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CAS No. : | 216393-64-5 | MDL No. : | MFCD01318110 |
Formula : | C6H5BBrFO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | PKZHIIVZRPUZSU-UHFFFAOYSA-N |
M.W : | 218.82 | Pubchem ID : | 2773333 |
Synonyms : |
|
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 43.93 |
TPSA : | 40.46 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.48 cm/s |
Log Po/w (iLOGP) : | 0.0 |
Log Po/w (XLOGP3) : | 1.62 |
Log Po/w (WLOGP) : | 0.69 |
Log Po/w (MLOGP) : | 1.48 |
Log Po/w (SILICOS-IT) : | 0.39 |
Consensus Log Po/w : | 0.84 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.55 |
Solubility : | 0.61 mg/ml ; 0.00279 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.08 |
Solubility : | 1.81 mg/ml ; 0.00828 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -2.43 |
Solubility : | 0.819 mg/ml ; 0.00374 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.99 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H319 | 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 |
---|---|---|
1.4% | Stage #1: (4-bromo-2-fluorophenyl)boronic acid With copper diacetate; n-tetradecanoic acid In toluene at 20℃; for 0.0833333h; Stage #2: With 2,6-dimethylpyridine In toluene at 20℃; for 0.166667h; Stage #3: 4-bromo-2-methyl-2H-pyrazol-3-ylamine In toluene at 20℃; | 1.58 Example 1.58; Preparation of the intermediate (4-bromo-2-fluoro-phenyl)-(4-bromo-2-methyl-2H-pyrazol- 3-yl)-amine.A 200-mL round bottom flask was charged with toluene (30 mL), copper(II) acetate (0.52 g, 2.86 mmol), myristic acid (0.98 g, 4.29 mmol), and 4-bromo-2-fluoro-phenyl boronic acid (5.00 g, 22.86 mmol) then stirred at room temperature for five minutes. While mixing, 2,6- lutidine (1.66 mL, 14.29 mmol) was added and allowed to stir for an additional 10 minutes. 3- amino-4-bromo-2-methyl pyrazole (2.52 g, 14.29 mmol) was added then reaction mixture stirred at room temperature overnight. Ethyl acetate was added, washed with ammonium hydroxide, water and brine. The ammonium salt formed, suspended in the organic layer, was removed by filtration. The filtrate was washed with water twice, dried over MgSO4 and filtered. The solvent was removed under reduced pressure to yield a crude material, that was purified by column chromatography on silica gel (Biotage, hexanes/dichlomethane, gradient elution) to afford (4- bromo-2-fluoro-phenyl)-(4-bromo-2-methyl-2H-pyrazol-3-yl)-amine. Yield: 0.07 g (1.4 %). LCMS: m/z (%) = 348 (M+Η79Br79Br, 40), 350 (M+H79Br 81Br, 100), 352 (MH-H81Br81Br, 46). 1H NMR (400MHz, MeOD): δ 7.43 (s, IH), 7.19 (d, J=10.0 Hz, IH), 7.01 (d, J=8.8 Hz, IH), 6.22 (t, J=8.8 Hz, IH), 3.62 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
54% | With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In 1,4-dioxane at 100℃; for 12h; | 33.1 Step 1: 4'-Bromo-2,2'-difluoro-[1,1'-biphenyl]-4-carboxylic acid methyl ester Add 4-bromo-2-fluorobenzeneboronic acid (0.50 g, 2.28 mmol) to a 100 mL single-mouth bottle.Methyl 3-fluoro-4-iodobenzoate (0.57 g, 2.06 mmol),Potassium carbonate (0.95 g, 6.87 mmol),[1,1'-bis(diphenylphosphino)ferrocene]palladium dichloride (84 mg, 0.11 mmol) and1,4-dioxane (20 mL). The reaction was stirred at 100 ° C for 12 h.Then concentrated under reduced pressure, and the residue obtained was applied to silica gel column chromatography(PE/EA(V/V)=100/1) purificationThe title compound was obtained as a colorless oil (0.40 g, 54%). |
54% | With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In 1,4-dioxane at 100℃; for 12h; | 33.1 Step 1: methyl 4’-bromo-2,2’-dffluoro- [1,1 ‘-diphenyll-4-carboxylate To a 100 mL single neck flask were added 4-bromo-2-fluorobenzene boronic acid (0.50 g, 2.28 mmol), methyl 3-fluoro-4-iodobenzene carboxylate (0.57 g, 2.06 mmol), potassium carbonate (0.95 g 6.87 mmol), [1,1’ -bis(diphenylphosphino)ferrocene]dichloropalladium (84 mg, 0.11 mmol) and 1,4-dioxane (20 mL). The reaction mixture was stirred at 100 °C for 12 hours and concentrated in vacuo. The residue was purified by silica gel column chromatography (PE/EtOAc (v/v) = 100/1) to give the title compound as colorless (0.40 g, 54%). ‘H NMR (400 1VIH4 DMSO-d6) 7.91 (dd, J= 8.0, 1.5 Hz; 1H), 7.84 (dd, J= 10.4, 1.3 Hz; 1H), 7.76 (dd, J9.8, 1.7 H4 1H), 7.66 (t, J= 7.7 H4 1H), 7.60 (dd, J= 8.3, 1.7 Hz; 1H), 7.50 (t, J= 8.1 H4 1H),3.91 (s, 3H). |
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