*Storage: {[sel_prStorage]}
*Shipping: {[sel_prShipping]}
The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
Bis(pinacolato)diborane is used as a biomaterial or organic compound in life science-related research.
4.5
*For Research Use Only !
Change View
Size | Price | VIP Price | US Stock |
Global Stock |
In Stock | ||
{[ item.pr_size ]} |
Inquiry
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,1,item.pr_is_large_size_no_price, item.discount_usd) ]} {[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]} |
Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]} | Inquiry {[ item.pr_usastock ]} In Stock Inquiry - | {[ item.pr_chinastock ]} {[ item.pr_remark ]} In Stock 1-2 weeks - Inquiry - | Login | - + | Inquiry |
Please Login or Create an Account to: See VIP prices and availability
US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days
1-2weeks
Inquiry
{[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]}
{[ getRatePrice(item.pr_usd,1,item.mem_rate,item.pr_is_large_size_no_price, item.pr_usd) ]}
Inquiry
{[ getRatePrice(item.pr_usd,item.pr_rate,1,item.pr_is_large_size_no_price, item.vip_usd) ]}
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]}
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]}
In Stock
- +
Please Login or Create an Account to: See VIP prices and availability
US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Catalytic asymmetric synthesis of meta benzene isosteres
Zhang, Mingkai ; Chapman, Matthew ; Sarode, Bhagyesh R ; Xiong, Bingcong ; Liang, Hao ; Chen, James K , et al.
Abstract: Although aromatic rings are common elements in pharmaceutically active compounds, the presence of these motifs brings several liabilities with respect to the developability of a drug1. Nonoptimal potency, metabolic stability, solubility and lipophilicity in pharmaceutical compounds can be improved by replacing aromatic rings with non-aromatic isosteric motifs2. Moreover, whereas aromatic rings are planar and lack three-dimensionality, the binding pockets of most pharmaceutical targets are chiral. Thus, the stereochemical confguration of the isosteric replacements may ofer an added opportunity to improve the afnity of derived ligands for target receptors. A notable impediment to this approach is the lack of simple and scalable catalytic enantioselective syntheses of candidate isosteres from readily available precursors. Here we present a previously unknown palladium-catalysed reaction that converts hydrocarbon-derived precursors to chiral boron-containing nortricyclanes and we show that the shape of these nortricyclanes makes them plausible isosteres for metadisubstituted aromatic rings. With chiral catalysts, the Pd-catalysed reaction can be accomplished in an enantioselective fashion and subsequent transformation of the boron group provides access to a broad array of structures. We also show that the incorporation of nortricyclanes into pharmaceutical motifs can result in improved biophysical properties along with stereochemistry-dependent activity. We anticipate that these features, coupled with the simple, inexpensive synthesis of the functionalized nortricyclane scafold, will render this platform a useful foundation for the assembly of new biologically active agents.
Show More >
Synthetic Elaboration of β-Carbonyl Alkylboronic Esters
Hamilton, Mason D ;
