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Chemical Structure| 94928-86-6
Chemical Structure| 94928-86-6
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Product Details of [ 94928-86-6 ]

CAS No. :94928-86-6 MDL No. :MFCD12022527
Formula : C33H24IrN3 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 654.78 Pubchem ID :-
Synonyms :

Calculated chemistry of [ 94928-86-6 ]

Physicochemical Properties

Num. heavy atoms : 37
Num. arom. heavy atoms : 36
Fraction Csp3 : 0.0
Num. rotatable bonds : 3
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 149.02
TPSA : 38.67 Ų

Pharmacokinetics

GI absorption : Low
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -4.87 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 7.66
Log Po/w (WLOGP) : 8.25
Log Po/w (MLOGP) : 4.36
Log Po/w (SILICOS-IT) : 3.09
Consensus Log Po/w : 4.67

Druglikeness

Lipinski : 2.0
Ghose : None
Veber : 0.0
Egan : 1.0
Muegge : 2.0
Bioavailability Score : 0.17

Water Solubility

Log S (ESOL) : -9.27
Solubility : 0.000000356 mg/ml ; 0.0000000005 mol/l
Class : Poorly soluble
Log S (Ali) : -8.31
Solubility : 0.00000321 mg/ml ; 0.0000000049 mol/l
Class : Poorly soluble
Log S (SILICOS-IT) : -4.53
Solubility : 0.0196 mg/ml ; 0.0000298 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 3.08

Safety of [ 94928-86-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 94928-86-6 ]

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

  • Upstream synthesis route of [ 94928-86-6 ]
  • Downstream synthetic route of [ 94928-86-6 ]

[ 94928-86-6 ] Synthesis Path-Upstream   1~15

  • 1
  • [ 1008-89-5 ]
  • [ 94928-86-6 ]
YieldReaction ConditionsOperation in experiment
90.4% at 198 - 200℃; for 1.1 h; Microwave irradiation; Inert atmosphere 300 g of 2-phenylpyridinato, 30.1 g of a chlorine-bridged iridium dimer (D-1) and 3 L of special-grade ethylene glycol were placed in a 6 L separable flask, and the flask was set in a cavity-type microwave irradiation apparatus (SMW-124 manufactured by Shikoku Instrumentation CO., Inc.). An argon gas was blown into the reaction solution for 30 minutes, the reaction solution was thereafter irradiated with a microwave (2450 MHz) at 6 kW while the reaction solution was magnetically stirred, the temperature was elevated from room temperature to a boiling state (around 198° C. to 200° C.) in about 6 minutes, and the reaction solution was further irradiated with a microwave at 6 kW for an hour under an argon atmosphere, and reacted at around 198° C. to 200° C. The reaction solution was cooled to room temperature, and thereafter the reaction solution was filtered to obtain a yellow solid. The yellow solid was washed with methanol, pure water and methanol again, thereafter dried in a vacuum, and recrystallized from a mixed solvent of DMF and methanol to obtain a complex of tris-orthometallated iridium (T-1) described in chemical formula (chemical formula 11) (yield amount: 33.5 g; yield: 90.4percent). The product was analyzed by HPLC (Prominence manufactured by Shimadzu Corporation; detected wavelength: 300 nm), and resultantly found to be a mixture of a facial isomer and a meridional isomer at a ratio of 99.2:0.8 (molar ratio).
85.9%
Stage #1: With silver trifluoromethanesulfonate In 2-ethoxy-ethanol at 20℃; for 0.166667 h;
Stage #2: for 3 h; Heating / reflux
