Structure of 185112-61-2
*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.
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'.
CAS No. : | 185112-61-2 |
Formula : | C18H12BrN |
M.W : | 322.20 |
SMILES Code : | BrC1=CC=CC(=C1)N1C2=CC=CC=C2C2=CC=CC=C12 |
MDL No. : | MFCD20486475 |
InChI Key : | ZKGHGKNHPPZALY-UHFFFAOYSA-N |
Pubchem ID : | 58690888 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 20 |
Num. arom. heavy atoms | 19 |
Fraction Csp3 | 0.0 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 0.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 88.48 |
TPSA ? Topological Polar Surface Area: Calculated from |
4.93 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
3.28 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
6.54 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
5.55 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
5.01 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
4.74 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
5.02 |
Log S (ESOL):? ESOL: Topological method implemented from |
-6.59 |
Solubility | 0.0000819 mg/ml ; 0.000000254 mol/l |
Class? Solubility class: Log S scale |
Poorly soluble |
Log S (Ali)? Ali: Topological method implemented from |
-6.44 |
Solubility | 0.000117 mg/ml ; 0.000000362 mol/l |
Class? Solubility class: Log S scale |
Poorly soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-7.48 |
Solubility | 0.0000107 mg/ml ; 0.0000000331 mol/l |
Class? Solubility class: Log S scale |
Poorly soluble |
GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg |
Low |
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg |
No |
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) |
No |
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) |
Yes |
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) |
Yes |
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) |
No |
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) |
No |
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) |
No |
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from |
-3.62 cm/s |
Lipinski? Lipinski (Pfizer) filter: implemented from |
1.0 |
Ghose? Ghose filter: implemented from |
None |
Veber? Veber (GSK) filter: implemented from |
0.0 |
Egan? Egan (Pharmacia) filter: implemented from |
0.0 |
Muegge? Muegge (Bayer) filter: implemented from |
2.0 |
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat |
0.55 |
PAINS? Pan Assay Interference Structures: implemented from |
0.0 alert |
Brenk? Structural Alert: implemented from |
0.0 alert: heavy_metal |
Leadlikeness? Leadlikeness: implemented from |
No; 1 violation:MW<1.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
2.16 |
* 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 |
---|---|---|
83% | With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; for 6h; | P3 (65 g, 1 eq), Bis (pinacolato) diboron ( bis (pinacolato) diboron) (65 g 1.5 eq), PdCl2 (dppf) (11 g, 0.1 eq), KOAc (50 g, 3 eq), Dioxane 800ml Is placed in a round bottom flask (1-neck-R.B.F.) and stirred. (6h) A silica / celite filter was applied, Compound P2 was obtained. (60 g, Step yield = 83%) |
81% | With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In tetrahydrofuran; at 80℃; for 5h;Inert atmosphere; | In a 100 ml three-necked flask, first S15 (1.35 mmol), bis(pinacolato)diboron(1.65 mmol),(1,1'-bis (diphenylphosphine) ferrocene) dichloropalladium (II) (0.05mmol) and potassium acetate (9mmol) were added separately,While stirring, degassing and nitrogen replacement were repeated 3 times quickly, and 6 mL of tetrahydrofuran was added through a syringe.Stir at a certain speed, and heat the resulting mixed solution reactant under reflux at a reaction temperature of 80 C. for 5 h;After the reaction is completed, cool to room temperature and add 6 ml of water, extract with ether, and dry the obtained organic phase with anhydrous sodium sulfate.The solvent was distilled off and purified by column chromatography to obtain intermediate S10 (1.1 mmol, 81%). |