Abstract: Organoboron compounds are some of the most synthetically versatile compounds in organic chemistry due to the many valuable transformations of the C-B bond. This synthetic versatility combined with the pharmacophoric nature of carboxylic acids has led to an increased interest in the one-pot difunctionalization of vinyl arenes using CO2 and pinacol boranes. Recently, much progress has been made to improve the scope and versatility of boracarboxylation reactions to now include electron-deficient and α-methyl substituted vinyl arenes. However, the potential transformations of boracarboxylated products have remained unexplored. Here, methodologies to transform the β-aryl alkylboronic ester into new C-C, C-N, and C-X bonds will be described. Medically relevant 2,3-diarylpropionic acids can now be accessed via a two-step protocol consisting of boracarboxylation of a vinyl arene followed by a palladium(0)-catalyzed Suzuki cross-coupling. This methodology provides access to both the α- and β-regioisomers independently whereas traditional strategies to access these compounds afford only one regioisomer, and in most cases, a mixture of regioisomers. Interesting biaryl and heterocyclic products can be accessed and to demonstrate the synthetic utility of this protocol, a glucagon receptor antagonist was synthesized in 4 less steps than the previously reported method while maintaining similar yields. The transformative capability of boracarboxylated products is further demonstrated through a base-_x005f_x0002_and external oxidant-free copper(II)-catalyzed amination to generate β2-amino acid derivatives. While the β-carboxylic acid was intolerable to the conditions, protection via esterification or amidation allowed for successful amination of the alkylboronic ester to occur. Amination of two bora-NSAIDs, bora-ibuprofen and bora-naproxen, was successful and a number of cyclic and acyclic amines are suitable for the transformation. Preliminary mechanistic work suggests that this amination does not proceed through a free-radical intermediate but rather a two-electron pathway. Finally, a novel halogenation of boracarboxylated products is achieved to generate the corresponding β-aryl alkyl halides. This methodology is performed in a base, metal, and additive free manner that utilizes cheap and readily available sources of electrophilic halide. Both bromination and iodination are demonstrated and can be achieved on a variety of electron-rich and electron-poor boracarboxylated products and can subsequently undergo amination to provide an alternative route to β2-amino acid derivatives. Mechanistic experiments suggest that the β-carboxylic acid is required to achieve the activation of the C-B bond. Radical trapping experiments also indicate that this transformation may occur through the formation of an alkyl radical although this is unlikely.
Show More >
Keywords: Boracarboxylation ; alkylboronic ester ; Suzuki cross-coupling ; oxidative amination ; 2,3-diarylpropionic acid ; β2-amino acid
Show More >
PROTACs Targeting MLKL Protect Cells from Necroptosis
Rathje, Oliver H. ; Perryman, Lara ; Payne, Richard J. ; Hamprecht, Dieter W. ;
Abstract: Mixed Lineage Kinase domain-Like pseudokinase (MLKL) is implicated in a broad range of diseases due to its role as the ultimate effector of necroptosis and has therefore emerged as an attractive drug target. Here, we describe the development of PROteolysis TArgeting Chimeras (PROTACs) as a novel approach to knock down MLKL through chem. means. A series of candidate degraders were synthesized from a high-affinity pyrazole carboxamide-based MLKL ligand leading to the identification of a PROTAC mol. that effectively degraded MLKL and completely abrogated cell death in a TSZ model of necroptosis. By leveraging the innate ability of these PROTACs to degrade MLKL in a dose-dependent manner, the quant. relationship between MLKL levels and necroptosis was interrogated. This work demonstrates the feasibility of targeting MLKL using a PROTAC approach and provides a powerful tool to further our understanding of the role of MLKL within the necroptotic pathway.
Show More >
