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[ CAS No. 654664-63-8 ] {[proInfo.proName]}

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Chemical Structure| 654664-63-8
Chemical Structure| 654664-63-8
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Product Details of [ 654664-63-8 ]

CAS No. :654664-63-8 MDL No. :MFCD16660186
Formula : C18H13BO2 Boiling Point : -
Linear Structure Formula :- InChI Key :PXFBSZZEOWJJNL-UHFFFAOYSA-N
M.W : 272.11 Pubchem ID :59805119
Synonyms :

Calculated chemistry of [ 654664-63-8 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 21
Num. arom. heavy atoms : 18
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 2.0
Molar Refractivity : 88.79
TPSA : 40.46 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.28 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 3.78
Log Po/w (WLOGP) : 2.83
Log Po/w (MLOGP) : 3.06
Log Po/w (SILICOS-IT) : 2.41
Consensus Log Po/w : 2.41

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -4.48
Solubility : 0.00908 mg/ml ; 0.0000334 mol/l
Class : Moderately soluble
Log S (Ali) : -4.32
Solubility : 0.0129 mg/ml ; 0.0000475 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -6.32
Solubility : 0.000132 mg/ml ; 0.000000484 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.18

Safety of [ 654664-63-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 654664-63-8 ]

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

  • Downstream synthetic route of [ 654664-63-8 ]

[ 654664-63-8 ] Synthesis Path-Downstream   1~19

  • 1
  • [ 1235873-06-9 ]
  • [ 654664-63-8 ]
  • [ 1235874-98-2 ]
YieldReaction ConditionsOperation in experiment
70% With potassium phosphate;dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; tris-(dibenzylideneacetone)dipalladium(0); In water; toluene;Inert atmosphere; Reflux; Example 6; Synthesis of Compound 39 Step 1. The mixture of 3-chloro-6-bromo-[1]benzothieno[2,3-c]pyridine (1.7 g, 5.8 mmol), triphenylen-2-ylboronic acid (1.6 g, 5.8 mmol), potassium phosphate tribasic (3.7 g, 17 mmol), 200 mL toluene and 10 mL water was prepared and bubbled with nitrogen for twenty minutes. Then the tris(dibenzylideneacetone)dipalladium (53 mg, 0.060 mmol) and 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (96 mg, 0.23 mmol) were added. The mixture was bubbled with nitrogen for another twenty minutes. After refluxed overnight under nitrogen, then reaction mixture was cooled to room temperature and filtered through a silica plug and washed with dichloromethane. The first several portions were discarded since they only contained impurities. The combined filtrate was concentrated to give crude product, which was recrystallized from hot dichloromethane and hexanes to give 1.8 g 3-chloro-6-(2-triphenyleneyl)-[1]Benzothieno[2,3-c]pyridine as yellow solid (4.0 mmol, 70% yield).
  • 2
  • [ 654664-63-8 ]
  • [ 1235873-15-0 ]
  • [ 1235875-81-6 ]
YieldReaction ConditionsOperation in experiment
81% With potassium phosphate;dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; tris-(dibenzylideneacetone)dipalladium(0); In water; toluene;Inert atmosphere; Reflux; Example 7; Synthesis of Compound 59 Step 1. The mixture of 1-chloro-6-(9-carbazole)-[1]benzothieno[2,3-c]pyridine (1.0 g, 1.6 mmol), triphenylen-2-ylboronic acid (0.85 g, 3.1 mmol), potassium phosphate tribasic (1.7 g, 7.8 mmol), 100 mL toluene and 5 mL water was prepared and bubbled with nitrogen for twenty minutes. Then the tris(dibenzylideneacetone)dipalladium (24 mg, 0.030 mmol) and 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (43 mg, 0.10 mmol) were added. The mixture was bubble with nitrogen for another twenty minutes. After refluxed overnight under nitrogen, the reaction was cooled to room temperature and concentrated. The obtained solid was redissolved in 800 mL refluxing toluene and filtered through a thin celite plug. The collected filtrate was concentrated to about 100 mL and then refluxed under nitrogen for one hour. After slowly cooled to room temperature, the precipitation was collected by filtration. The residue was stirred in 100 mL hot mixture of 20% dichloromethane in methanol and stirred overnight after it cooled to room temperature. The residue was collected by filtration and dried under vacuum to provide 1.2 g white solid (2.1 mmol, 81% yield).
