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[ CAS No. 224311-51-7 ] {[proInfo.proName]}

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Chemical Structure| 224311-51-7
Chemical Structure| 224311-51-7
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Product Citations

Product Citations      Expand+

Sims, C.B. ; Chandler, E.T. ; Espitia Armenta, H. , et al. DOI:

Abstract: The development, analysis, characterization, and solvent preference of photo-responsive hybrid 4,4’-divinylazobenzene and octa(dimethylsiloxy)silsesquioxane (Q8M8 H) networks were investigated. The dynamic gel systems are formed through hydrosilylation chemistry and react to visible and UV light to expand and contract, giving them sponge-like properties. Their solvent preference and loading capabilities are analyzed and compared to an analogous system, and general characteristics are illustrated through FTIR, TGA, DMA, and SEM imaging. We find that using a shorter, more rigid azobenzene results in a comparable photo-responsive sponge with a higher initial shrinkage response.

Keywords: 4,4’-Divinylazobenzene ; Photoactuatable ; Smart-gels ; Sponge ; Azobenzene

Purchased from AmBeed:

Cory Blake Sims ;

Abstract: The development of hybrid organosilicon materials as both rapid curing coatings and photo-responsive sponges has been conducted utilizing silsesquioxane (SQ) based chemistries for the robustness they provide in the final materials. Additional research was conducted on the formation of sulfur-based SQ analogs. Chapter I will provide background about the synthesis of silsesquioxanes, their properties, and the favorability for three-dimensional material formation using these molecules. Additional information will include challenges and histories of siloxane based protective coatings and the use of both photo-radical and photo-acid-generating initiators in them, along with a brief explanation of photo-switches, specifically azobenzene and its derivatives and their use in sol-gels. Chapter II will discuss protective coatings for monuments and the specific needs associated with these materials. A history of the types of materials used and their faults will detail the desire for new materials aimed at this application. The development of a coating with three distinct curing methods (including photo-radical and photo-acid generating processes) which forms a protective layer with a mixture of partially formed polisilsesquioxane and oligosilsesquioxane structures as the backbone of the network. Findings and properties of the resulting coating formulations, modifiability, and alternative functionalities will be discussed in detail. Chapter III will discuss the use of photo-switches as crosslinkers in silicon-based networks. Previous work utilized Q-type silsesquioxanes (Q8M8H) and 4,4’-diallyloxyazobenzene (DAA) to develop photodynamic sponges. The modification process of these sponge materials, through both in-situ and post-polymerization functionalization, will be described. The effects on solvent preference resulting from the modifications will describe “sponge” uptake and swell-ability in various environmental pollutants. Chapter IV discusses the synthesis, characterization, and overall performance of an analog Q8M8H sponge system using 4,4’-divinylazobenzne (DVA), in place of 4,4’-diallyloxyazobenzene. Analysis of the resulting changes in swelling efficiency and solvent preference will be provided. Chapter V will describe the investigation into new species of organosilicon compounds. This chapter will detail early work on synthesizing novel silicon-sulfur silsesquioxane analogs, including the methods, challenges, and findings in this underdeveloped field. Chapter VI will provide an overview of the results, findings, and lessons learned through the research above.

Purchased from AmBeed: ;

Product Details of [ 224311-51-7 ]

CAS No. :224311-51-7 MDL No. :MFCD01862440
Formula : C20H27P Boiling Point : -
Linear Structure Formula :C12H9P(C(CH3)3)2 InChI Key :CNXMDTWQWLGCPE-UHFFFAOYSA-N
M.W : 298.40 Pubchem ID :2734215
Synonyms :
Chemical Name :2-(Di-tert-Butylphosphino)biphenyl

Calculated chemistry of [ 224311-51-7 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 21
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.4
Num. rotatable bonds : 4
Num. H-bond acceptors : 0.0
Num. H-bond donors : 0.0
Molar Refractivity : 99.08
TPSA : 13.59 ?2

Pharmacokinetics

GI absorption : Low
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -4.51 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.76
Log Po/w (XLOGP3) : 5.09
Log Po/w (WLOGP) : 6.06
Log Po/w (MLOGP) : 5.86
Log Po/w (SILICOS-IT) : 6.47
Consensus Log Po/w : 5.45

Druglikeness

Lipinski : 1.0
Ghose : None
Veber : 0.0
Egan : 1.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -5.06
Solubility : 0.00263 mg/ml ; 0.0000088 mol/l
Class : Moderately soluble
Log S (Ali) : -5.12
Solubility : 0.00227 mg/ml ; 0.00000761 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -7.43
Solubility : 0.000011 mg/ml ; 0.0000000367 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 3.93