In a Schlenk's flask equipped with a reflux condenser was placed (1,5-cyclooctadiene)iridium(I) chloride dimer (500 mg, 0. 744 mmol, 1 equivalent) and the interior of the flask was substituted with nitrogen. There were successively added 2-ethoxyethanol (5 mL, s/s=10) and 2-phenylpyridine (468 μL, 3.274 mmol, 4.4 equivalents), and the mixture was stirred in a nitrogen atmosphere under refluxing (135°C) for 3 hours. The resulting yellow suspension was cooled to room temperature, to which was added silver (I) trifluoromethanesulfonate (573 mg, 2.232 mmol, 3.0 equivalents), and further stirred at room temperature for 10 minutes to give a dark brown suspension. There was added an additional amount of 2-ethoxyethanol (7 mL, s/s=14) and then dropwise added 2-phenylpyridine (638 μL, 4.464 mmol, 6.0 equivalents), and the mixture was further stirred under refluxing for 3 hours to give an ocher suspension. The solvent was distilled off from the reaction mixture under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: dichloromethane). The column fractions were condensed, and the resulting yellow solid was recrystallized from hexane/dichloromethane to give 837 mg of the title compound (V-i) as yellow powder in 85.9percent yield. 1H NMR (500MHz CD2Cl2) : δ 6.72-6.81 (m, 6H), 6.85-6.93 (m, 6H), 7.56 (ddd, J=0.8, 1.6, 5.5Hz, 3H), 7.62-7.69 (m, 6H), 7.89-7.94 (m, 3H).
83.4% With silver trifluoromethanesulfonate In 2-ethoxy-ethanol at 135℃; for 3 h; Heating / reflux In a Schlenk's flask were placed Compound (II-i) (Bis(2-phenylpyridinato-N,C2')iridium(III) chloride dimer) produced in Example 1 (200 mg, 0.187 mmol, 1 equivalent) and silver(I) trifluoromethanesulfonate (144 mg, 0. 561 mmol, 3.0 equivalents), and the interior of the flask was substituted with nitrogen. There were added 2-ethoxyethanol (1 ml, s/s=5) and 2-phenylpyridine (163 μL, 1.122 mmol, 6.0 equivalents), and the mixture was stirred under refluxing (135°C) for 3 hours. The resulting ocher suspension was condensed, and the residue was purified by silica gel column chromatography (eluent: dichloromethane). The column fractions were condensed, and recrystallized from hexane/dichloromethane to give 208 mg of the title compound (V-i) as yellow powder in 83.4percent yield. NMR data of the product was identical to that of Example 11.
78%
Stage #1: With sodium carbonate In monoethylene glycol diethyl etherReflux; Industry scale
Step Two:Added 1200 ml of Ethylene Glycol ether to 3 L of four-neck flask, followed with 18 g of Chlorendic compounds, stirred, Nitrogen gas filled in, then heated and refluxed. When the reflux occurred in the flask, added 12 g of solid sodium carbonate all at once. Dissolved 2-Phenyl Pyridine in 100 ml of Glycerol, and then dripped the mixture in forty minutes by using constant pressure drop funnel. Refluxed with stirring, with sampling interval 1 hour, and 2-3 hours later terminated the reaction. (HPLC: products 95percent-97percent)Cooled the reaction system, added 5.5 L of ethyl acetate, and then rinsed with 4 L.x.3 DI water. Dried the organic phase and concentrated solvent with 200 g of Magnesium Sulfate, and deep yellow solid substances reached. By using Methyl Cyanide, the deep yellow solid substances were recrystallized and 15 g of luminous yellow solid substances with 78percent of yield rate reached.1H-NMR (CDCl3, 400Hz): 7.84 (m, 3H), 7.58 (m, 6H), 7.48 (m, 3H), 6.83 (m, 6H), 6.69 (m, 6H).