  • 3
  • 1-chlorobenzo[4,5]thieno[2,3-c]pyridine [ No CAS ]
  • [ 654664-63-8 ]
  • [ 1235877-04-9 ]
YieldReaction ConditionsOperation in experiment
84% With potassium phosphate;dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; tris-(dibenzylideneacetone)dipalladium(0); In water; toluene;Inert atmosphere; Reflux; Example 9; Synthesis of Compound 70 Step 1. The mixture of 1-chloro-benzothieno[2,3-c]pyridine (1.0 g, 4.5 mmol), 2-triphenylene-boronic acid (1.25 g, 4.5 mmol), synthesized according to U.S. Provisional Application Ser. No. 60/963,944, potassium phosphate tribasic (3.0 g, 18.0 mmol), 100 mL toluene and 10 mL water was prepared and bubbled with nitrogen for fifteen minutes. Then the tris(dibenzylideneacetone)dipalladium (42 mg, 0.045 mmol) and 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (77 mg, 0.18 mmol) were added. The mixture was bubbled with nitrogen for another twenty minutes. After refluxed overnight under nitrogen, the reaction mixture was cooled to room temperature. The product was purified by silical gel chromatography column. 1.5 g (84%) Compound 70 was obtained.
  • 4
  • [ 121-43-7 ]
  • [ 19111-87-6 ]
  • [ 654664-63-8 ]
YieldReaction ConditionsOperation in experiment
57% The intermediates in argon atmosphere (E1) (2.90g, 9 . 44mmol), tetrahydrofuran (80 ml) mixing, cooling to -78 C. Furthermore, by adding n-BuLi (1.60M hexane solution, 6.20 ml, 9 . 91mmol), with 2-hour heating to 0 C. Then again cooling to -78 C, adding trimethoxyborane (2.58g, 24 . 8mmol), at -78 C stirring 20 minutes, with 8 hours warming to room temperature. After the reaction, adding hydrochloric acid aqueous solution (1M, 20 ml), stirring at room temperature 1 hour, extraction with ethyl acetate. The solution after drying with magnesium sulfate, concentrated, in hexane is suspended in the washing, filtering and recycling, got the midbody (E2) (1.46g, 5 . 38mmol, yield 57%).
57% Under an argon atmosphere the intermediate (A2) (2.90g, 9.44mmol), tetrahydrofuran (80mL) were mixed and cooled to -78 deg C. Then, added a solution of n-butyllithium (1.60M in hexanes, 6.20mL, 9.91mmol), 2 hours with heating until it is 0 deg C. Then cooled again to -78 deg.] C, then was added trimethoxy borane (2.58g, 24.8mmol), stirred for 20 minutes at -78 deg.] C after 8 hours with heating until it is room temperature.After completion of the reaction, aqueous hydrochloric acid (1M, 20mL), stirred at room temperature for 1 hour, extracted with ethyl acetate.The solution was dried over magnesium sulfate, concentrated, suspended in hexanes and washed, recovered by filtration, to give intermediate (A3)(1.46g, 5.38mmol, 57% yield)
Preparation of Compound (118)In tetrahydrofuran (280 mL), 1-bromotriphenylene (Compound 117) (10.6 g, 34.5 mmol) was dissolved under nitrogen atmosphere, and n-BuLi (2.5 M in n-hexane) (17.9 mL, 44.9 mmol) was slowly added dropwise thereto at -78 C. After stirring for 1 hour, trimethyl borate (7.2 g, 69 mmol) was added at low temperature, and the mixture was stirred while slowly raising the temperature to 25 C. After stirring for 16 hours, 10 M hydrochloric acid (30 mL) was added thereto. The resultant mixture was stirred for 1 hour, extracted with ethyl acetate (200 mL). The extract was washed with water (200 mL), dried over anhydrous magnesium sulfate, and the organic layer was evaporated under reduced pressure. The solid obtained was recrystallized from hexane (100 mL), and the filtered solid was dried under reduced pressure to obtain Compound (118) (9.0 g, 33.0 mmol).