Purchased from AmBeed: 30100-16-4 ; 4530-20-5 ; 1703808-53-0 ; 2840-26-8 ; 234081-98-2 ; 108466-89-3 ; 1005342-46-0 ; 154775-43-6 ; 214360-73-3 ; 31108-57-3 ; 57294-38-9 ; 234081-98-2 ; 73183-34-3 ; 462100-06-7 ; 187389-52-2 ; 191732-72-6 ; 173405-78-2 ; 154590-35-9 ; 6404-29-1 ; 1807518-63-3 ; 62595-74-8 ; 77383-17-6 ; 1310949-97-3 ; 138563-69-6 ; 138563-68-5 ; 2704620-74-4 ; 2284453-73-0 ; 191732-72-6 ; 181073-79-0
Show More >
CAS No. : | 73183-34-3 |
Formula : | C12H24B2O4 |
M.W : | 253.94 |
SMILES Code : | CC1(C)C(C)(C)OB(B2OC(C)(C)C(C)(C)O2)O1 |
MDL No. : | MFCD00799570 |
InChI Key : | IPWKHHSGDUIRAH-UHFFFAOYSA-N |
Pubchem ID : | 2733548 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P264-P271-P280-P302+P352-P305+P351+P338 |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45% | With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 4,4'-di-tert-butyl-2,2'-bipyridine In hexane at 20℃; for 16 h; | Example 2 illustrates the sp2-carbon borylation and hydrogenation of a furan substrate to form a corresponding 2-substituted sp3-carbon borylated tetrahydrofuran. Scheme 12 illustrates sp2-carbon borylation of furan with an iridium-based catalyst ([IrOMe(cod)]2 and dtbpy) in hexane (rt for 16 h). The sp2-carbon borylated product is hydrogenated using hydrogen with a rhodium-based catalyst (Rh/Al2O3) in ethanol (rt for 15 h) to form the corresponding hydrogenated, 2-substituted sp3-carbon borylated tetrahydrofuran product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With (2,2,2-trifluoroethoxy)trimethylsilane; cesium fluoride; dichlorobis(trimethylphosphine)nickel In 1,4-dioxane at 100℃; for 12 h; Inert atmosphere; Sealed tube | Under an argon atmosphere,To the reaction vessel, 1.4 mg (0.005 mmol) of dichlorobis (trimethylphosphine) nickel,77.4 mg (0.5 mmol) of 4-chlorobenzamide,152 mg (1.0 mmol) of cesium fluoride,140 mg (0.55 mmol) of 4,4,5,5,4 ', 4', 5 ', 5'-octamethyl-2,2'-bi (1,3,2-dioxaborolanyl)180 mg (1.05 mmol) of trimethyl (2,2,2-trifluoroethoxy) silane and 0.5 mL of 1,4-dioxane were added and sealed,And the mixture was stirred at 100 ° C. for 12 hours.After the reaction vessel was cooled to room temperature, 1 mL of a saturated aqueous solution of ammonium chloride was added, and the mixture was extracted three times with 8 mL of ethyl acetate, and the obtained organic phases were combined.The solvent was distilled off under reduced pressure, and the residue was purified using silica gel column chromatography (hexane: chloroform: ethyl acetate = 4: 1: 0 to 4: 1: 1)92 mg (white solid, yield 75percent) of 4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) benzamide was obtained. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In 1,4-dioxane at 95℃; | A mixture of 2-70 (1.0 g, 5 mmol), (PinB)2 (2.28 g, 9 mmol), Pd(dppf)C12DCM (408 mg, 0.5 mmol), KOAc (980 mg, 10 mmol) and dioxane (5 mL) was degassed with N2 and stirred at 95 °C overnight. The resulting mixture was filtered and the filtrate was concentrated and purified via column chromatography on silica gel eluting with DCM/MeOH from 20/1 to 10/1 to give intermediate 2-71 (yellow solid, 975 mg, 79percent yield). LCMS (m/z):248 [M+Hj . |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With tris-(dibenzylideneacetone)dipalladium(0); sodium acetate; tricyclohexylphosphine In 1,4-dioxane at 115 - 120℃; for 24 h; | 20.0 g of compound vii (0.102 mol), 38.7 g of bis(pinacolato)diboron (0.152 mol), 2.85 g of tricyclohexyl phosphine (0.010 mol), 4.65 g of tris(dibenzylideneacetone)dipalladium (0.005 mol) and 25.0 sodium acetate were added to 200ml 1,4-dioxane, heated to 115 ~ 120 , incubation reaction 24h, cooling to room temperature, adding purified water 200ml. Extracted twice with 200 ml of ethyl acetate, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give a reddish brown solid. The solid was added to 30 ml of t-butyl methyl ether, stirred for 2 h. A yellowish solid, i.e. 9-azoindole-5-boronic acid (compound vi), was filtered off and weighed 11.8 g in a yield of 72.0percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
