Structure of 2-Bromo-3-methylpyridine
CAS No.: 3430-17-9
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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.
Synonyms: 2-Bromo-3-picoline
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Batch number can be found on the product's label following the word 'Batch'.
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CAS No. : | 3430-17-9 |
Formula : | C6H6BrN |
M.W : | 172.02 |
SMILES Code : | CC1=CC=CN=C1Br |
Synonyms : |
2-Bromo-3-picoline
|
MDL No. : | MFCD00239380 |
InChI Key : | PZSISEFPCYMBDL-UHFFFAOYSA-N |
Pubchem ID : | 220832 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 8 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.17 |
Num. rotatable bonds | 0 |
Num. H-bond acceptors | 1.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 36.9 |
TPSA ? Topological Polar Surface Area: Calculated from |
12.89 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.85 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
2.24 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.15 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
1.58 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
2.54 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.07 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.87 |
Solubility | 0.231 mg/ml ; 0.00134 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.15 |
Solubility | 1.23 mg/ml ; 0.00714 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-3.26 |
Solubility | 0.0948 mg/ml ; 0.000551 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 |
-5.76 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 |
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 |
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) |
1.56 |
* 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 |
---|---|---|
93.6% | With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); triethylamine; at 80℃; under 2585.81 Torr; for 16h; | A mixture of 2-bromo-3-methylpyridine (5.0 g, 29.0 mmol), Pd(dppf)C12 (2.1 g, 2.9 mmol), and triethylamine (8.8 g, 87 mmol) in methanol (250 mL) was stirred at 80 C under CO atmosphere (50 psi) for 16 h. The mixture was filtered and the filtrate concentrated in vacuo, then purified by column chromatography on Si02 to give the desired product (4.1 g, 93.6%). LCMS (mlz): 152.0 (M+1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
52% | With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate; In 1,2-dimethoxyethane; water; at 80℃; | Example 83A tert-butyl 4-(3-methylpyridin-2-yl)benzoate A mixture of 2-bromo-3-methylpyridine (0.688 g, 4 mmol), <strong>[850568-54-6](4-(tert-butoxycarbonyl)phenyl)boronic acid</strong> (0.888 g, 4 mmol), potassium carbonate (1.16 g, 8.40 mmol), and PdCl2dppf (0.146 g, 0.2 mmol) in dimethoxyethane (8.5 mL) and water (4.7 mL) was heated at 80° C. overnight. The mixture was diluted with 50 mL of ether and was then washed with a solution of methanesulfonic acid (0.25 mL) in water (12 mL) and with brine sequentially. The organic layer was dried over Na2SO4, filtered, and concentrated in vacuo. The crude material was purified by silica gel chromatography (0 to 50percent EtOAc-heptanes, eluent) to afford the title compound as a yellow oil (0.560 g, 52percent). 1H NMR (400 MHz, CDCl3) delta 8.55 (m, 1H), 8.07 (d, J=8.3 Hz, 2H), 7.65-7.52 (m, 3H), 7.21 (dd, J=7.8, 4.8 Hz, 1H), 2.34 (s, 3H), 1.58 (s, 9H). MS (DCI+) m/z 270.0 (M+H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | With bis(triphenylphosphine)nickel(II) chloride; potassium carbonate; In N,N-dimethyl-formamide; at 90℃; for 24h;Schlenk technique; Inert atmosphere; | Add bis(p-methoxy)phenylphosphorus oxide (0.952g, 5mmol), 2-bromo-3-methylpyridine (0.60mL, 6mmol), K2CO3 (1.38) to 100mL Schlenk reaction flask under nitrogen atmosphere. g, 10mmol). Ni(PPh3)Cl2 (159.25mg, 0.25mmol), DMF (5mL), and stirred at 90C for 24h. After the reaction, the mixture was diluted with water and extracted three times with ethyl acetate. The organic phase was washed with saturated sodium chloride solution, dried with anhydrous sodium sulfate, the mixture was chromatographed on silica gel column, eluted with petroleum ether/ethyl acetate=2:1, and drained to obtain a white solid (0.88g, 2.5mmol). The rate is 50%. |
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