To a flask including 2-bromotriphenylene, tetrahydrofuran (0.1 M) was added and then cooled to about -78 C. Then, 1.2 eq. of n-butyl lithium (n-BuLi, dissolved in hexane with a concentration of 1.6 M) was added and then stirred for about 30 minutes. 1.2 eq. of methylborate was added at the same temperature, and then, the temperature was gradually increased to ambient temperature. After stirring for about 1 hour, 50 ml of a 1N HCl solution was gradually added and then stirred for about 10 minutes. An organic layer was extracted with ethyl acetate (EA) and washed with distilled water. The product thus obtained was dried with magnesium sulfate (MgSO4) and distilled under a reduced pressure. The residue was recrystallized using ethyl acetate (EA):hexane (Hex) in a ratio of 1:10 to produce a triphenylen-2-ylboronic acid intermediate (Yield 77.4%). The mass of the compound identified using a high resolution mass spectrometer (HRMS) was 271. [HRMS for C18H13BO2 [M]+: calcd: 272.11, found: 271].

  • 5
  • [ 83-53-4 ]
  • [ 654664-63-8 ]
  • [ 1158227-46-3 ]
YieldReaction ConditionsOperation in experiment
With sodium carbonate;trans-bis(triphenylphosphine)palladium dichloride; In toluene; at 100℃; for 3h; Preparation of Compound (119)Compound (118) (9.2 g, 33.9 mmol), 1,4-dibromonaphthalene (8.8 g 30.8 mmol) and trans-dichlorobistriphenylphosphine palladium (II) (Pd(PPh3)2Cl2 (2.1 g, 3.1 mmol) were dissolved in toluene (300 mL). After adding 2 M sodium carbonate solution (150 mL), the mixture was heated to 100 C., and reacted at the same temperature for 3 hours. The reaction mixture was extracted with dichloromethane (300 mL), and the extract was washed with aqueous sodium chloride solution (300 mL), dried over anhydrous magnesium sulfate, and filtered. After evaporating the organic layer under reduced pressure, the solid obtained was recrystallized from tetrahydrofuran (100 mL) to obtain the desired compound (119) (7.7 g, 17.7 mmol).
  • 6
  • [ 654664-63-8 ]
  • [ 1158227-50-9 ]
  • 7
  • [ 654664-63-8 ]
  • [ 1158227-53-2 ]
  • 8
  • [ 654664-63-8 ]
  • [ 854952-59-3 ]
  • [ 1313400-54-2 ]
YieldReaction ConditionsOperation in experiment
90% With potassium carbonate;palladium diacetate; tris-(o-tolyl)phosphine; In ethanol; water; toluene; at 80℃; for 3h;Inert atmosphere; Example 5In this example, an example in which 9-phenyl-3-[3-(triphenylen-2-yl)-phenyl]-9H-carbazole (abbreviation: mPCzPTp) represented by Structural Formula (111) in Embodiment 1 is manufactured will be described. In a 50-mL three-neck flask, a mixture of 0.7 g (1.8 mmol) of 3-bromo-9-phenyl-9H-carbazole, 0.5 g (1.8 mmol) of triphenylene-2-boronic acid, 4.1 mg (18 mumol) of palladium(II) acetate, 28 mg (92 mumol) of tri(o-tolyl)phosphine, 6.9 mL of toluene, 2.3 mL of ethanol, and 1.9 mL of a potassium carbonate aqueous solution (2 mol/L) was deaerated while being stirred under reduced pressure, and then heated and stirred in a nitrogen atmosphere at 80 C. for 3 hours to be reacted.After the reaction, an aqueous layer of the obtained suspension was extracted with toluene. The obtained extracted solution and the suspension were washed together with saturated saline, and then magnesium sulfate was added to the obtained solution so that moisture was adsorbed. The suspension was separated by gravity filtration, and the filtrate was concentrated to give an oily substance. This oily substance was purified by silica gel column chromatography. The column chromatography was