80% | With potassium acetate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In dimethyl sulfoxide; at 60 - 80℃; for 9.25h; | Under nitrogen flow, the target compound 11 (10.5 g), bis(pinacolate)diboron (9.93 g), potassium acetate (10.9 g), and anhydrous dimethylsulfoxide (190 ml) were stirred while heating to 60C for 15 min, and [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane complex (0.799 g) was added thereto. The resulting mixture was stirred while heating to 80C for 9 hr and then allowed to cool to room temperature. To the reaction solution, water (250 ml) and toluene (500 ml) were added, and the resulting mixture was stirred. After the water layer was reextracted twice with toluene, the organic layers were mixed. Further, magnesium sulfate and active clay were added thereto. The magnesium sulfate and active clay were removed by filtration, and the toluene was evaporated under reduced pressure. The precipitated crystal was washed with cold methanol and dried under reduced pressure to obtain a target compound 12 (9.86%, yield: 80%) as a white crystal. |
76% | With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; tris-(dibenzylideneacetone)dipalladium(0); potassium acetate; In 1,4-dioxane; for 24h;Inert atmosphere; Reflux; | In 500 mL three-necked flask, followed by adding intermediate M7 (20g, 62.lmmol), bis (pinacolato) diboron (23.6g, 93.2mmol), CH3COOK (17.5g, 178.2mmol), 1, 4- dioxane, 300 mL, and S-phos (5.35g, 13.04mmol), N2 replaced three times, was added Pd2 (dba) 3 (3.98g, 4.35mmol) and heated to reflux. After 24h the reaction was stopped.It cooled to room temperature, filtered, and the filtrate was collected, concentrated, and purified by column chromatography (dichloromethane: n-hexane = 0-1 as the mobile phase), to receive an off-white solid 17.4g (76%), |
70% | With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In tetrahydrofuran; 1,4-dioxane; at 85℃; for 24h; | In a 250 mL single-mouth reaction flask, Compound 5 (5.00 g, 15.52 mmol) was added separately.Potassium acetate (7.90 g, 80.70 mmol) and bis(pinacol) diboron (4.88 g, 18.62 mmol), Pd(dppf) 2Cl2 (0.23 g, 0.31 mmol),Then, 100 mL of anhydrous tetrahydrofuran was added, followed by heating to 85 C under nitrogen for 24 hours.After completion of the reaction, it was cooled to room temperature, then 100 mL of water was added, extracted with dichloromethane, and the organic phase was collected and washed with water several times.The organic phase was dried over anhydrous magnesium sulfate and the solvent was evaporated with stirring.The column chromatography eluent was ethyl acetate/petroleum ether = 10/1, yielding a white solid, 4.2 g, yield 70%. |
69% | With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In N,N-dimethyl-formamide; at 85℃;Inert atmosphere; | A mixture of 1B (6.55 g, 20.4 mmol), bis(pinacolato)diboron (6.22 g, 24.5 mmol), [1,1?-Bis(diphenylphosphino)ferrocene]dichloropalladium (747 mg, 1.02 mmol), and potassium acetate (5.88 g, 60 mmol) in dimethylformamide (DMF) (anhydrous, 50 mL) was degassed for 45 minutes. The mixture was further degassed by being heated to about 85 C. overnight under argon. After cooling to RT, the mixture was poured into DCM (250 mL) and solids were filtered off. The filtrate was washed with water (2×300 mL), dried over sodium sulfate, and loaded onto silica gel. Flash column (gradient of 10% to 30% DCM in hexanes) and precipitation from DCM/MeOH gave 5.17 g of 1C; 69% yield, pure by HNMR. |
68% | With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 80℃; for 24h;Inert atmosphere; | Step 1 in the manufacturing of the compound (3.0 g, 9.3 mmol), bis (pinacolato) di boron (2.6 g, 10 mmol), potassium acetate (2.7 g, 28 mmol) and [bis (diphenylphosphino)ferrocene] dichloropalladium (0) complex (0.32 g, 0.39 mmol) and then the presence of nitrogen, for 24 hours at 80 dissolved in dioxane (60 ml), and stirred. After the reaction was terminated, cooled to ambient temperature, the reaction mixture was filtered through celite. Pour water to the filtrate, extracted with ethyl acetate, and wash the organic layer extracted with brine. The washed organic layer was dried over magnesium sulfate and purified by column chromatography (silica gel), the desired compound (2.3 g, 68%) was obtained. |