Reference: [1] Patent: US2013/203997, 2013, A1, . Location in patent: Paragraph 0100
[2] Patent: WO2004/43974, 2004, A1, . Location in patent: Page/Page column 68-69
[3] Patent: WO2004/43974, 2004, A1, . Location in patent: Page/Page column 72
[4] Patent: US2012/309971, 2012, A1, . Location in patent: Page/Page column 4-5
[5] Angewandte Chemie - International Edition, 2016, vol. 55, # 5, p. 1872 - 1875[6] Angew. Chem., 2016, vol. 128, # 5, p. 1904 - 1907,4
  • 2
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YieldReaction ConditionsOperation in experiment
87% With sodium acetylacetonate In ethylene glycol at 180℃; for 17 h; Inert atmosphere 167.0 mg (0.3 mmol) of iridium compound (Ir - 2), 162.7 mg (1.05 mmol) of ligand (L - 1), 44 sodium acetylacetonate hydrate as β - diketonate salt, 0 mg (0.36 mmol), and ethylene glycol (2.5 ml) were placed in a three-necked flask and reacted under heating in an argon atmosphere at 180 ° C. for 17 hours. After completion of the reaction, the reaction solution was cooled to room temperature, and the precipitated yellow solid was washed with methanol. From the analysis result of 1 H-NMR, the precipitated yellow solid was the desired iridium complex (T-1), and the yield was 87percent.
Reference: [1] Patent: JP2017/226634, 2017, A, . Location in patent: Paragraph 0086
  • 3
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YieldReaction ConditionsOperation in experiment
80% With sodium acetylacetonate In ethylene glycol at 180℃; for 17 h; Inert atmosphere 145.3 mg (0.3 mmol) of iridium compound (Ir - 1), 279.0 mg (1.8 mmol) of ligand (L - 1), sodium acetylacetonate hydrate as a β - diketonate salt, 6 mg (0.75 mmol), and ethylene glycol 2.5 ml were placed in a three-necked flask and reacted under heating in an argon atmosphere at 180 ° C. for 17 hours. After completion of the reaction, the reaction solution was cooled to room temperature, and the precipitated yellow solid was washed with methanol. From the analysis result of 1 H-NMR, the yellow solid precipitated was the desired iridium complex (T-1), and the yield was 80percent.
Reference: [1] Patent: JP2017/226634, 2017, A, . Location in patent: Paragraph 0084
  • 4
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YieldReaction ConditionsOperation in experiment
92% With phosphoric acid In water; glycerol at 200 - 210℃; for 10 h; Heating / reflux In a three-necked flask equipped with a reflux condenser was placed 100 ml of glycerin and the flask was swept free of air by blowing N2 for 3.5 hours. Thereafter, 2.0 g of iridium(III) acetylacetonate, 7.5 g of 2-phenylpyridine, and 5.9 g of phosphoric acid (85percent aqueous solution) were added and, in a nitrogen atmosphere, the mixture was heated under reflux in an oil bath at a bath temperature of 200-210°C with stirring for 10 hours. Upon completion of the reaction, the mixture was cooled to room temperature, 30 ml of ethanol and 300 ml of 2N HCl were added, the mixture was stirred, and the precipitate was filtered. The precipitate was transferred to a beaker, washed with 50 ml of ethanol with stirring, and filtered again. The precipitate thus obtained was transferred to a 100-ml eggplant-shaped flask, 60 ml of acetonitrile was added, and the mixture was heated in an oil bath at a bath temperature of 100°C for 1 hour. The mixture was cooled to room temperature and the precipitate was filtered, washed with 30 ml of acetonitrile and 30 ml of ethanol, and dried under reduced pressure at 80°C for 5 hours to give 2.4 g of yellow crystals. An MS analysis identified the yellow crystal as ortho-metalated iridium complex (2): yield, 92percent; purity by HPLC, 99percent; MS (ESI-TOFMS), 655.
68% With tartaric acid In glycerol at 200 - 210℃; for 5 - 44 h; Heating / reflux In a three-necked flask equipped with a reflux condenser was placed 100 ml of glycerin and the flask was swept free of air by blowing N2 for 3.5 hours. Thereafter, 2.0 g of iridium(III) acetylacetonate, 7.5 g of 2-phenylpyridine, and 3.3 g of tartaric acid were added and, in a nitrogen atmosphere, the mixture was heated under reflux in an oil bath at a bath temperature of 200-210°C with stirring for 10 hours. Upon completion of the reaction, the mixture was cooled to room temperature, 30 ml of ethanol and 300 ml of 2N HCl were added, the mixture was stirred, and the precipitate was filtered. The precipitate was transferred to a beaker, washed with 50 ml of ethanol with stirring, and filtered again. The precipitate thus obtained was transferred to a 100-ml eggplant-shaped flask, 60 ml of acetonitrile was added, and the mixture was heated with stirring in an oil bath at a bath temperature of 100°C for 1 hour. The mixture was cooled to room temperature and the precipitate was filtered, washed with 30 ml of acetonitrile and 30 