.1: potassium carbonate; methanol / tetrahydrofuran / 6 h / 20 °C / Flow reactor 4.1: copper(l) iodide / N,N-dimethyl-formamide / 4 h / 100 °C / 760.05 Torr / Inert atmosphere; Microwave irradiation; UV-irradiation 5.1: diisopropylamine / tetrahydrofuran / 120 °C / 760.05 Torr / Inert atmosphere; UV-irradiation; Microwave irradiation 5.2: 4 h / Inert atmosphere; Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: diisopropylamine / tetrahydrofuran / 100 °C / 760.05 Torr / Inert atmosphere; Microwave irradiation; UV-irradiation 1.2: 4 h / Reflux; Inert atmosphere 2.1: bromine / nitrobenzene / 20 h / 110 °C 3.1: potassium carbonate; methanol / tetrahydrofuran / 6 h / 20 °C / Flow reactor 4.1: copper(l) iodide / N,N-dimethyl-formamide / 4 h / 100 °C / 760.05 Torr / Inert atmosphere; Microwave irradiation; UV-irradiation 5.1: diisopropylamine / tetrahydrofuran / 120 °C / 760.05 Torr / Inert atmosphere; UV-irradiation; Microwave irradiation 5.2: 4 h / Inert atmosphere; Reflux 6.1: potassium carbonate; methanol / tetrahydrofuran / 6 h / 20 °C / Flow reactor |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In tetrahydrofuran for 24h; Reflux; Inert atmosphere; | 2.3. Synthesis and characterization General procedure: A mixture of dibromoanthracenes/dibromopyrenes 3, 4, 5, 6, 7 or 8(0.30 mmol), dioxaborolane 2 (0.71 mmol), Pd(PPh3)4 (0.01 mmol) and2 M Na2CO3 (10 ml) in THF (30 ml) was degassed with N2 for 5 min andthen heated at refilux under N2 atmosphere for 24 h. After cooling toroom temperature, the mixture was extracted with DCM (50 ml x 2) andthe combined organic phase was washed with water (50 ml) and brinesolution (50 ml), dried over anhydrous Na2SO4, filtered and removed thesolvent to dryness. The crude product was purified using silica gel columnchromatography eluting with 20% DCM:hexane followed byrecrystallization in DCM/MeOH mixture. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With copper (I) iodide; tetrakis-(triphenylphosphine)-palladium; di-i-propyl amine In toluene at 40℃; for 48h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With copper (I) iodide; tetrakis-(triphenylphosphine)-palladium; di-i-propyl amine In toluene at 40℃; for 48h; Inert atmosphere; |
Tags: 38303-35-4 synthesis path| 38303-35-4 SDS| 38303-35-4 COA| 38303-35-4 purity| 38303-35-4 application| 38303-35-4 NMR| 38303-35-4 COA| 38303-35-4 structure
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