Safety of [ 224311-51-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P501-P273-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313 UN#:N/A
Hazard Statements:H315-H319-H413 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 224311-51-7 ]

* 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 [ 224311-51-7 ]

[ 224311-51-7 ] Synthesis Path-Downstream   1~18

  • 1
  • [ 13716-10-4 ]
  • [ 2052-07-5 ]
  • [ 224311-51-7 ]
YieldReaction ConditionsOperation in experiment
95.7% Under nitrogen protection,1L three bottles,From 40 g of 2-bromobiphenyl,5 g of magnesium turnings and 400 ml of anhydrousTHF to produce Grignard reagent,Refluxed for 2 hours,Down to room temperature,2 g of tetrakis (triphenylphosphine) palladium was added,Stirred for 30 minutes,33 g of di-tert-butylphosphonium chloride was added dropwise at room temperature,The reaction was refluxed for 2 hours.And the mixture was added dropwise to the reaction solution under ice-water bath200 mL of saturated aqueous ammonium chloride was quenched,Liquid separation,The organic phase is dissolved,Add methanol crystallization,Filtration gave 49 g of white 2- (di-tert-butylphosphine) biphenyl, and the yield was 95.7percent.
  • 2
  • [ 622391-65-5 ]
  • [ 224311-51-7 ]
  • [ 622391-71-3 ]
YieldReaction ConditionsOperation in experiment
17% palladium diacetate; In hexane; toluene; Part J. Preparation of 1-cyclopropyl-4-{4-[3-fluoro-4-(4,4,4-trifluoro-butyl)-phenyl]-piperazine-1-sulfonyl}-piperidine-4-carboxylic Acid tert-butyl Ester A mixture of the product of Part I (2.78 g, 6.22 mmol), the product of Part C (1.80 g, 7.48 mmol), palladium(II) acetate (0.070 g, 0.312 mmol), sodium t-butoxide (0.836 g, 8.69 mmol), and 2-(di-t-butylphosphino)biphenyl (0.185, 0.621 mmol) in toluene was heated at 90° C. for 18 hr. The mixture was then diluted with water (350 mL) and extracted with ethyl acetate (3*100 mL). The organic layer was filtered through celite, washed with water (2*100 mL) and brine (100 mL), dried over MgSO4, and concentrated in vacuo to afford a yellow oil. The oil was purified on silica gel (70 g), eluding with 0-100percent ethyl acetate in hexane, to afford 0.638 g (17percent yield) of the desired compound in the form of a yellow oil. MS: m/z=578 (M+H).
  • 3
  • [ 224311-51-7 ]
  • 2-(di(tert-butyl)phosphinyl)biphenyl [ No CAS ]
  • 4
  • [ 224311-51-7 ]
  • [ 719275-59-9 ]
YieldReaction ConditionsOperation in experiment
80% With copper(ll) bromide; In methanol; for 0.25h;Heating / reflux; 50 ml entgastes, wasserfreies Methanol wurde auf Rueckflusstemperatur erhitzt, 2,36 g (7,9 mmol) 2-(Di-tert.-butylphosphino)biphenyl wurde langsam dem Methanol zugegeben, bis die Phosphin-Verbindung vollstaendig geloest war. Anschliessend wurde 0,59 g (2,6 mmol) Kupfer(II)-bromid portionsweise der Loesung zugegeben. Nach Zugabe des Kupferbromids wurde die Loesung noch weitere 15 min lang auf Rueckflusstemperatur erhitzt und danach die Loesung abgekuehlt. Nach Abkuehlen der Loesung fiel ein Feststoff aus, der abfiltriert wurde und mit wenig Ethanol und Diethylether gewaschen und anschliessend getrocknet wurde. Man erhielt 0,93 g (1,1 mmol) der oben genannten Verbindung. Die Ausbeute betrug 80 percent d. Th.
  • 5
  • [ 13716-10-4 ]
  • [ 82214-69-5 ]
  • [ 224311-51-7 ]
YieldReaction ConditionsOperation in experiment
