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[ CAS No. 876442-90-9 ] {[proInfo.proName]}

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Chemical Structure| 876442-90-9
Chemical Structure| 876442-90-9
Structure of 876442-90-9 * Storage: {[proInfo.prStorage]}
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Product Details of [ 876442-90-9 ]

CAS No. :876442-90-9 MDL No. :MFCD26406213
Formula : C16H13BO2 Boiling Point : -
Linear Structure Formula :- InChI Key :XDKCHGWZDWHBQO-UHFFFAOYSA-N
M.W : 248.08 Pubchem ID :57539613
Synonyms :

Calculated chemistry of [ 876442-90-9 ]

Physicochemical Properties

Num. heavy atoms : 19
Num. arom. heavy atoms : 16
Fraction Csp3 : 0.0
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 2.0
Molar Refractivity : 79.21
TPSA : 40.46 Ų

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) : -5.19 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 3.7
Log Po/w (WLOGP) : 2.19
Log Po/w (MLOGP) : 2.72
Log Po/w (SILICOS-IT) : 1.93
Consensus Log Po/w : 2.11

Druglikeness

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

Water Solubility

Log S (ESOL) : -4.2
Solubility : 0.0156 mg/ml ; 0.0000631 mol/l
Class : Moderately soluble
Log S (Ali) : -4.24
Solubility : 0.0143 mg/ml ; 0.0000575 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -5.49
Solubility : 0.00081 mg/ml ; 0.00000327 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 1.95

Safety of [ 876442-90-9 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 876442-90-9 ]

* 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 [ 876442-90-9 ]

