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CAS No. : | 35590-37-5 | MDL No. : | MFCD00174363 |
Formula : | C6H3BrN2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | FTFFHWWIPOQCBC-UHFFFAOYSA-N |
M.W : | 183.01 | Pubchem ID : | 736793 |
Synonyms : |
|
Num. heavy atoms : | 9 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 36.65 |
TPSA : | 36.68 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.52 cm/s |
Log Po/w (iLOGP) : | 1.47 |
Log Po/w (XLOGP3) : | 1.26 |
Log Po/w (WLOGP) : | 1.72 |
Log Po/w (MLOGP) : | 0.56 |
Log Po/w (SILICOS-IT) : | 2.02 |
Consensus Log Po/w : | 1.41 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.26 |
Solubility : | 1.0 mg/ml ; 0.00547 mol/l |
Class : | Soluble |
Log S (Ali) : | -1.63 |
Solubility : | 4.3 mg/ml ; 0.0235 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -2.96 |
Solubility : | 0.199 mg/ml ; 0.00109 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.64 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* 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 |
---|---|---|
68% | Stage #1: With isopropylmagnesium chloride; lithium chloride In tetrahydrofuran at -15℃; for 0.25 h; Stage #2: With N,N-dimethyl-formamide In tetrahydrofuran at 0℃; for 2 h; Stage #3: With ammonia; iodine In tetrahydrofuran; water at 20℃; for 2 h; |
General procedure: To a flask containing dried LiCl (0.35 g, 8.24 mmol) was added iPrMgCl (2 M in THF, 4.1 mL) and THF (5 mL) at 15° C. After beingstirred for 15 min, 3-bromo-1-benzonitrile (1.46 g, 8.03 mmol) inTHF (1 mL) was added to the reaction mixture and the obtainedmixture was stirred for 15 min. Then, DMF (1.3 mL, 12 mmol) wasadded at 0° C and the mixture was stirred for 2 h. Then, aq NH3 (7 mL, 28-30percent) and I2 (4.06 g, 16 mmol) were added to the reaction mixture. After being stirred for 2 h at room temperature, the reactionmixture was poured into satd aq Na2SO3 solution and was extracted with CHCl3 (3∗30 mL). The organic layer was dried over Na2SO4 and filtered. After removal of the solvent, the residue waspurified by short column chromatography on silica gel (eluent:hexane/ethyl acetate=9:1, v/v) to provide pure 1,3-dicyanobenzene (0.73 g) in 71percent yield. Most nitriles mentioned in this work are commercially availableand were identified by comparison with the authentic samples. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | at 315℃; for 1 h; | General procedure: Following the amide intermediate Preparation Example A. The reaction vessel is closed (when the amide intermediate has a boiling point at normal pressure equal to or lower than the reaction temperature TB described below) or the reaction vessel is kept open (when the amide intermediate has a boiling point higher than the normal pressure When the reaction temperature is TB), the stirring is continued (600 r/min), the reaction temperature is changed to TB, and after the reaction temperature TB is maintained for TD hours, the reaction is almost complete. Then, the reaction vessel was sealed and connected to a vacuum pump so that the degree of vacuum in the reaction vessel reached 20-50 mbar (according to the type of nitrile product) and the distillate was used as the nitrile product. The yield of the nitrile product was calculated and sampled for nuclear magnetic proteomics and elemental analysis to characterize the nitrile product obtained. Specific reaction conditions and characterization results are shown in Tables A-7, A-8, A-9, A-10 and A-11 below. These characterization results show that the nitrile product obtained has an extremely high purity (above 99percent).In these nitrile product preparation examples, 10 g of diphosphorus pentoxide was optionally added to the reaction vessel as a catalyst at the start of the reaction. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
56% | With pyridine; tetrakis(triphenylphosphine) palladium(0); ethanol In toluene for 20 h; Reflux | (0.01 mmol, 11.5 mg) was dissolved in toluene / ethanol (V: & lt; RTI ID = 0.0 & gt; V). & Lt; / RTI & gt; A solution of 3-bromo-5- cyanopyridine (1 mmol, 0.183 g) V = 3: 1). After the reaction was allowed to proceed for 20 hours under refluxing, the reaction was stopped. The reaction mixture was allowed to stand at room temperature and washed with dichloromethane. The organic phase was collected and purified by silica gel column chromatography to give a white solid 0.11 g (yield: 56percent) of 3-phenyl-5-amidopyridine; Ms (M / Z): 198.2 (M +). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
32% | With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 90℃; for 21 h; | A 500 ml 2-neck flask was charged with 3-bromo-5-cyanopyridine (0.63 g, 2.5 mmol), 1,1 bis (diphenylphosphino) ferrocene palladiumdichloride (0.17 g, 0.21 mmol), potassiumacetate (0.61 g, 6.21 mmol) Was dissolved in 6 mL of 1,4-dioxane, and the mixture was heated and stirred at 90 DEG C for 21 hours. After the completion of the reaction, the reaction mixture was cooled to room temperature and filtered through celite. The filtrate was distilled under reduced pressure and dried to obtain 0.1 g of compound F (yield: 32percent). |
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