87.5% copper(I) bromide; In tetrahydrofuran; at 30 - 35℃; for 4h;Heating / reflux; In a 500 ml four-necked flask thoroughly purged with nitrogen, 9.0 g (0.05 mol) of di-tert-butylphosphinous chloride, 0.07 g (0.0005 mol (corresponding to 1percent by mol).) of copper(I) bromide and 50 ml of tetrahydrofuran were placed. To the contents of the flask, a Grignard reagent solution previously prepared from 14.0 g (0.060 mol) of 2-bromobiphenyl and 1.7 g (0.072 mol) of metallic magnesium in 100 ml of tetrahydrofuran was dropwise added over a period of 1 hour with maintaining the temperature at 30°C to 35°C. After the dropwise addition was completed, stirring was conducted at a reflux temperature for 4 hours. After the temperature of the reaction solution was returned to room temperature, disappearance of di-tert-butylphosphinous chloride was confirmed by gas chromatography. Thereafter, 30 ml of toluene and 30 ml of a 5percent sulfuric acid aqueous solution were added to the reaction solution to perform liquid separation. Then, the organic layer was washed with water and dried over anhydrous sodium sulfate. The solvent and a low-boiling component were distilled off under reduced pressure to obtain coarse crystals. The coarse crystals were recrystallized from MeOH to obtain 13.2 g (purity: 99.0percent) of the aimed di-tert-butyl(2-phenylphenyl)phosphine. The yield was 87.5percent. Melting point: 84-85°C
  • 6
  • [ 473416-06-7 ]
  • [ 224311-51-7 ]
  • [ 395101-91-4 ]
YieldReaction ConditionsOperation in experiment
To a solution of 600 mg of tert-butyl 3-bromo-5-cyano-1H-1-indazolecarboxylate produced in Production Example I-14-b in 9 ml tetrahydrofuran were added 21 mg of palladium(II) acetate, 57 mg of 2-(di-tert-butylphosphino)biphenyl, 357 mg of potassium fluoride and 498 mg of 2-benzo[b]thiopheneboronic acid, and the mixture was stirred at 50C for 1 hour. After removing the solvent by distillation, the residue was dissolved in 2 ml of methylene chloride. 4 ml of trifluoroacetic acid was added and the mixture was stirred at room temperature for one day. After removing the solvent by distillation, the residue was diluted with 50 ml of ethyl acetate. The mixture was sequentially washed with saturated aqueous sodium hydrogencarbonate solution and brine, dried over anhydrous magnesium sulfate and the solvent was evaporated. The crude product was purified and separated by silica gel column chromatography (ethyl acetate:toluene = 1:19), to give 294 mg of the title compound as bright yellow crystals.1H-NMR (400 MHz, DMSO-D6) d 7.41 (2H, t, J = 7.8 Hz), 7.44 (2H, t, J = 7.8 Hz), 7.80 (2H, s), 7.91 (1H, d, J = 8.0 Hz), 8.01 (1H, d, J = 8.0 Hz), 8.41 (1H, s), 8.99 (1H, s), 13.88 (1H, s).
  • 7
  • [ 699014-97-6 ]
  • [ 224311-51-7 ]
  • [ 699014-98-7 ]
YieldReaction ConditionsOperation in experiment
With potassium phosphate;palladium diacetate; In toluene; at 100℃; for 10h; Under nitrogen atmosphere, a mixture of 4-[[4-[2-[(tert-butoxycarbonyl)[(2R)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]ethyl]phenyl]sulfonyl]phenyl trifluoromethanesulfonate (265 mg), palladium(II)acetate (5 mg), 2-[bis(tert-butyl)phosphino]biphenyl (12 mg), and powdered potassium phosphate (177 mg) in toluene (2.6 ml) was heated to 100° C. for 10 hours.After being allowed to cool to room temperature, the mixture was concentrated and the residue was purified by column chromatography (silica gel, hexane/ethyl acetate) to give ethyl 4-[4-[[4-[2-[(tert-butoxycarbonyl)[(2R)-2-(3-chlorophenyl)-2-hydroxyethyl]-amino]ethyl]phenyl]sulfonyl]phenoxy]benzoate (93 mg) as a white amorphous. NMR (CDCl3, delta): 1.36 (9H, br s), 1.40 (3H, t, J=7 Hz), 2.60-3.05 (2H, m), 3.05-3.60 (4H, m), 4.27 (1H, br s, OH), 4.38 (2H, q, J=7 Hz), 4.86 (1H, m), 6.90-7.45 (10H, m), 7.86 (2H, d, J=8 Hz), 7.90 (2H, d, J=8 Hz), 8.07 (2H, d, J=8 Hz) (+)ESI-MS (m/z): 702 (M+Na)+