[ 876442-90-9 ] Synthesis Path-Downstream   1~41

  • 1
  • [ 876442-90-9 ]
  • [ 591-18-4 ]
  • [ 911390-64-2 ]
YieldReaction ConditionsOperation in experiment
71% With sodium carbonate In 1,2-dimethoxyethane; water; toluene at 20℃; for 8h; Heating / reflux;
  • 2
  • [ 22082-94-6 ]
  • [ 876442-90-9 ]
YieldReaction ConditionsOperation in experiment
94% Stage #1: 6-phenyl-2-bromonaphthalene With n-butyllithium In diethyl ether; hexane; toluene at -40 - -5℃; for 1h; Stage #2: With Triisopropyl borate In diethyl ether; hexane; toluene at 20℃; for 4h; Stage #3: With hydrogenchloride In diethyl ether; hexane; water; toluene
55% Stage #1: 6-phenyl-2-bromonaphthalene With n-butyllithium In tetrahydrofuran; diethyl ether; hexane at -20℃; for 1h; Inert atmosphere; Stage #2: With Triisopropyl borate In tetrahydrofuran; diethyl ether; hexane at -60 - 20℃; for 16h; Inert atmosphere; Stage #3: With hydrogenchloride In tetrahydrofuran; diethyl ether; hexane; water at 20℃; for 1h; 5.2 [Synthesis Reference 5-2] Synthesis of 6-phenylnaphthalene-2-boronic acid Under an argon gas atmosphere, a mixture of 100.0 g (353.1 mmol) of 2-bromo-6-phenylnaphthalene, 1.2 L of dehydrated THF and 1.2 L of dehydrated diethyl ether was cooled down to minus 20 degree C. Then, 280 ml (437 mmol) of hexane solution of 1.56M n-butyllithium was dropped into the mixture while the mixture was being stirred. The reaction mixture was further stirred at minus 20 degrees for 1 hour. The reaction mixture was cooled down to minus 60 degrees C., and 199.3 g (1.06 mol) of triisopropylborate was dropped into the mixture. The reaction mixture was warmed up and then stirred at room temperature for 16 hours. The reaction mixture was added with aqueous solution of hydrochloric acid and stirred at room temperature for 1 hour. After the reaction, the reaction mixture was added with toluene, and aqueous phase thereof was eliminated. Then, organic phase thereof was washed with water and dried with magnesium sulfate, and the solvent was distilled away under reduced pressure. By recrystallizing the obtained solid with hexane, 58.0 g of 6-phenylnaphthalene-2-boronic acid was obtained at an yield of 55%.
51% Stage #1: 6-phenyl-2-bromonaphthalene With n-butyllithium In diethyl ether; hexane; toluene at -64℃; for 2.5h; Stage #2: With Trimethyl borate In diethyl ether; hexane; toluene at 20℃; for 12.25h; Stage #3: With hydrogenchloride; water In diethyl ether; hexane; toluene at 0 - 10℃; 6.6-B 6-B. Preparation of compound 6b; [150] Under N atmosphere, to a compound 6a (20 g, 70.6 mmol), dehydrated ether (70 mL) and dehydrated toluene (200 mL) were added, and cooled to -640C in ice bath. A 2.5 M butyl lithium/hexane solution (24 mL) was added drop wise thereto for 30 minutes, and subjected to reaction at -640C for 2 hours. Boronic acid trimethylester (18 mL) was added drop wise thereto for 15 minutes, and then stirred at room temperature for 12 hours. After ice cooling, 2 N hydrochloric acid (500 mL) was added, and stirred for 24 hours. The mixture was separated, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was recrystallized from EtOH to prepare a compound 6b (8.9 g, 51%).
  • 3
  • normal-butyllithium [ No CAS ]
  • 2-bromo-6-iodonaphthanlene [ No CAS ]
  • boronic acid triisopropyl ester [ No CAS ]
  • [ 22082-94-6 ]
  • [ 98-80-6 ]
  • [ 876442-90-9 ]
YieldReaction ConditionsOperation in experiment
94% With sodium chloride In hexane; toluene S.4 Synthesis Example 4 Synthesis Example 4 (Synthesis of AN-22) To 12 g of 2-bromo-6-phenylnaphthalene synthesised in accordance with a conventional process or by the reaction of 2-bromo-6-iodonaphthanlene and phenylboronic acid, 90 ml of anhydrous ether and 30 ml of anhydrous toluene were added, and the reaction system was purged with argon and cooled at -40° C. To the cooled mixture, 29 ml of a 1.6 M hexane solution of normal-butyllithium was added dropwise, and the resultant mixture was stirred for 1 hour. After the obtained mixture was heated to -5° C. and then cooled to -40° C., a solution obtained by diluting 29 ml of boronic acid triisopropyl ester with ether was added dropwise, and the resultant mixture was stirred