Structure of 58530-53-3
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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.
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Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
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CAS No. : | 58530-53-3 |
Formula : | C5H3Br2N |
M.W : | 236.89 |
SMILES Code : | C1=C(N=CC=C1Br)Br |
MDL No. : | MFCD01859720 |
InChI Key : | PCMMSLVJMKQWMQ-UHFFFAOYSA-N |
Pubchem ID : | 817104 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 8 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.0 |
Num. rotatable bonds | 0 |
Num. H-bond acceptors | 1.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 39.64 |
TPSA ? Topological Polar Surface Area: Calculated from |
12.89 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.02 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
2.57 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.61 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
2.01 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
2.8 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.4 |
Log S (ESOL):? ESOL: Topological method implemented from |
-3.48 |
Solubility | 0.0779 mg/ml ; 0.000329 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.49 |
Solubility | 0.769 mg/ml ; 0.00325 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-3.74 |
Solubility | 0.0435 mg/ml ; 0.000184 mol/l |
Class? Solubility class: Log S scale |
Soluble |
GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg |
High |
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg |
Yes |
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) |
No |
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 |
-5.92 cm/s |
Lipinski? Lipinski (Pfizer) filter: implemented from |
0.0 |
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 |
1.0 |
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 |
1.0 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) |
1.92 |
* 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 |
---|---|---|
In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a suspension of 2,4-dibromo-pyridine (1.90 g, 8.02 mmol) in dry Et2O (40 mL) was treated with n-BuLi (3.36 mL of a 2.5M solution in hexanes, 8.42 mmol) at -78 0C. The reaction mixture was stirred at this temperature for 30 min. lambda/,lambda/-Dimethyl- formamide (0.78 mL, 10.03 mmol) was then added and the mixture allowed to warm to rt over a period of 1 h and stirred at this temperature for 20 min. The reaction was quenched by the addition of sat. aq. NH4CI (30 mL). The layers were separated and the aq. layer extracted with Et2O (3 x 50 mL). The combined org. extracts were dried over Na2SO4, filtered, and the solvent removed under reduced pressure. Purification of the residue by FC (10:1 to 2:1 hept-EA) gave the title compound as a white solid. TLC: rf (1 :1 hept-EA) = 0.44. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
6%; 89% | With palladium diacetate; triphenylphosphine; potassium hydroxide; In acetonitrile; for 24h;Inert atmosphere; Reflux; | General procedure: 2,4-dibromopyridine (0.12 g, 0.50 mmol), phenylboronic acid pinacol ester (0.11 g, 0.55 mmol), KOH (56 mg, 1.0 mmol), Pd(OAc)2 (11 mg, 5 mol %), PPh3 (52 mg, 20 mol %) were dissolved in CH3CN (6 mL). The reaction was stirred at 70 C under nitrogen atmosphere for 24 h and then cooled. The solid was filtrated off and the filtrate was concentrated. The crude product was then dissolved in CH2Cl2 (10 mL) and the solution was washed with water (10 mL*3) and brine (10 mL), and dried over sodium sulfate. Upon evaporation, the resulting residue was subjected to column chromatography (petroleum ether/AcOEt, 400:1) to give 3w (104 mg, 89%) as a colorless liquid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
13%; 9%; 37% | With palladium(II) trifluoroacetate; triphenylphosphine; potassium hydroxide; In acetonitrile; at 30℃; for 24h;Inert atmosphere; | General procedure: 2,5-dibromopyridine (0.12 g, 0.50 mmol), phenylboronic acid (67 mg, 0.55 mmol), K2CO3 (0.14 g, 1.0 mmol), Pd(OAc)2 (11 mg, 5 mol %), PPh3 (26 mg, 10 mol %) were dissolved in CH3CN/CH3OH (2:1, 6 mL). The solution was stirred at 50 C under nitrogen atmosphere for 24 h and then cooled and the solid was filtered off. The filtrate was then concentrated and the resulting crude product was dissolved in CH2Cl2 (10 mL). The solution was washed with water (10 mL*3) and brine (10 mL), and dried over sodium sulfate. Upon removal of the solvent with a rotavapor, the resulting residue was subjected to column chromatography (petroleum ether/AcOEt, 400:1) to give the desired product 3a (114 mg, 97%) as a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1.6 g | With 18-crown-6 ether; copper; potassium carbonate; In N,N-dimethyl-formamide; at 150℃; for 10h; | 2.40 g (12.05 mmol) of <strong>[6933-49-9]2-methoxycarbazole</strong>, 4.28 g (18.05 mmol) of 3,5-dibromopyridine, 1.53 g (24.10 mmol) of Cu powder, 6.65 g (48.20 mmol) of potassium carbonate, and 0.315 g (1.200 mmol) of 18-Crown-6 were suspended in 50 mL of dimethylformamide purified by fractional distillation, and then stirred at a temperature of 150 C. for 10 hours. An organic layer was extracted from the reaction mixture by using ethyl acetate and distilled water. The extracted organic layer was dried by using magnesium sulfate and then filtered. Then, the residue obtained therefrom was purified by column chromatography (1/3=dichloromethane/normal hexane) to obtain 1.6 g of Intermediate A. |