  • 8
  • [ 7789-45-9 ]
  • [ 224311-51-7 ]
  • bis(2-(di-tert-butylphosphino)biphenylcopper(I) bromide) [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% In methanol; for 0.25h;Heating / reflux; 50 ml of degassed, anhydrous methanol were heated to reflux temperature, and 2.36 g (7.9 mmol) of 2-(di-tert-butylphosphino)biphenyl were added slowly to the methanol until the phosphine compound was completely dissolved. Subsequently, 0.59 g (2.6 mmol) of copper(II) bromide was added to the solution in portions. After the copper bromide had been added, the solution was heated to reflux temperature for a further 15 min, and then the solution was cooled. After the solution had been cooled, a solid precipitated out and was filtered off, and was washed with a little ethanol and diethyl ether and subsequently dried. 0.93 g (1.1 mmol) of the abovementioned compound was obtained. The yield was 80percent of theory.
  • 9
  • potassium phosphate [ No CAS ]
  • [ 548465-63-0 ]
  • [ 98-17-9 ]
  • [ 224311-51-7 ]
  • [ 548465-92-5 ]
YieldReaction ConditionsOperation in experiment
palladium diacetate; In water; ethyl acetate; toluene; Example 9 A mixture of 5-(3-bromophenoxy)isophthalonitrile (75 mg), 3-hydroxybenzotrifluoride (61 mg), palladium(II) acetate (11 mg), tripotassium phosphate (0.106 g) and 2-(di-tert-butylphosphino)biphenyl (18 mg) in dry toluene was heated at reflux under a nitrogen atmosphere for 24 hours. Water and ethyl acetate were added to the cooled mixture, followed by acidification with aqueous hydrochloric acid (2M). The phases were separated and the organic layer dried over magnesium sulphate, concentrated and purified by flash chromatography. Elution with 5percent ethyl acetate/i-hexane gave 5-[3-(3-trifluoromethylphenoxy)phenoxy]isophthalonitrile (Compound 77, 32 mg), NMR 7.62 (1H, s); 7.52-7.37 (5H, m); 7.31 (1H, s); 7.25 (1H, d); 6.92 (1H, dd); 6.82 (1H, dd); 6.73 (1H, t).
  • 10
  • tris(dibenzylideneacetone)dipalladium (0) [ No CAS ]
  • [ 136030-00-7 ]
  • [ 67714-53-8 ]
  • [ 224311-51-7 ]
  • [ 865-48-5 ]
  • [ 535934-27-1 ]
YieldReaction ConditionsOperation in experiment
184 mg (65%) With sodium hydrogencarbonate; In water; ethyl acetate; toluene; Preparation 1 (1R,2S)-1-[(3,6-diethylpyrazin-2-yl)amino]-2,3-dihydro-1H-inden-2-ol A solution of 3-chloro-2,5-diethylpyrazine (171 mg, 1.0 mmol), (1R,2S)-(+)-cis-1-amino-2-indanol (298 mg, 2.0 mmol), tris(dibenzylideneacetone)dipalladium (0) (28 mg, 0.03 mmol), and 2-(di-tertbutylphosphino)biphenyl (18 mg, 0.06 mmol) in toluene (2.0 mL) was purged with nitrogen and treated with sodium tertbutoxide (135 mg, 1.4 mmol). The resulting brown suspension was heated to 100° C. for 2 hours. At this time, the reaction was quenched with a saturated water solution of NaHCO3 and extracted twice with ethyl acetate (20 mL). The combined organics were washed with brine (15 mL), dried over MgSO4, filtered, and concentrated to give