for 4 hours and then left standing for one night. After the resultant mixture was acidified with a 10% dilute hydrochloric acid, the formed white solid substance was separated by filtration and washed with water and hexane. The amount by weight of white crystals obtained after being dried was 6.8 g. The mother liquor of the filtration was washed with a saturated aqueous solution of sodium chloride and dried with anhydrous sodium sulfate, and the solvent was removed using an evaporator. The obtained light yellow solid substance was washed with methylene chloride and dried, and 3.1 g of white crystals were obtained. The obtained crystals were combined with the crystals obtained above, and 9.9 g of 2-phenylnaphthalene-6-boronic acid was obtained (the yield: 94%).
  • 4
  • [ 130201-21-7 ]
  • [ 876442-90-9 ]
YieldReaction ConditionsOperation in experiment
With sodium chloride; sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In toluene; Synthesis Example 11 (Synthesis of AN-85) Under the atmosphere of argon, 8 g of 2-phenylnaphthalene-6-boronic acid obtained in Synthesis Example 4 and 11.6 g of <strong>[130201-21-7]4-bromo-3'-iodobiphenyl</strong> were dissolved into 150 ml of toluene, and 0.75 g of tetrakis(triphenylphosphine)palladium was added to the obtained solution. To the resultant mixture, 49 ml of a 2 M aqueous solution of sodium carbonate was added, and the obtained mixture was heated under the refluxing condition for 8 hours. After the resultant mixture was left standing for one night, the mixture was subjected to extraction with toluene. The extract was washed with a saturated aqueous solution of sodium chloride, and the solvent was removed using an evaporator.
  • 5
  • [ 876442-90-9 ]
  • [ 1564-64-3 ]
  • [ 944801-20-1 ]
YieldReaction ConditionsOperation in experiment
85% With potassium carbonate In tetrahydrofuran; water for 24h; Heating / reflux; 6.6-C 6-C. Preparation of compound 6c; [152] Under N atmosphere, 9-bromoanthracene (7.34 g, 28.5 mmol), the compound 6b(8.5 g, 34.3 mmol), and Pd(PPh ) (1.0 g, 0.86 mmol) were added to a 2 M aqueous solution of potassium carbonate (200 mL) and THF (200 mL). The mixture was refluxed under stirring for about 24 hours. After completing the reaction, the mixture was cooled to normal temperature. The organic layer was separated from the reaction mixture, dried over magnesium sulfate, and distilled under reduced pressure. The residue was recrystallized from THF and EtOH to prepare a compound 6c (9.2 g, 85%). MS [M] = 380 [153]
  • 6
  • [ 876442-90-9 ]
  • [ 17135-74-9 ]
  • [ 1220509-65-8 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In tetrahydrofuran; water; at 80℃; (1-3) Synthesis of Intermediate 3; 58 g of <strong>[17135-74-9]1,8-dibromonaphthalene</strong>, 50 g of 6-phenylnaphthalene-2-yl boronic acid, 500 ml of tetrahydrofuran, 42 g of potassium carbonate and 250 ml of water were mixed in a 2000 ml round-bottom flask with stirring. 11.7 g of tetrakis(triphenylphosphine)palladium(0) was added to the mixture, which was heated to 80 C . The organic layer was isolated from the reaction solution, washed twice with water, and dried over magnesium sulfate, which was distilled under a reduced pressure to remove the solvent therefrom. The residue thus obtained was subjected to purification by column chromatography using hexane, to obtain 50 g of the title compound.
  • 7
  • [ 121-43-7 ]
  • [ 22082-94-6 ]
  • [ 876442-90-9 ]
YieldReaction ConditionsOperation in experiment
55% Stage #1: 6-phenyl-2-bromonaphthalene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 2.33333h; Inert atmosphere; Stage #2: Trimethyl borate In tetrahydrofuran; hexane at 20℃; for 20h; Stage #3: With hydrogenchloride In tetrahydrofuran; hexane; water for 0.5h; 4.3.3 Step 3: Synthesis of 6-Phenylnaphthalene-2-boronic acid First, 0.9 g of 2-bromo-6-phenylnaphthalene obtained in the above Step 2 was placed into a 200-mL three-neck flask, and the air in the flask was replaced with nitrogen. To this compound was added 100 mL of tetrahydrofuran (THF), and this solution was stirred at -78° C. for 20 minutes. Then, 2.4 mL of a 1.6M hexane solution of n-butyllithium (n-BuLi) was