ml of ethanol, and dried under reduced pressure at 80°C for 5 hours to give 1.8 g of yellow crystals. An MS analysis identified the yellow crystal as tris(2-phenylpyridine)iridium(III) or ortho-metalated iridium complex (2) represented by chemical formula (2): yield, 68percent; purity by HPLC, 99percent; MS (ESI-TOFMS), 655.; Example 2; In a three-necked flask equipped with a reflux condenser was placed 100 ml of glycerin and the flask was swept free of air by blowing N2 for 3.5 hours. Thereafter, 2.0 g of iridium(III) acetylacetonate, 7.5 g of 2-phenylpyridine, and 3.3 g of tartaric acid were added and, in a nitrogen atmosphere, the mixture was heated under reflux in an oil bath at a bath temperature of 200-210°C with stirring for 44 hours. Upon completion of the reaction, the mixture was cooled to room temperature, 30 ml of ethanol and 300 ml of 2N HCl were added, the mixture was stirred, and the precipitate was filtered. The precipitate was transferred to a beaker, washed with 50 ml of ethanol with stirring, and filtered again. The precipitate thus obtained was transferred to a 100-ml eggplant-shaped flask, 60 ml of acetonitrile was added, and the mixture was heated with stirring in an oil bath at a bath temperature of 100°C for 1 hour. The mixture was cooled to room temperature and the precipitate was filtered, washed with 30 ml of acetonitrile and 30 ml of ethanol, and dried under reduced pressure at 80°C for 5 hours to give 2.2 g of yellow crystals. An MS analysis identified the yellow crystal as ortho-metalated iridium complex (2): yield, 83percent; purity by HPLC, 99percent; MS (ESI-TOFMS), 655; .Example 3; In a three-necked flask equipped with a reflux condenser was placed 100 ml of glycerin and the flask was swept free of air by blowing with N2 for 3.5 hours. Thereafter, 2.0 g of iridium(III) acetylacetonate, 7.5 g of 2-phenylpyridine, and 9 g of tartaric acid were added and, in a nitrogen atmosphere, the mixture was heated under reflux in an oil bath at a bath temperature of 200-210°C with stirring for 5 hours. Upon completion of the reaction, the mixture was cooled to room temperature, 30 ml of ethanol and 300 ml of 2N HCl were added, the mixture was stirred, and the precipitate was filtered. The precipitate was transferred to a beaker, washed with 50 ml of ethanol with stirring, and filtered again. The precipitate thus obtained was transferred to a 100-ml eggplant-shaped flask, 60 ml of acetonitrile was added, and the mixture was heated in an oil bath at a bath temperature of 100°C for 1 hour. The mixture was cooled to room temperature and the precipitate was filtered, washed with 30 ml of acetonitrile and 30 ml of ethanol, and dried under reduced pressure at 80°C for 5 hours to give 1.8 g of yellow crystals. An MS analysis identified the yellow crystal as ortho-metalated iridium complex (2): yield, 70percent; purity by HPLC, 99percent; MS (ESI-TOFMS), 655.; Example 4; In a three-necked flask equipped with a reflux condenser was placed 100 ml of glycerin and the flask was swept free of air by blowing N2 for 3.5 hours. Thereafter, 2.0 g of iridium(III) acetylacetonate, 7.5 g of 2-phenylpyridine, and 9 g of tartaric acid were added and, in a nitrogen atmosphere, the mixture was heated under reflux in an oil bath at a bath temperature of 200-210°C with stirring for 10 hours. Upon completion of the reaction, the mixture was cooled to room temperature, 30 ml of ethanol and 300 ml of 2N HCl were added, the mixture was stirred, and the precipitate was filtered. The precipitate was transferred to a beaker, washed with 50 ml of ethanol with stirring, and filtered again. The precipitate thus obtained was transferred to a 100-ml eggplant-shaped flask, 60 ml of acetonitrile was added, and the mixture was heated in an oil bath at a bath temperature of 100°C for 1 hour. The mixture was cooled to room temperature and the precipitate was filtered, washed with 30 ml of acetonitrile and 30 ml of ethanol, and dried under reduced pressure at 80°C for 5 hours to give 2.2 g of yellow crystals. An MS analysis identified the yellow crystal as ortho-metalated iridium complex (2): yield, 85percent; purity by HPLC, 99percent; MS (ESI-TOFMS), 655.
60% for 24 h; AcetoxyacetoneiridiumIr(acac)3 reacts with C^N bidentate ligand compound 1 for 24 hours.Column-chromatography was used to obtain the electrically neutral light-emitting ring metal iridium complex 2 .The yield is 60percent.
Reference: [1] Patent: EP1944308, 2008, A1, . Location in patent: Page/Page column 8
[2] Patent: EP1944308, 2008, A1, . Location in patent: Page/Page column 7-8
[3] Patent: CN106117270, 2016, A, . Location in patent: Paragraph 0025
[4] Journal of Physical Chemistry A, 2006, vol. 110, # 40, p. 11440 - 11445
  • 5