a black solid. This material was purified by biotage MPLC (40 g column, 25percent ethyl acetate/heptane) to afford 184 mg (65percent) of the title compound as a light purple solid. IR (diffuse reflectance) 3435, 3241, 2962, 2935, 2912, 2873, 1581, 1547, 1500, 1453, 1184, 1163, 1047, 744, 733 cm-1; OAMS supporting ions at: ESI+384.0; MS (CI) m/z 284 (MH+); HRMS (FAB) calcd for C17H21N3O +H1 284.1763, found 284.1754. [alpha]25D=12 (c 0.55, methylene chloride); Anal. Calcd for C17H21N3O: C, 72.06; H, 7.47; N, 14.83. Found: C, 72.15; H, 7.53; N, 14.42.
  • 11
  • [ 625-92-3 ]
  • [ 224311-51-7 ]
  • [ 57260-71-6 ]
  • [ 412348-60-8 ]
YieldReaction ConditionsOperation in experiment
20% tris-(dibenzylideneacetone)dipalladium(0); In 1,4-dioxane; ethyl acetate; Example 123A 4-(5-Bromo-pyridin-3-yl)-piperazine-1-carboxylic Acid Tert-Butyl Ester A solution of the 3,5-dibromo-pyridine (12.8 g, 68.8 mmol) and piperazine-1-carboxylic acid tert butyl ester (10 g, 42.4 mmol) in 200 mL of dioxane was treated with Pd2(dba)3 (5 g, 5.5 mmol), 2-(di-tbutyl-phosphino)biphenyl (4 g, 13.4 mmol), and sodium t-butoxide (7.2 g, 75 mmol). The reaction was heated to 95° C. for 8 h then cooled and filtered through celite. The mixture was evaporated and the residue was purified by flash column chromatography on silica gel, eluding with a solvent gradient of 1:4 ethyl acetate/hexane to 100percent ethyl acetate. Recovered 2.9 g of product (20percent). MS (ESI) m/z 344 (M+H)+.
  • 12
  • acetone-CH2Cl2 [ No CAS ]
  • Zn(CN)2 [ No CAS ]
  • [ 569359-54-2 ]
  • ethyl acetate n-hexane [ No CAS ]
  • [ 224311-51-7 ]
  • [ 569680-08-6 ]
YieldReaction ConditionsOperation in experiment
26% tris-(dibenzylideneacetone)dipalladium(0); EXAMPLE 2 10-Butyl-8-cyano-10-(trifluoromethyl)-5,10-dihydropyrimido[5,4-b]quinolin-4(3H)-one (9): 10-Butyl-8-chloro-10-(trifluoromethyl)-5,10-dihydropyrimido[5,4-b]quinolin-4(3H)-one (8, 34 mg, 0.095 mmol) was dissolved in NMP (0.5 mL, 0.2M). Zn (7.4 mg, 0.114 mmol, 1.2 equiv), Zn(CN)2 (6.7 mg, 0.057 mmol, 0.6 equiv) and 2-(di-t-butylphosphino)biphenyl (23 mg, 0.076 mmol, 0.8 equiv) were added and the solution was degassed with a stream of nitrogen. Pd2(dba)3 (17 mg, 0.019 mmol, 0.2 equiv) was added and the reaction was degassed a second time before heating to 150° C. After 16 hours, the reaction was complete by TLC. The reaction was cooled to rt and diluted with EtOAc (0.7 mL). The organic phase was washed with 2N aq. NH4OH solution, brine and then concentrated with a stream of N2. Chromatography (SiO2, 15percent acetone-CH2Cl2, then 50percent EtOAc-hexane) provided the desired material as a beige solid (8.7 mg, 26percent). Rf 0.27 (50percent Ethyl acetate-hexane). 1H NMR (CDCl3, 300 MHz) 610.53 (br s, NH), 7.87 (s, 1H), 7.69 (s, 1H), 7.54 (d, J=8.5 Hz, 1H), 6.94 (d, J=8.5 Hz, 1H), 2.86 (m, 1H), 1.39 (m, 2H), 0.99 (m, 2H), 0.86 (t, J=7.3 Hz, 3H). 19F NMR (CDCl3, 300 MHz) delta-75.62; ESI-HRMS 349.1295 (M++H, C17H15F3N4O requires 349.1276).
  • 13
  • [ 374554-85-5 ]
  • [ 374554-84-4 ]
  • [ 224311-51-7 ]
  • [ 374556-18-0 ]
YieldReaction ConditionsOperation in experiment