performed first using a mixed solvent of toluene and hexane (toluene:hexane=1:9) as a developing solvent, and then using a mixed solvent of toluene and hexane (toluene:hexane=1:6) as a developing solvent. The obtained fractions were concentrated to give an oily substance. Toluene and hexane were added to the oily substance, and the mixture was crystallized to give 0.9 g of a white solid that was an objective substance in a yield of 90%. The reaction scheme of the synthesis method is shown in (F5-1). The obtained compound was examined by a nuclear magnetic resonance (NMR) method. The measurement data are shown below.1H NMR (CDCl3, 300 MHz): delta (ppm)=7.30-7.54 (m, 5H), 7.60-7.80 (m, 12H), 8.01 (dd, J=8.4 Hz, 1.5 Hz, 1H), 8.14 (s, 1H), 8.23 (d, J=7.8 Hz, 1H), 8.47 (d, J=2.1 Hz, 1H), 8.67-8.80 (m, 5H), 8.95 (d, J=1.5 Hz, 1H).FIGS. 20A and 20B are 1H NMR charts. Note that FIG. 20B is a chart showing an enlarged part of FIG. 20A in the range of 7.0 ppm to 9.0 ppm. The measurement results confirmed that mPCzPTp that was the objective substance was able to be obtained.FIG. 21A shows an absorption spectrum of mPCzPTp in a toluene solution of mPCzPTp, and FIG. 21B shows an emission spectrum thereof. FIG. 22A shows an absorption spectrum of a thin film of mPCzPTp, and FIG. 22B shows an emission spectrum thereof. The absorption spectrum was measured with a UV-visible spectrophotometer (V550, produced by JASCO Corporation). The emission spectrum was measured with a fluorescence spectrophotometer (FS920, produced by Hamamatsu Photonics Corporation). The measurements were performed with samples prepared in such a manner that the solution was put in a quartz cell while the thin film was obtained by evaporation onto a quartz substrate. FIG. 21A show the absorption spectrum of mPCzPTp in the solution of mPCzPTp which was obtained by subtracting the absorption spectra of the quartz cell and toluene put therein, and FIG. 22A shows the absorption spectrum of the thin film which was obtained by subtracting the absorption spectrum of the quartz substrate. In FIGS. 21A and 21B and FIGS. 22A and 22B, the horizontal axis represents wavelength (nm) and the vertical axis represents intensity (arbitrary unit). In the case of the toluene solution, the absorption peak was observed at around 290 nm, and the maximum emission wavelength was 381 nm (excitation wavelength: 290 nm). In the case of the thin film, the absorption peak was observed at around 277 nm, and the maximum emission wavelength was 397 nm (excitation wavelength: 306 nm).The absorption spectrum showed that mPCzPTp described in this example is a material having weak absorption of light in the visible region. In addition, the emission spectrum shows that mPCzPTp exhibits blue-violet emission.
  • 9
  • [ 3934-20-1 ]
  • [ 654664-63-8 ]
  • [ 1369587-65-4 ]
YieldReaction ConditionsOperation in experiment
20% With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; at 120℃; for 7h; In a flask, 2,4-dichloropyrimidine (9.7g, 65.1mmol), Compound 7-1 (17.72g, 65.1mmol), Pd(PPh3)4 (3.76g, 3.25mmol), Na2CO3 (20.7g, 195.3mmol) and DME 1.5L were placed and dissolved, and the mixture was stirred at 120C for 7 hours. After reaction, distilled water was slowly added so that the reaction was terminated, and the organic layer was obtained via extraction using EA, and the residual moisture was removed using anhydrous MgSO4. Subsequently, drying and column separation were performed, yielding Compound 7-2 (4g, 20%).