dripped into this solution, followed by stirring at -78° C. for 2 hours. After the predetermined time had elapsed, 0.8 mL of trimethyl borate was added to the mixture and this solution was stirred for 20 hours while the temperature was raised to room temperature. After the predetermined time had elapsed, 0.60 mL of 1.0M hydrochloric acid was poured into this solution, and the mixture was stirred for 30 minutes. Then, this mixture solution was separated into an organic layer and an aqueous layer. Organic substances were extracted with ethyl acetate from the obtained aqueous layer. The solution of the extract was combined with the organic layer that had been first obtained, and the mixture was washed with saturated brine and dried by addition of anhydrous magnesium sulfate. Then, the filtrate obtained by gravity filtration was concentrated to give a solid. The obtained solid was recrystallized using a mixed solvent of chloroform and hexane, whereby 6-phenylnaphthalene-2-boronic acid was obtained (as a white powder in 55% yield). The synthesis scheme of Step 3 is illustrated in the following (c-4).
  • 8
  • [ 13720-06-4 ]
  • [ 876442-90-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: n-butyllithium / hexane; tetrahydrofuran / 2.33 h / -78 °C / Inert atmosphere 1.2: 18 h / 20 °C 1.3: 1 h 2.1: potassium carbonate / palladium diacetate; tris-(o-tolyl)phosphine / toluene; ethanol; water / 5 h / 85 °C / Inert atmosphere; Reflux 3.1: n-butyllithium / hexane; tetrahydrofuran / 2.33 h / -78 °C / Inert atmosphere 3.2: 20 h / 20 °C 3.3: 0.5 h
  • 9
  • [ 38557-72-1 ]
  • [ 876442-90-9 ]
  • [ 1337916-19-4 ]
YieldReaction ConditionsOperation in experiment
82% With sodium carbonate;bis-triphenylphosphine-palladium(II) chloride; In water; acetonitrile;Inert atmosphere; Microwave irradiation; Step 4: Synthesis of 3,5-Dimethyl-2-(6-phenylnaphthalen-2-yl)pyrazine (abbreviation: Hdm6p2npr)First, into a recovery flask equipped with a reflux pipe were placed 0.24 g of <strong>[38557-72-1]2-chloro-3,5-dimethylpyrazine</strong>, 0.41 g of 6-phenylnaphthalene-2-boronic acid, 0.18 g of sodium carbonate, 0.008 g of bis(triphenylphosphine)palladium(II) dichloride (abbreviation: Pd(PPh3)2Cl2), 10 mL of water, and 10 mL of acetonitrile, and the air in the flask was replaced with argon. This reaction container was irradiated with microwaves (2.45 GHz, 100 W) for 30 minutes, so that heating was performed. Then, the reaction container was cooled to 50 C. or less. Water was added to the reaction solution, and the organic layer was extracted with dichloromethane. The obtained organic layer was washed with water and dried with magnesium sulfate. The solution which had been dried was filtered. The solvent of this solution was distilled, whereby Hdm6p2npr, which is the pyrazine derivative to be produced, was obtained (as a white powder in 82% yield). Note that the microwave irradiation was performed using a microwave synthesis system (Discover, manufactured by CEM Corporation). The synthesis scheme of Step 4 is illustrated in the following (d-4).
  • 10
  • [ 1337916-18-3 ]
  • [ 876442-90-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: potassium carbonate / palladium diacetate; tris-(o-tolyl)phosphine / toluene; ethanol; water / 5 h / 85 °C / Inert atmosphere; Reflux 2.1: n-butyllithium / hexane; tetrahydrofuran / 2.33 h / -78 °C / Inert atmosphere 2.2: 20 h / 20 °C 2.3: 0.5 h
  • 11
  • [ 876442-90-9 ]
  • [ 1344030-91-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: tetrakis(triphenylphosphine) palladium(0) 2.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C 2.2: -78 - 20 °C / Inert atmosphere 3.1: hydrogenchloride / acetic acid; water / 12 h / Reflux 4.1: bromine / tetrachloromethane / 72 h / 20 °C 5.1: tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran / 0.5 h
  • 12
  • [ 876442-90-9 ]
  • 3-bromo-10-phenylspiro[benzo[ij]tetraphene-7,9'-fluorene] [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: tetrakis(triphenylphosphine) palladium(0) 2.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C 2.2: -78 - 20 °C / Inert atmosphere 3.1: hydrogenchloride / acetic acid; water / 12 h / Reflux 4.1: bromine / tetrachloromethane / 72 h / 20 °C