6.4% With sodium t-butanolate;tris-(dibenzylideneacetone)dipalladium(0); In dichloromethane; toluene; EXAMPLE 85 A suspension of 1-bromo-3-(1,2-dimethylimidazol-5-yl)benzene (116 mg), 4,5-dihydro[1]benzoxepino[5,4-c]isoxazol-3-amine (112 mg), sodium tert-butoxide (62 mg), biphenyl-2-yl-di-tert-butylphosphine (11 mg) and tris(dibenzylideneacetone)dipalladium (8 mg) in toluene (1 ml) was stirred for 12 hours at ambient temperature and for an hour at 60° C. The mixture was diluted with ethyl acetate and washed with water and brine. The organic layer was separated, dried over magnesium sulfate and evaporated. The residue was purified by a column chromatography on silica gel eluding with 3percent methanol in dichloromethane to give N-[3-(1,2-dimethyl-1H-imidazol-5-yl)phenyl]-4,5-dihydro[1]benzoxepino[5,4-c]isoxazol-3-amine (11 mg, 6.4percent). APCI-MASS: 373 (m/z, (M+H)+) NMR(DMSO-d6, delta): 2.35 (3H, s), 2.85 (2H, t, J=5.1 Hz), 3.55 (1H, s), 4.30 (2H, t, J=5.1 Hz), 6.55 (1H, s), 6.86 (1H, s), 7.0-7.3 (4H, m), 7.3-7.5 (2H, m), 8.10 (1H, dd, J=1.6 Hz, 7.9 Hz), 9.47 (1H, s).
  • 14
  • [ 475160-93-1 ]
  • [ 87199-17-5 ]
  • [ 224311-51-7 ]
  • [ 475160-94-2 ]
YieldReaction ConditionsOperation in experiment
63% With KF;palladium diacetate; In tetrahydrofuran; (4'-Formylbiphenyl-2-ylmethyl)-carbamic acid 9H-fluoren-9-ylmethyl ester (S29). 4-Formylphenylboronic acid (4.97 g, 33.2 mmol), aryl bromide S28 (9.0 g, 22 mmol), KF (3.8 g, 66 mmol), <strong>[224311-51-7]biphenyl-2-yl-di-tert-butyl-phosphane</strong> (0.26 g, 0.884 mmol), and palladium(II) acetate (0.099 g, 0.44 mmol) were charged into an oven-dried flask. After one evacuation/backfill cycle with Ar, the solids were dissolved in THF (45 mL) and heated moderately (30° C.) with stirring. After 24 h, the reaction was diluted with CH2Cl2 and was washed with 1 M NaOH. The aqueous layer was extracted with CH2Cl2 and the combined organics were then washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. The crude solid was purified by flash column chromatography (silica gel, 30percent ethyl acetate/hexanes) to obtain a white solid (6.0 g, 63percent). 1H NMR (400 MHz, d6-DMSO): delta10.04 (s, 1H), 7.95 (d, 2H, J=8.2 Hz), 7.88 (d, 2H, J=7.5 Hz), 7.82 (t, 1H, J=5.9 Hz, NH), 7.67 (d, 2H, J=7.5 Hz), 7.59 (d, 2H, J=8.2 Hz), 7.43-7.30 (m, 7H), 7.24 (d, 1H, J=7.7 Hz), 4.29 (d, 2H, J=7.0 Hz), 4.19 (t, 1H, J=7.0 Hz), 4.12 (d, 2H, J=5.9 Hz). APCI/MS: 434 (M+H+).
63% With KF;palladium diacetate; In tetrahydrofuran; (4'-Formylbiphenyl-2-ylmethyl)-carbamic acid 9H-fluoren-9-ylmethyl ester (S29). 4-Formylphenylboronic acid (4.97 g, 33.2 mmol), aryl bromide S28 (9.0 g, 22 mmol), KF (3.8 g, 66 mmol), <strong>[224311-51-7]biphenyl-2-yl-di-tert-butyl-phosphane</strong> (0.26 g, 0.884 mmol), and palladium(II) acetate (0.099 g, 0.44 mmol) were charged into an oven-dried flask. After one evacuation/backfill cycle with Ar, the solids were dissolved in THF (45 mL) and heated moderately (30° C.) with stirring. After 24 h, the reaction was diluted with CH2Cl2 and was washed with 1 M NaOH. The aqueous layer was extracted with CH2Cl2 and the combined organics were then washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. The crude solid was purified by flash column chromatography (silica gel, 30percent ethyl acetate/hexanes) to obtain a white solid (6.0 g, 63percent). 1H NMR (400 MHz, d6-DMSO): delta10.04 (s, 1H), 7.95 (d, 2H, J=8.2 Hz), 7.88 (d, 2H, J=7.5 Hz), 7.82 (t, 1H, J=5.9 Hz, NH), 7.67 (d, 2H, J=7.5 Hz), 7.59 (d, 2H, J=8.2 Hz), 7.43-7.30 (m, 7H), 7.24 (d, 1H, J=7.7 Hz), 4.29 (d, 2H, J=7.0 Hz), 4.19 (t, 1H, J=7.0 Hz), 4.12 (d, 2H, J=5.9 Hz). APCI/MS: 434 (M+H+).