  • 10
  • [ 19111-87-6 ]
  • [ 654664-63-8 ]
YieldReaction ConditionsOperation in experiment
55% 2-bromotriphenylene (63.7, 207.4mmol) was dissolved in THF 1.5L and cooled to -78C. 10 minutes later, n-BuLi(2.5M in hexane) (125mL, 311mmol) was slowly added and the mixture was stirred for 1 hour. Triethylborate (67mL, 311mmol) was slowly added, and the mixture was stirred for 24 hours. After termination of the reaction, 1M HCl was added, and the mixture was extracted with EA. Subsequently, the residual moisture was removed using anhydrous MgSO4, after which drying and recrystallization from hexane were carried out, yielding Compound 7-1 (31.8g, 55%).
  • 11
  • [ 40102-86-1 ]
  • [ 654664-63-8 ]
  • [ 1375600-89-7 ]
YieldReaction ConditionsOperation in experiment
50% With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; water; toluene; for 3h;Inert atmosphere; Reflux; Synthesis of illustrative compound A-13[0138]toluene/EtOH/H20F-1 A-13[0139] A 200-mL recovery flask was charged with the following reagents and solvents:F-1: 1.85 g (5 mmol)F-7: 4.3 g (12 mmol)Tetrakis (triphenylphosphine) palladium ( 0 ) : 137 mg (0.12 mmol)Toluene: 50 mLEthanol: 20 mLSodium carbonate aqueous solution (concentration: 30% by weight) : 30 mL[0140] hen, the atmosphere inside the reaction system was replaced by a nitrogen atmosphere, and thereafter, the reaction solution was stirred under refluxing for 3 hours. After the completion of the reaction, water was added to the reaction solution and further stirred, and a deposited crystal was filtered out. Then, thecrystal was washed with water, ethanol and acetone successively to obtain a crude product. Then, the crude product was heated and dissolved in chlorobenzene, and hot filtered, and thereafter, recrystallized twice with a chlorobenzene solvent to obtain a purified crystal. Then, the obtained crystal was vacuum dried at 120C to obtain 1.7 g of high-purity illustrative compound A-13 (yield: 50%) .[0141] [MALDI-TOF-MS]Observed value: m/z = 674.98, calculated value: 664.19
  • 12
  • [ 654664-63-8 ]
  • 2-(10-bromoanthracen-9-yl)triphenylene [ No CAS ]
  • 13
  • [ 654664-63-8 ]
  • 4,4,5,5-tetramethyl-2-(10-(triphenylene-2-yl)anthracen-9-yl)-1,3,2-dioxaborolan [ No CAS ]
  • 14
  • [ 1564-64-3 ]
  • [ 654664-63-8 ]
  • 2-(anthracen-9-yl)triphenylene [ No CAS ]
YieldReaction ConditionsOperation in experiment
3.3g With potassium phosphate; tetrakis(triphenylphosphine) palladium(0); for 8h;Inert atmosphere; Reflux; Under the nitrogen atmosphere, triphenylen-2-ylboronic acid (5.6 g), 9-bromoanthracene (3.5 g), (Pd(PPh3)4) (0.5 g), potassium phosphate (5.8 g), and a mixture solvent of pseudo cumene, t-butyl alcohol, and water (48 ml) (pseudo cumene/t-butyl alcohol/water = 10/1/1 (volume ratio)) were added to a flask and then refluxed for 8 hours. After adding water, the precipitates were collected by suction filtration. The obtained solid was washed with water followed by methanol and purified by silica gel column chromatography (solvent: toluene). After re-crystallization with a mixture solution of toluene/ethyl acetate, 2-(anthracen-9-yl)triphenylene (3.3 g) was obtained as an eleventh intermediate compound. The scheme is represented in the following 'Reaction 21'.