  • 13
  • [ 876442-90-9 ]
  • [ 1344030-88-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: tetrakis(triphenylphosphine) palladium(0) 2.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C 2.2: -78 - 20 °C / Inert atmosphere 3.1: hydrogenchloride / acetic acid; water / 12 h / Reflux 4.1: bromine / tetrachloromethane / 72 h / 20 °C 5.1: tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran / 0.5 h
  • 14
  • [ 876442-90-9 ]
  • [ 1220509-86-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: tetrakis(triphenylphosphine) palladium(0) 2.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C 2.2: -78 - 20 °C / Inert atmosphere 3.1: hydrogenchloride / acetic acid; water / 12 h / Reflux 4.1: bromine / tetrachloromethane / 72 h / 20 °C 5.1: tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran / 0.5 h
  • 15
  • [ 876442-90-9 ]
  • [ 1220509-69-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: tetrakis(triphenylphosphine) palladium(0) 2.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C 2.2: -78 - 20 °C / Inert atmosphere
  • 16
  • [ 876442-90-9 ]
  • [ 1220509-75-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: tetrakis(triphenylphosphine) palladium(0) 2.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C 2.2: -78 - 20 °C / Inert atmosphere 3.1: hydrogenchloride / acetic acid; water / 12 h / Reflux
  • 17
  • [ 876442-90-9 ]
  • 3-bromo-10-(naphthalene-2-yl)spiro[benzo[ij]tetraphene-7,9'-fluorene] [ No CAS ]
  • 3-[2-(6-phenyl)naphthyl]-10-naphthylspiro[benzo[ij]tetraphene-7,9′-fluorene] [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% Stage #1: (6-phenylnaphthalen-2-yl)boronic acid; 3-bromo-10-(naphthalene-2-yl)spiro[benzo[ij]tetraphene-7,9'-fluorene] With tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran for 0.5h; Stage #2: With potassium carbonate In tetrahydrofuran at 80℃;
  • 18
  • [ 876442-90-9 ]
  • C25H16Br2N2 [ No CAS ]
  • C41H28N2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene at 120℃; for 2h; 17 Synthesis Example 17 Intermediate M1 (5.0 g, 10 mmol),6-Phenyl-2-naphthaleneboronic acid (3.0 g, 12 mmol), Pd(PPh3)4 (0.58 g, 0.5 mmol),K2CO3 (5.3 g, 50 mmol), toluene (60 mL),Mix ethanol (20mL) with distilled water (20mL). The reaction was stirred at 120 °C for 2 hours. After the reaction is over,The reaction system was washed with distilled water and extracted with ethyl acetate.The organic layer was separated and the organic layer was dried over MgSO4.Rotary evaporator removes most of the solvent,The residue was separated by silica gel column chromatography (petroleum ether:Ethyl acetate = 50:1 to 10:1),The pale yellow solid A16-1 was obtained.
  • 19
  • [ 876442-90-9 ]
  • [ 624-31-7 ]
  • [ 1247758-32-2 ]
YieldReaction ConditionsOperation in experiment
66% With potassium phosphate In 1,4-dioxane at 115℃; for 24h;
  • 20
  • [ 876442-90-9 ]
  • C35H21BrO [ No CAS ]
  • C51H32O [ No CAS ]
YieldReaction ConditionsOperation in experiment
71% With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; tetrakis(triphenylphosphine) palladium(0) In ethanol; water; toluene at 85℃; for 6h; Inert atmosphere; Synthesis of Compound A69 To the thus obtained intermediate compound C2 (10.8 g, 20 mmol), boric acid, compound D2 (6.3 g, 20 mmol) and K3PO4 (8.5 g, 40 mmol) were added toluene/EtOH/H2O (4/2/1 volume ratio, 250 ml ) And degas. Under an argon atmosphere, add 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (1.6g, 4.0mmol) and tetrakis(triphenylphosphine)palladium (1.6g, 1.0mmol), It was then heated and stirred at about 85°C for about 6 hours. The reaction solution was cooled to room temperature in the air, extracted with toluene, washed with H 2 O and brine, respectively, and dried over Na 2 SO 4. The solution thus obtained was concentrated and separated by silica gel column chromatography to obtain compound A69 (9.9 g, 15 mmol, yield 77%,
  • 21
  • [ 876442-90-9 ]
  • 1-(2-aminophenyl)-2-(tert-butyl)-7-phenyl-3H-benzo[e]indol-3-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: methanol; water 2: nitrosonium tetrafluoroborate / acetonitrile / 0 °C 3: C47H35O4P / ethyl acetate / 24 h / 20 °C / Inert atmosphere