  • 15
  • [ 87199-17-5 ]
  • [ 224311-51-7 ]
  • [ 475160-92-0 ]
  • [ 475160-95-3 ]
  • [ 475160-94-2 ]
YieldReaction ConditionsOperation in experiment
60% With KF;palladium diacetate; In tetrahydrofuran; (4'-Formylbiphenyl-3-ylmethyl)-carbamic acid 9H-fluoren-9-ylmethyl ester (S30). 4-Formylphenylboronic acid (5.0 g, 33 mmol), aryl bromide S27 (9.0 g, 22 mmol), KF (3.8 g, 66 mmol), <strong>[224311-51-7]biphenyl-2-yl-di-tert-butyl-phosphane</strong> (0.26 g, 0.88 mmol), and palladium(II) acetate (0.099 g, 0.44 mmol) were charged into an oven-dried flask. After one evacuation/backfill cycle with Ar, the solids were dissolved in THF (45 mL) and heated to reflux with stirring. After 5 h, the reaction was diluted with ethyl acetate, filtered through a celite pad and washed with 1 M NaOH. The aqueous layer was extracted with ethyl acetate and the combined organics were then washed with brine, dried over MgSO4, filtered, and concentrated in vacuo to afford an orange oil (13 g). The crude oil was purified by flash column chromatography (silica gel, 30percent ethyl acetate/hexanes) to obtain aldehyde S29 as a yellow oil (5.7 g, 60percent). 1H NMR (400 MHz, CDCl3): delta10.06 (s, 1H), 7.95 (d, 2H, J=8.2 Hz), 7.76 (d, 2H, J=7.5 Hz), 7.74 (d, 2H, J=8.2 Hz), 7.59 (d, 2H, J=7.5 Hz), 7.56 (m, 1H), 7.55 (s, 1H), 7.46 (dd, 1H, J=7.9 Hz, 7.9 Hz), 7.39 (dd, 2H, J=7.5 Hz, 7.5 Hz), 7.33 (m, 1H), 7.29 (dd, 2H, J=7.5 Hz, 7.5 Hz), 5.16 (broad s, 1H), 4.48 (d, 2H, J=7.0 Hz), 4.47 (s, 2H), 4.24 (t, 1H, J=7.0 Hz). ESI/MS: 456 (M+Na+).
60% With KF;palladium diacetate; In tetrahydrofuran; (4'-Formylbiphenyl-3-ylmethyl)-carbamic acid 9H-fluoren-9-ylmethyl ester (S30). 4-Formylphenylboronic acid (5.0 g, 33 mmol), aryl bromide S27 (9.0 g, 22 mmol), KF (3.8 g, 66 mmol), <strong>[224311-51-7]biphenyl-2-yl-di-tert-butyl-phosphane</strong> (0.26 g, 0.88 mmol), and palladium(II) acetate (0.099 g, 0.44 mmol) were charged into an oven-dried flask. After one evacuation/backfill cycle with Ar, the solids were dissolved in THF (45 mL) and heated to reflux with stirring. After 5 h, the reaction was diluted with ethyl acetate, filtered through a celite pad and washed with 1 M NaOH. The aqueous layer was extracted with ethyl acetate and the combined organics were then washed with brine, dried over MgSO4, filtered, and concentrated in vacuo to afford an orange oil (13 g). The crude oil was purified by flash column chromatography (silica gel, 30percent ethyl acetate/hexanes) to obtain aldehyde S29 as a yellow oil (5.7 g, 60percent). 1H NMR (400 MHz, CDCl3): delta10.06 (s, 1H), 7.95 (d, 2H, J=8.2 Hz), 7.76 (d, 2H, J=7.5 Hz), 7.74 (d, 2H, J=8.2 Hz), 7.59 (d, 2H, J=7.5 Hz), 7.56 (m, 1H), 7.55 (s, 1H), 7.46 (dd, 1H, J=7.9 Hz, 7.9 Hz), 7.39 (dd, 2H, J=7.5 Hz, 7.5 Hz), 7.33 (m, 1H), 7.29 (dd, 2H, J=7.5 Hz, 7.5 Hz), 5.16 (broad s, 1H), 4.48 (d, 2H, J=7.0 Hz), 4.47 (s, 2H), 4.24 (t, 1H, J=7.0 Hz). ESI/MS: 456 (M+Na+).
  • 16
  • [ 109-01-3 ]
  • (3-Trifluoromethanesulfonyloxy-5,6,7,8-tetrahydro-naphthalen-1-yl)-acetic acid ethyl ester [ No CAS ]
  • tris(dibenzylideneacetoneacetone)-dipalladium(0) [ No CAS ]
  • [ 224311-51-7 ]
  • [ 425638-72-8 ]
YieldReaction ConditionsOperation in experiment