30.5% | With potassium acetate In dimethyl sulfoxide at 80℃; for 4 h; | A mixture of tert-butyl 4-(4-bromo-3-methyl-pyrazol-l-yl)piperidine-l-carboxylate (2.7 g), 4,4,4',4>,5,5,5>,5>-octamethyl-2,2'-bi(l,3,2-dioxaborolane) (4.98 g), 1,1 '- bis(diphenylphosphino)ferrocenedichloropalladium(II) - CH2Cl2 adduct (0.634 g) and potassium acetate (2.31 g) in DMSO (40 ml) was stirred at 80 0C for 4 hours. The reaction mixture was allowed to cool to room temperature under stirring over a period of 1 hour, quenched with water (25 ml) and extracted with ethyl acetate (3 x 40 ml). The combined organic phases were washed with water (3 x 30 ml), brine (1 x 20 ml), dried over magnesium sulfate and concentrated. The residue was purified by flash chromatography on silica gel eluting with 10 to 30percent ethyl acetate in petroleum ether to afford tert-butyl 4-(3-methyl-4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-lH-pyrazol- l-yl)piperidine-l-carboxylate (0.937 g, 30.5 percent) as a white solid. NMR Spectrum(DMSOd): 1.24 (s, 12H), 1.41 (s, 9H), 1.71 (dd, IH), 1.76 (dd, IH), 1.89-1.96 (m, 2H), 2.22 (s, 3H), 2.85 (bs, 2H), 3.95-4.07 (m, 2H), 4.20-4.29 (m, IH), 7.82 (s, IH) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
868 mg | With potassium acetate; palladium diacetate; XPhos In acetonitrile at 75℃; for 18 h; Inert atmosphere | General procedure: Step 2: tert-butyl (2-(4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)phenyl)propan-2- yl)carbamate: The product from Step 1 above (6 g, 18.52 mmol, 97percent purity), bis- (pinacolato)diboron (5.82 g, 22.91 mmol), palladium(II) acetate (0.107 g, 0.477 mmol), potassium acetate (5.62 g, 57.3 mmol) and XPhos (0.457 g, 0.955 mmol) were combined in MeCN (50 ml). The vessel was purged with N2 then heated at 75 °C for 18 h. The reaction mixture was cooled, filtered through Celite®, washing with MeCN (2 x 50 ml), and concentrated in vacuo to afford a brown oil. The residue was partitioned between DCM (50 ml) and water (50 ml). The phases were separated and the organic phase was concentrated in vacuo to afford a brown soild. The crude product was purified by columnchromatography (220 g cartridge, 0-20percent EtOAc/isohexane) to afford the title compound (5.67 g, 15.1 mmol, 96percent purity) as an off-white solid. LCMS (Method 1): m/z 306 (M+H- C4H8)+ at 2.83 min. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In 1,4-dioxane at 110℃; for 2 h; Sealed tube; Microwave irradiation | Intermediate 114: 4-(4,4,5,5-Tetramethyl-1 ,2-dioxaborolan-2-yl)indolin-2-one (0793) A mixture of 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(l,3,2-dioxaborolane) (1.903 g, 7.49 mmol, commercially available from, for example, Fluorochem), 4-bromoindolin-2-one (1.038 g, 4.90 mmol, commercially available from, for example, Fluorochem), [1,1'- 7 s(diphenylphosphino)ferrocene]dichloropalladium(II), complex with dichloromethane [Pd(dppf)Cl2.DCM] (0.601 g, 0.73 mmol) and potassium acetate (1.480 g, 15.08 mmol) in 1,4-dioxane (30 mL) was stirred at 110 °C for 2 h. The mixture was allowed to cool to rt before being filtered through a 10 g celite cartridge. The cartridge was washed through with ethyl acetate (3 x 30 mL) and the combined filtrates were evaporated in vacuoto give a brown liquid which was re-dissolved in DCM (ca. 10 mL), loaded onto a 100 g SNAP silica cartridge and purified by Biotage SP4 semi-automated flash column chromatography eluting with a gradient of 20 to 50percent ethyl acetate in cyclohexane. The required fractions were combined and evaporated in vacuo, this was re-dissolved in DCM (ca. 10 mL), transferred to a tarred vial and the solvent evaporated under a stream of nitrogen. The residue was triturated with ether (5 x 5 mL), decanting away the mother liquor each time, and the residue dried under a stream of nitrogen and in vacuo to give the desired product 4-(4,4,5,5-tetramethyl-l,3,2- dioxaborolan-2-yl)indolin-2-one (941.8 mg, 3.63 mmol, 74 percent yield) as a cream solid. (0794) LCMS (2 min Formic): Rt = 0.93 min, [MH]+ = 260.3. |