68% | With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; at 100℃; for 26h;Inert atmosphere; | 4 was prepared as follows: a mixture of compound 3 (see Kido, J.; Su, S. -J.; Sasabe, H.; and, Takeda, T., Chem. Mater. 2008, 20(5), 1691-1693, which is incorporated by reference herein for its relevant teachings) (5.45 g, 16.9 mmol), bis(pinacolato)diboron (9.020 g, 35.52 mmol), [1,1'-bis(diphenylphosphino)-ferrocene]dichloropalladium(II) (0.743 g, 1.02 mmol), potassium acetate (4.980, 50.75 mmol) and anhydrous toluene (110 mL) was degassed with argon for 1 h. while stirring. The reaction mixture was then maintained under argon at 100 C. while stirring for 25 h. until TLC (SiO2, 4:1 hexanes-dichloromethane) confirmed consumption of the starting material. Upon completion, the reaction was cooled to RT and about 500 mL ethyl acetate added. The organics were then washed with saturated NaHCO3, H2O and brine, dried over MgSO4, filtered and concentrated in vacuo. The crude product was purified via flash chromatography (SiO2, 4:1 hexanes-dichloromethane to 100% dichloromethane) to afford Compound 4 (4.26 g, 68%) as a white solid. |
With potassium acetate;1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0); In 1,4-dioxane;Inert atmosphere; Reflux; | Step 2. 3-Bromophenyl carbazole (9.5 g, 29.5 mmol), bis(pinacolato)diboron (11.2 g, 44.2 mmol), potassium acetate (8.7 g), tris(dibenzylideneacetone)dipalladium (200 mg) and 1,1'-bis(diphenylphosphino)ferrocene (400 mg) are suspended in 200 mL of dioxane and heated to reflux under nitrogen atmosphere overnight. After cooling down and evaporation the residue is subjected to column chromatography on silica gel, providing 9-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-9H-carbazole b(6.0 g, colorless crystals). | |
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate; In N,N-dimethyl-formamide; for 6h;Reflux; | 9-(3-bromo-phenyl)-9H-carbazole (9-(3-bromophenyl)-9H-carbazole, 5g, 15.5mmol), bis(pinacolato)diboron (bis(pinacolato)diboron, 6.3g , 24.8mmol), KOAc 4.5g (46.5mmol), were dissolved Pd (dppf) Cl2CH2Cl2 1.13g (1.55mmol) in DMF100ml was refluxed for 6 hours. After cooling to room temperature after completion of the reaction was isolated by extraction with EA / H2O (Sat'd NaHCO3). The organic layer was dried over MgSO4 and evaporated under reduced pressure to remove the solvent. Separated by column chromatography to obtain the desired product compound 2-2. | |
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 85℃; for 4h;Inert atmosphere; | In a 500mL reaction flask, add intermediate M4 (11g, 34.45mmol), diboronic acid pinacol ester (13.12g, 51.68mmol), PdCl2 (dppf) (5.04g, 6.89mmol), CH3COOK (6.76g, 68.9mmol) Add 1,4-dioxane (10mL) and stir,Heated to 85 under nitrogen protection,After 4 hours of reaction, the reaction was monitored by TLC until the reaction was complete. The temperature was lowered to room temperature, filtered, and the reaction solution was concentrated.The product was separated and purified on a silica gel column, and concentrated to obtain a crude product, which was filtered with 100 mL of n-hexane to obtain intermediate M5. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | Under a nitrogen atmosphere, 129 g (0.4 mol) of the compound (E) was dissolved in 600 mL of THF and cooled to -60 C. 263 mL of normal butyllithium (1.6 M hexane solution) was added dropwise and the mixture was stirred for 1 hour. 81.87 g (0.44 mol) of 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane was added dropwise and the mixture was further stirred for 1 hour. The temperature of the mixture was raised to room temperature, neutralized with dilute hydrochloric acid, extracted with ethyl acetate / water, and the organic layer was washed with water and saturated brine and dried over magnesium sulfate. After distilling off the solvent under reduced pressure, purification with silica gel column chromatography (hexane / ethyl acetate) gave 105.5 g (yield 72%) of compound (F). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With Pd(pph3)Cl4; potassium carbonate; In ethanol; toluene; for 12.0h;Reflux; | 3-bromo-phenylcarbazole (20 g, 62 mmol), phenyl boronic acid (9.08 g, 74 mmol), Pd(pph3)C14 (0.7 g, 0.621 mmol) and K2C03 (17.2 g, 124 mmol) were dissolved in a mixture of ethyl alcohol (200 mE) and toluene (800 mE). The mixture was refluxed and stirred for 12 hours. The resultant was re-precipitated to obtain 9-(biphenyl-3-yl)-9H- carbazole (16.2 g, yield: 82%). |