With potassium phosphate; In tetrahydrofuran; e [3-(4-Methyl-piperazin-1-yl)-5,6,7,8-tetrahydro-naphthalen-1-yl]-acetic Acid Ethyl Ester To a solution of compound of step d) (0.5 g, 1.36 mmol) in dry THF (10 ml) K3PO4 (405 mg, 1.90 mmol), N-methylpiperazine (180 mul, 163 mmol), tris(dibenzylideneacetoneacetone)-dipalladium(0) (60 mg, 0.07 mmol) and 2-(di-t-butylphosphino)biphenyl (21 mg, 0.07 mmol) are added under argon. The reaction is kept under argon at 80° C. for 24 hours. After filtration DMF is removed under reduced pressure and the crude residue is purified on silica gel (methylene chloride/methanol 95/5) affording the pure compound. 1H NMR (400 MHz, CDCl3) delta 6.68 (d, 1H, J=2.44 Hz), 6.59 (d, 1H, J=2.20 Hz), 4.15 (q, 2H, J=7.34 Hz), 3.55 (s, 2H), 3.17 (t, 4H, J=5.13 Hz), 2.75 (t, 2H, J=5.87 Hz), 2.60 (t, 2H, J=6.11 Hz), 2.57 (t, 4H, J=4.90 Hz), 2.35 (s, 3H), 1.77 (m, 4H), 1.25 (t, 3H, J=7.10 Hz)
  • 17
  • [ 50488-36-3 ]
  • (CO2H)2 [ No CAS ]
  • [ 477601-25-5 ]
  • [ 108-88-3 ]
  • [ 224311-51-7 ]
  • [ 477601-08-4 ]
YieldReaction ConditionsOperation in experiment
23% With ammonia;tris-(dibenzylideneacetone)dipalladium(0); In methanol; ethanol; water; ethyl acetate; Step 6 6-Methoxy-N-{2-[3-(2-naphthyl)-8-azabicyclo[3.2.1]oct-2-en-8-yl]ethyl}-8-quinolinamine A mixture of 0.17 g, (0.61 mmol) 2-[3-(2-naphthyl)-8-azabicyclo[3.2.1]oct-2-en-8-yl]ethylamine, 0.13 g (0.55 mmol) 8-bromo-6-methoxyquinoline, 30 mg (0.03 mmol) Pd2(dba)3, 20 mg (0.08 mmol) 2-(di-t-butylphosphino)biphenyl and 10 mL PhMe is stirred at 23° C. for 16 h. The reaction mixture is poured into 100 mL of H2O and extracted 3*50 mL EtOAc. The combined organics are washed with 1*100 mL H2O, 1*100 mL brine, dried over MgSO4, filtered, and the volatiles are evaporated. The crude product is subjected to flash chromatography on SiO2, eluding with EtOAc to EtOAc/2M NH3 in MeOH (40/1), to give the title compound as an off-white solid. This solid is dissolved in 4 mL of absolute EtOH and treated with 0.01 g (0.14 mmol) (CO2H)2 to give 0.07 g (0.13 mmol, a 23percent yield) of the oxalate salt of the title compound as a dark green solid: mp: 179-182 C; MS (ES) m/z 436 (MH)+.
  • 18
  • [ 110-89-4 ]
  • tripotassium phosphate (K3PO4) [ No CAS ]
  • [ 109586-45-0 ]
  • [ 224311-51-7 ]
  • 5-hydroxy-2-phenyl-7-piperidin-1-yl-chromen-4-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
18 mg (17%) tris-(dibenzylideneacetone)dipalladium(0); In tetrahydrofuran; EXAMPLE 140 5-Hydroxy-2-phenyl-7-piperidin-1-yl-chromen-4-one A solution of trifluoromethanesulfonic acid 5-hydroxy-4-oxo-2-phenyl-4H-chromen-7-yl ester (130 mg, 0.337 mmol), piperidine (0.040 mL, 0.40 mmol), tris(dibenzylideneacetone)dipalladium(0) (15 mg, 0.017 mmol), <strong>[224311-51-7]biphenyl-2-yl-di-tert-butyl-phosphane</strong> (20 mg, 0.067 mmol), and tripotassium phosphate (K3PO4) (143 mg, 0.674 mmol) in THF (2 mL) was heated to reflux for 24 h, then cooled to room temperature for 24 h. The reaction mixture was filtered through a 3/4" silica gel (60 A) plug. The plug was washed with EtOAc (75 mL), and the filtrate concentrated. The concentrate was purified via Biotage chromatography eluding with 5percent EtOAc/hexanes to yield 18 mg (17percent) of 5-hydroxy-2-phenyl-7-piperidin-1-yl-chromen-4-one. 1H NMR (CDCl3, 400 MHz) delta12.6 (s, 1H), 7.87 (m, 2H), 7.52-7.49 (c, 3H), 6.59 (m, 1H), 6.36 (m, 1H), 6.28 (m, 1H), 3.41 (br s, 4H), 1.68 (br s, 6H). LRMS (Electrospray, positive): Da/e 322.5 (m+1).
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