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YieldReaction ConditionsOperation in experiment
71% at 180℃; for 17 h; Inert atmosphere 145.3 mg (0.3 mmol) of the iridium compound (Ir-1), 279.0 mg (1.8 mmol) of the ligand (L-1), and 2.5 ml of ethylene glycol were placed in a three-necked flask, Under heating at 180 ° C. for 17 hours. After completion of the reaction, the reaction solution was cooled to room temperature, and the precipitated yellow solid was washed with methanol. From the analysis result of 1 H-NMR, the yellow solid precipitated was a mixture of (T-1) and (D-1). The yields of (T-1) and (D-1) were calculated to be 71percent and 22percent, respectively, from the integrated value of 1 H-NMR.
Reference: [1] Patent: JP2017/226634, 2017, A, . Location in patent: Paragraph 0085
  • 6
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YieldReaction ConditionsOperation in experiment
0.29 g With sodium carbonate In glycerol at 240℃; for 12 h; Inert atmosphere Bis[1,2-diphenyl-1H-benzo[d]-imidazole](2-phenylpyridine)iridium(III) [Ir(ppy)2pbi]: Hppy (0.31 g, 2.0 mmol) was dissolved into a mixed solution of 2-ethoxyethanol (12 mL) and water (4 mL) in a 25 mL round bottomed flask, and then IrCl3·3H2O (0.28 g, 0.8 mmol) was added. The mixture was stirred under nitrogen at 120 °C for 12 h. The mixture was cooled to room temperature and the precipitate was collected and washed with water, ethanol, and acetone, then dried in vacuum to give a cyclometalated Ir-μ-chloro-bridged dimer. The dimer complex, Hpbi (0.27 g, 1.0 mmol), Na2CO3 (0.34 g, 3.2 mmol) and 5mL glycerol were charged into a round bottomed flask, the mixture was then heated to 240 °C under an argon atmosphere for another 12 h. After cooling to room temperature, the mixture was poured into 100 mL water, yellow precipitate was filtered off and washed with water, ethanol and ether. The crude product was purified by silica column chromatography with dichloromethane/petroleum ether (1:2, v/v) as the eluent to give 0.29 g Ir(ppy)2pbi as a yellow powder. Yield: 47.5percent, 0.14 g. Ir(ppy)3 can also be obtained as a byproduct, yield: 27.5percent. 1HNMR (CDCl3, 600MHz): 7.90 (t, J=6.4Hz, 2H), 7.85 (d, J=4.8Hz, 1H), 7.77 (d, J=5.4Hz, 1H), 7.69–7.59 (m, 7H), 7.50–7.47 (m, 2H), 7.06 (t, J=7.8Hz, 1H), 6.97 (d, J=7.8Hz, 1H), 6.92–6.78 (m, 10H), 6.72 (t, J=7.8Hz, 1H), 6.63 (d, J=7.8Hz, 1H), 6.53 (t, J=7.8Hz, 1H), 6.05 (d, J=8.4Hz, 1H); 13CNMR (CDCl3, 150MHz): 167.65, 166.68, 163.39, 162.61, 161.33, 148.06, 144.33, 143.92, 140.86, 137.90, 137.85, 136.91, 136.87, 136.32, 135.90, 135.80, 134.10, 130.38, 130.13, 129.89, 129.78, 129.74, 128.53, 128.17, 125.25, 123.94, 123.72, 123.23, 122.38, 122.00, 121.29, 119.66, 119.52, 119.09, 118.66, 118.54, 115.23, 110.53; HRMS (APCI): m/z calcd for C41H29IrN4: 770.2021; found: 771.2094 (M+H)+.
Reference: [1] Dyes and Pigments, 2015, vol. 113, p. 649 - 654
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YieldReaction ConditionsOperation in experiment
22% at 180℃; for 17 h; Inert atmosphere 167.0 mg (0.3 mmol) of the iridium compound (Ir-2), 162.7 mg (1.05 mmol) of the ligand (L-1), and 2.5 ml of ethylene glycol were placed in a three-necked flask, Under heating at 180 ° C. for 17 hours. After completion of the reaction, the reaction solution was cooled to room temperature, and the precipitated yellow solid was washed with methanol. From the analysis result of 1 H-NMR, the yellow solid precipitated was a mixture of (T-1) and (D-1). The yields of (T-1) and (D-1) were calculated to be 22percent and 73percent, respectively, from the integrated value of 1 H-NMR.
Reference: [1] Patent: JP2017/226634, 2017, A, . Location in patent: Paragraph 0087
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Reference: [1] Chemical Science, 2013, vol. 4, # 3, p. 1175 - 1181
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Reference: [1] Chemical Communications, 2008, vol. 8, # 5, p. 618 - 620
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Reference: [1] Patent: WO2004/99223, 2004, A1, . Location in patent: Page/Page column 23-25
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Reference: [1] Inorganica Chimica Acta, 2007, vol. 360, # 11, p. 3493 - 3498
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Reference: [1] Angewandte Chemie - International Edition, 2016, vol. 55, # 5, p. 1872 - 1875[2] Angew. Chem., 2016, vol. 128, # 5, p. 1904 - 1907,4
  • 13
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Reference: [1] Dyes and Pigments, 2015, vol. 113, p. 649 - 654
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Reference: [1] Patent: WO2004/99223, 2004, A1, . Location in patent: Page/Page column 22-23
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Reference: [1] RSC Advances, 2015, vol. 5, # 61, p. 49466 - 49470
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