  • 22
  • [ 876442-90-9 ]
  • C27H19NO2 [ No CAS ]
  • C27H19NO2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: methanol; water 2.1: nitrosonium tetrafluoroborate / acetonitrile / 0 °C 3.1: C70H91O4P; di-isopropyl azodicarboxylate / dichloromethane / 0.08 h / Inert atmosphere 3.2: 48 h / -30 °C / Inert atmosphere
  • 23
  • [ 876442-90-9 ]
  • (R)-2-(tert-butyl)-3-(2-nitroso-6-phenylnaphthalen-1-yl)-1H-indole [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: methanol; water 2: nitrosonium tetrafluoroborate / acetonitrile / 0 °C 3: C47H35O4P; 2,5-dibromo-1,4-benzoquinone / dichloromethane / 3 h / 20 °C
  • 24
  • [ 876442-90-9 ]
  • 2-nitroso-6-phenylnaphthalene [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: methanol; water 2: nitrosonium tetrafluoroborate / acetonitrile / 0 °C
  • 25
  • [ 876442-90-9 ]
  • (S)-1-(2-aminophenyl)-2-(tert-butyl)-7-phenyl-3H-benzo[e]indol-3-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: methanol; water 2: nitrosonium tetrafluoroborate / acetonitrile / 0 °C 3: C47H35O4P / ethyl acetate / 24 h / 20 °C / Inert atmosphere
  • 26
  • [ 876442-90-9 ]
  • 2-(tert-butyl)-3-(2-nitroso-6-phenylnaphthalen-1-yl)-1H-indole [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: methanol; water 2: nitrosonium tetrafluoroborate / acetonitrile / 0 °C 3: 2,5-dibromo-1,4-benzoquinone; C47H35O4P / dichloromethane / 3 h / 20 °C
  • 27
  • [ 876442-90-9 ]
  • potassium hydrogen difluoride [ No CAS ]
  • C16H11BF3(1-)*K(1+) [ No CAS ]
YieldReaction ConditionsOperation in experiment
In methanol; water
  • 28
  • [ 876442-90-9 ]
  • [ 13755-29-8 ]
  • [ 69180-49-0 ]
  • (2-methoxyphenyl)(6-phenylnaphthalen-2-yl)iodonium tetrafluoroborate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: (6-phenylnaphthalen-2-yl)boronic acid With boron trifluoride diethyl etherate In dichloromethane at 0℃; for 0.166667h; Stage #2: 1-diacetoxy-2-methoxyphenyl-λ3-iodane In dichloromethane at 20℃; for 2h; Stage #3: sodium tetrafluoroborate In dichloromethane; water for 0.5h;
  • 29
  • [ 876442-90-9 ]
  • benzyl (2'-hydroxy-6'-phenyl-[1,1'-binaphthalen]-2-yl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: boron trifluoride diethyl etherate / dichloromethane / 0.17 h / 0 °C 1.2: 2 h / 20 °C 1.3: 0.5 h 2.1: sodium carbonate / dichloromethane; 2,2,2-trifluoroethanol / 24 h / 20 °C
  • 30
  • [ 876442-90-9 ]
  • benzyl (2'-hydroxy-6,6'-diphenyl-[1,1'-binaphthalen]-2-yl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: boron trifluoride diethyl etherate / dichloromethane / 0.17 h / 0 °C 1.2: 2 h / 20 °C 1.3: 0.5 h 2.1: sodium carbonate / dichloromethane; 2,2,2-trifluoroethanol / 24 h / 20 °C
  • 31
  • [ 876442-90-9 ]
  • benzyl (6-phenyl-2'-((6-phenylnaphthalen-2-yl)oxy)-[1,1'-binaphthalen]-2-yl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: boron trifluoride diethyl etherate / dichloromethane / 0.17 h / 0 °C 1.2: 2 h / 20 °C 1.3: 0.5 h 2.1: caesium carbonate / toluene / 12 h / 20 °C
  • 32
  • [ 876442-90-9 ]
  • C15H9Cl2N3 [ No CAS ]
  • C31H20ClN3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
42% With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In water; toluene at 65℃; Inert atmosphere; 9.2 (2) Synthesis of Intermediate I Intermediate H (4.4 g) and 6-phenyl-2-naphthalenylboronic acid (synthesized according to JP2010-241688A) (4.0 g) were added to toluene (73 mL), and argon gas was passed through the solution for 5 minutes. Dichlorobis(triphenylphosphine)palladium (10 mg) and an aqueous solution of sodium carbonate (2M, 22 mL) was added thereto and heated at 65° C. overnight with stirring under an argon atmosphere. The reaction solution was subjected to column chromatography to obtain Intermediate I (2.9 g, 42% in yield).
  • 33
  • [ 876442-90-9 ]
  • 2,4-dichloro-6-(dibenzo[b,d]furan-3-yl)-1,3,5-triazine [ No CAS ]
  • C31H18ClN3O [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water for 10h; Inert atmosphere; Reflux; 19 Synthesis Example 19 In a nitrogen atmosphere, chemical formula G (15g, 47.4mmol) and sub21 (11.8g, 47.4mmol) were added to 300ml of THF and stirred and refluxed. After that, potassium carbonate (19.7g, 142.3mmol) was dissolved in 59ml of water and stirred sufficiently, and then Tetrakis (triphenylphosphine) palladium (0) (0.5g, 0.5mmol) was added. After 10 hours of reaction, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 17.2 g of subG-3. (Yield 75%,