  • 15
  • [ 654664-63-8 ]
  • 7-(10-(naphthalen-1-yl)anthracen-9-yl)naphthalen-2-yl trifluoromethane sulfonate [ No CAS ]
  • 2-(7-(10-(naphthalene-1-yl)anthracen-9-yl)naphthalene-2-yl)triphenylene [ No CAS ]
YieldReaction ConditionsOperation in experiment
1.9 g With potassium phosphate; bis(dibenzylideneacetone)-palladium(0); tricyclohexylphosphine; In ethanol; water; toluene; for 2h;Inert atmosphere; Reflux; Under the nitrogen atmosphere, 7-(10-(naphthalen-1-yl)anthracen-9-yl)naphthalen-2-yl trifluoromethane sulfonate (3.0 g) as the fifth intermediate compound, 2-triphenylene boronic acid (2.1 g), Pd(dba)2 (0.03 g), tricyclohexyl phosphine (0.03 g), potassium phosphate (2.2 g), and a mixture solvent (22 ml) of toluene, ethanol and water (toluene/ethanol/water = 9/1/1 (volume ratio)) were added to a flask and refluxed for 2 hours. Once the heating is completed, the reaction solution was cooled to room temperature and added with methanol. The precipitates were collected by suction filtration. The obtained solid was washed with water followed by methanol, and washed further with ethyl acetate. The obtained crude product was dissolved in chlorobenzene, and colored components were removed by passing through a silica gel short column. After re-crystallization with chlorobenzene, 2-(7-(10-(naphthalen-1-yl)anthracen-9-yl)naphthalen-2-yl)triphenylene (1.9 g) was obtained as the target compound represented by Formula (1-38). The scheme is shown in the following 'Reaction 10'. According to NMR measurement, structure of the target compound (1-38) was determined. 1H-NMR (CDCl3): delta = 9.75 (s, 1H), 8.68-8.90 (m, 6H), 8.38 (m, 1H), 8.02-8.30 (m, 8H), 7.60-7.90 (m, 10H), 7.53 (m, 3H), 7.35 (m, 3H).
  • 16
  • [ 654664-63-8 ]
  • [ 1593236-14-6 ]
  • [ 1593236-15-7 ]
YieldReaction ConditionsOperation in experiment
79% With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate; In toluene; for 8h;Reflux; The following reagents and a solvent were charged in a 100-ml eggplant flask.Intermediate NPCRY-1: 389 mg (1.0 mmol)Boronic acid compound TRP-2: 272 mg (1.0 mmol)Palladium(II) acetate: 18 mg (80 micromoles)Dicyclohexyl(2?,6?-dimethoxybiphenyl-2-yl)phosphine: 80 mg (194 micromoles)Potassium phosphate: 0.53 g (2.5 mmol)Toluene: 10 mlThe resulting reaction solution was heated to reflux for 8 hours while being stirred. After the reaction was completed, water was added in the reaction solution in order to separate phases. The residue was purified by silica gel column chromatography (developing solvent: heptane/toluene = 4/1) and recrystallized using a mixture solvent of toluene and ethanol. The resulting crystal was vacuum-dried at 150 degrees Celsius and then purified by sublimation. Thus, 458 mg (yield 79%) of Example Compound L105 was prepared. The purity of Example Compound L-105 determined by HPLC was 99% or more. The results of identification of Example Compound L- 105 are shown below.MALDI-TOF-MS (matrix assisted laser desorption/ionization-time of flight mass spectrometry) with Autoflex LRF produced by Bruker CorporationMeasured value = 580.01Calculated value = 580.22
79% With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate; In water; toluene; for 8h;Reflux; The following reagents and solvents were loaded in a 100-ml recovery flask. Intermediate NPCRY-1: 389 mg (1.0 mmol) Boronic acid compound TRP-2: 272 mg (1.0 mmol) Palladium ( II ) acetate: 18 mg (80 muetaalphaomicron) Dicyclohexyl (2 ' , 6 ' -dimethoxybiphenyl-2-yl ) phosphine : 80 mg (194 mol) Potassium phosphate: 0.53 g (2.5 mmol) Toluene: 10 ml Water: 2 ml Next, the reaction solution was heated to reflux for 8 hours while being stirred. After the completion of the reaction, water was added to the resultant, a liquid- separating operation was performed, and an organic layer was recovered. Next, the recovered organic layer was dried and then the solvent was removed by distillation under reduced pressure, whereby a crude product was obtained. Next, the crude product was purified by silica gel column chromatography (developing solvent: heptane/toluene=4/l) and was then recrystallized with toluene/ethanol to provide a crystal. Next, the resultant crystal was vacuum-dried at 150C and then subjected to sublimation purification to provide 458 mg of Exemplified Compound L-105 (yield: 79%). The resultant compound was evaluated for its purity by employing HPLC. As a result, it was confirmed that the purity was 99% or more. MALDI-TOF MS confirmed that the compound had an M+ of 580.2.