74.2% | With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In 1,4-dioxane at 110℃; for 2 h; | A mixture of 4,4,4T,4T,5,5,5T,5T-octamethyl-2,2T-bi( 1,3, 2-d ioxaborolane) (1.9025 g, 7.49 mmol), 4-bromoindolin-2-one (1.0383 g, 4.90 mmol), [1,1’-Bis(d iphenylphosphino)ferrocene]dichloropallad ium(II), complex with dichloromethane (0.6005 g,0.734 mmol) and potassium acetate (1.4802 g, 15.08 mmol) in 1,4-Dioxane (30 mL) was stirred at110 °C for 2 hr. The mixture was allowed to cool to room temperature before being filtered througha lOg celite cartridge. The cartridge was washed through with ethyl acetate (3 x 30 mL) and thecombined filtrates were evaporated in vacuo to give to give a brown liquid, which was redissolved indichloromethane (ca. 10 mL), loaded onto a bOg SNAP silica cartridge and purified by Biotage 5P4semi-automated flash column chromatography eluting with a gradient of 20 to 50percent ethyl acetate incyclohexane. The required fractions were combined and evaporated in vacuo, the residue (which was on the verge of crystallisation) was re-dissolved in dichloromethane (ca. 10 mL), transferred to a tared vial, the solvent evaporated under a stream of nitrogen. The residue was triturated with ether (5 x 5 mL), decanting away the mother liquor each time, and the residue dried under a stream of nitrogen and in vacuoto give the desired product as a cream solid (941.8 mg, 3.63 mmol, 74.2 percent yield)LCMS (2 mm Formic): Rt = 0.93 mi [MH]+ = 260 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | With copper(l) iodide; lithium methanolate; bis[2-(diphenylphosphino)phenyl] ether In dimethyl sulfoxide at 50℃; for 16 h; | General procedure: Phenylpropiolic acid (439 mg, 3.0 mmol), B2pin2 (763 mg, 3.0 mmol), lithium methoxide (23 mg, 0.6 mmol), copper iodide (57 mg, 0.3 mmol), and Dpe-Phos (324 mg, 0.6 mmol) were added to a vial containing DMSO (5 mL). The suspension was stirred for 16 h at 50 °C. The reaction was monitored by TLC, and after the completion of the reaction, the reaction mass was cooled to 25–28 °C and quenched into a mixture of 50 mL of water and 50 mL of ethyl acetate. The ethyl acetate layer was washed with water (2 × 25 mL), brine (2 × 25 mL), and then dried over Na2SO4. Evaporation of the solvent under reduced pressure provided the crude product, which was purified by column chromatography (hexane:EtOAc = 9.5:0.5). |
57% | With copper(II) trifluoroacetate; sodium carbonate In 1,4-dioxane at 80℃; for 18 h; Inert atmosphere | General procedure: A Schlenk tube with a magnetic stirring bar was charged with 3-phenylpropiolic acid (1a, 68 mg, 0.5 mmol), bis(pinacolato)diboron (2a, 152 mg, 0.6 mmol), Cu(TFA)2 (29 mg, 10 molpercent), Na2CO3 (127 mg, 1.2 mmol), and 1,4-dioxane (2 mL) under N2. The reaction mixture was stirred at 80 °C for 18 h (monitored by TLC and GC). Upon completion of the reaction, the reaction mixture was then cooled to ambient temperature, diluted with ethyl acetate (20 mL), filtered through a plug of silica gel, and washed with ethyl acetate (20 mL). The organic layer was washed with saturated brine (20 mL×2) and dried over anhydrous Na2SO4. The solvents were removed via rotary evaporator and the residue was purified by flash chromatography (silica gel, ethyl acetate: petroleum ether=1:30) to give 89.7 mg of desired product 3a in 78 percent yield as a colorless oil. 1H NMR (400 MHz, CDCl3): δ 7.48–7.50 (m, 2H), 7.41 (d, 1H, J=18.5Hz), 7.29–7.32 (m, 3H), 6.18 (d, 1H, J=18.4Hz), 1.32 (s, 12H). 13C NMR (100 MHz, CDCl3): δ 148.5, 136.4, 127.9, 127.5, 126.0, 82.3, 23.8 |