  • 34
  • [ 876442-90-9 ]
  • 2,4-dichloro-6-(dibenzo[b,d]furan-3-yl)-1,3,5-triazine [ No CAS ]
  • C43H25N3OS [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / tetrahydrofuran; water / 10 h / Inert atmosphere; Reflux 2: potassium carbonate; bis(tri-t-butylphosphine)palladium(0) / tetrahydrofuran; water / 11 h / Inert atmosphere; Reflux
  • 35
  • 4,4,5,5-tetramethyl-2-(2-phenylnaphthyl-6-yl)-1,3,2-dioxaborolane [ No CAS ]
  • [ 876442-90-9 ]
YieldReaction ConditionsOperation in experiment
95% Stage #1: 4,4,5,5-tetramethyl-2-(2-phenylnaphthyl-6-yl)-1,3,2-dioxaborolane With sodium periodate In tetrahydrofuran; water for 0.5h; Stage #2: With hydrogenchloride In tetrahydrofuran; water at 20℃; 9 Synthesis of compound B2 Add compound A2 (584mg, 1.77mmol) and sodium periodate (1.136g, 5.31mmol) into a round bottom flask filled with 12.5mL THF: H2O (4:1, v/v) solvent and stir for 30min.Then HCl solution (1N, 1.24 mL) was added. Stir overnight at room temperature,The reaction was quenched by adding water, extracted with ethyl acetate (40 mL×3),The combined organic layer was washed sequentially with water (20mL×3) and saturated brine (20mL×3),The organic phase is dried and filtered to remove the solvent under reduced pressure. The obtained crude product was purified by column chromatography to obtain compound B2 (417 mg, 95%) as a white solid.
  • 36
  • [ 876442-90-9 ]
  • C24H17NS [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 1-indoline / acetonitrile / 24 h / 20 °C 2: iodine; ammonium thiocyanate / dimethyl sulfoxide / 12 h / 110 °C
  • 37
  • [ 876442-90-9 ]
  • C24H17NO2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 1-indoline / acetonitrile / 24 h / 20 °C 2: iodine; ammonium thiocyanate / dimethyl sulfoxide / 12 h / 110 °C 3: oxygen; methylene blue / dichloromethane / 7 h / 0 °C / Irradiation
  • 38
  • [ 876442-90-9 ]
  • [ 298-12-4 ]
  • C17H12O [ No CAS ]
YieldReaction ConditionsOperation in experiment
With 1-indoline In acetonitrile at 20℃; for 24h; 9 Synthesis of compound C2 Compound B2 (248 mg, 1 mmol) and glyoxylic acid (0.21 mL, 1.05 mmol) were dissolved in 5 mL of acetonitrile, and then 30 mol% indoline (30 μL, 0.3 mmol) was added.Stir at room temperature for 24 hours, the reaction is complete, the solvent is evaporated under reduced pressure,The crude product was purified by column chromatography to obtain compound C2 as a white solid.
  • 39
  • [ 612-94-2 ]
  • [ 876442-90-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: 4,4'-di-tert-butyl-2,2'-bipyridine; (1,5-cyclooctadiene)(methoxy)iridium(l) dimer / cyclohexane / 18 h / 60 °C 2.1: sodium periodate / tetrahydrofuran; water / 0.5 h 2.2: 20 °C
  • 40
  • [ 876442-90-9 ]
  • [ 108-37-2 ]
  • C28H27BO2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: tetrakis-(triphenylphosphine)-palladium; potassium carbonate / toluene; ethanol / 2 h / Inert atmosphere; Reflux 2: palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; anhydrous potassium acetate / N,N-dimethyl-formamide / 5 h / 85 °C / Inert atmosphere
  • 41
  • [ 876442-90-9 ]
  • [ 108-37-2 ]
  • C22H15Cl [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% With tetrakis-(triphenylphosphine)-palladium; potassium carbonate In ethanol; toluene for 2h; Inert atmosphere; Reflux; 1 Preparation of Intermediate 1-1 Under the protection of argon, raw material a-1 (153.00 mmol, 37.96 g), raw material b-1 (150.00 mmol, 28.72 g), Pd(PPh3)4 (3.00 mmol, 3.47 g), K2CO3 were successively added to the reaction flask (300.00 mmol, 41.46 g) and 450 mL of toluene, 150 mL of ethanol,150 mL of water, the mixture was stirred, and the above system was heated under reflux for 2 hours;After the reaction, cooled to room temperature, suction filtered to obtain a filter cake, rinsed with ethanol, and finally recrystallized the filter cake with toluene/ethanol = 4:1 to obtain Intermediate 1-1 (40.61 g, yield 86%)
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