  • 17
  • [ 654664-63-8 ]
  • [ 817210-33-6 ]
  • [ 1616510-99-6 ]
YieldReaction ConditionsOperation in experiment
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate; In ethanol; water; toluene; for 8h;Reflux; The following reagents and solvents were loaded in a 100-ml recovery flask. Intermediate NPCRY-1: 389 mg (1.0 mmol) Boronic acid compound TRP-2: 272 mg (1.0 mmol) Palladium ( II ) acetate: 18 mg (80 muetaalphaomicron) Dicyclohexyl (2 ' , 6 ' -dimethoxybiphenyl-2-yl ) phosphine : 80 mg (194 mol) Potassium phosphate: 0.53 g (2.5 mmol) Toluene: 10 ml Water: 2 ml Next, the reaction solution was heated to reflux for 8 hours while being stirred. After the completion of the reaction, water was added to the resultant, a liquid- separating operation was performed, and an organic layer was recovered. Next, the recovered organic layer was dried and then the solvent was removed by distillation under reduced pressure, whereby a crude product was obtained. Next, the crude product was purified by silica gel column chromatography (developing solvent: heptane/toluene=4/l) and was then recrystallized with toluene/ethanol to provide a crystal. Next, the resultant crystal was vacuum-dried at 150C and then subjected to sublimation purification to provide 458 mg of Exemplified Compound L-105 (yield: 79%). The resultant compound was evaluated for its purity by employing HPLC. As a result, it was confirmed that the purity was 99% or more. MALDI-TOF MS confirmed that the compound had an M+ of 580.2. Exemplified Compound J-105 was obtained by the same method as that of Synthesis Example 6 except that in Synthesis Example 6, NP-3 was used instead of CRY-2 and TRP-2 was used instead of NP-2. he resultant compound was evaluated for its purity by employing HPLC. As a result, it was confirmed that the purity was 99% or more. MALDI-TOF MS confirmed that the compound had an M+ of 606.2.
  • 18
  • [ 654664-63-8 ]
  • C38H21BrN2S2 [ No CAS ]
  • C56H32N2S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
86.4% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In toluene; for 12h;Heating; Synthesis Example 11:10 g (1 eq, 0.0154 mol) of H-1 and 4.6 g (1.1 eq, 0.0169 mol) of H-2 were added to a flask and dissolved in 450 m? of Toluene. 0.35 g (0.02 eq, 0.00031 mmol) of Pd(PPh3)4, and 45 ml of 2 M K2CO3 solution were added to the flask to prepare a mixture, and the mixture was thermally agitated for 12 hours to prepare a reaction solution. The reaction solution was filtered through Celite and then subjected to a column chromatography to obtain 10.59 g (yield rate = 86.4%) of Compound 18. [0154] Elemental Analysis for C56H32N2S2 : calcd : C, 84.39; H, 4.05; N, 3.51; S, 8.05. [0155] HRMS for C56H32N2S2 [M]+: calcd 796.2, found 796.
  • 19
  • [ 654664-63-8 ]
  • C25H19ClN2 [ No CAS ]
  • C43H30N2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
25% With potassium phosphate monohydrate; bis(tri-t-butylphosphine)palladium(0); In 1,4-dioxane; water; for 24h;Reflux; [0114] Structural Formula C (12.0 g, 31.3 mmol), Structural Formula G (9.4 g, 34.4 mmol), K3PO4·H2O (20.0 g, 94.4mmol), Pd(p-tBu3)2 (0.16 g, 0.31 mmol), 1,4-dioxane (100 mL), and H2O (30 ml) were mixed, refluxing was performedfor 24 hours, and cooled to normal temperature. After the water layer was removed, the organic layer was distilled underreduced pressure. The generated solid was purified by the chromatography to obtain Chemical Formula 1-55 (4.5 g,yield 25%).MS: [M+H]+ = 575
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