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CAS No. : | 1233026-11-3 | MDL No. : | MFCD11520114 |
Formula : | C7H4BrF4N | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | FNWBXSBUORVUQH-UHFFFAOYSA-N |
M.W : | 258.01 | Pubchem ID : | 52982884 |
Synonyms : |
|
Num. heavy atoms : | 13 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.14 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 43.51 |
TPSA : | 26.02 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) : | -5.8 cm/s |
Log Po/w (iLOGP) : | 1.82 |
Log Po/w (XLOGP3) : | 2.92 |
Log Po/w (WLOGP) : | 4.77 |
Log Po/w (MLOGP) : | 3.71 |
Log Po/w (SILICOS-IT) : | 3.26 |
Consensus Log Po/w : | 3.3 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.55 |
Solubility : | 0.0719 mg/ml ; 0.000279 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.13 |
Solubility : | 0.192 mg/ml ; 0.000745 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -4.06 |
Solubility : | 0.0225 mg/ml ; 0.0000871 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 0.0 |
Synthetic accessibility : | 1.82 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P264-P270-P301+P312-P330 | UN#: | N/A |
Hazard Statements: | H302-H315-H320-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 |
---|---|---|
51.33% | With bis-triphenylphosphine-palladium(II) chloride; triethylamine In 1,4-dioxane at 90℃; for 3h; Inert atmosphere; | 19.1 Step 1 To a solution of 3-bromo-4-fluoro-5-(trifluoromethyl)aniline (1 g, 3.88 mmol) and tributyl(1-ethoxyvinyl)stannane (1.96 mL, 5.81 mmol) in dioxane (10 mL) was added TEA (1.35 mL, 9.69 mmol) and Pd(PPh3)2Cl2 (272.04 mg, 387.58 μmol). The mixture was stirred under nitrogen at 90° C. for 3 h. The reaction was adjusted to pH=2 using 1M HCl and stirred for 16 h. The mixture was filtered, and the filtrate was extracted with EtOAc. The organic layer was poured into aq. KF and stirred for 20 min. The mixture was filtered, washed with brine, dried with anhydrous Na2SO4, and the solvent was removed under reduced pressure. The residue was purified by column chromatography to give 1-[5-amino-2-fluoro-3-(trifluoromethyl)phenyl]ethanone (440 mg, 51.33% yield). 1H NMR (400 MHz, methanol-d4) δ ppm 7.25 (d, J=4 Hz, 1H) 7.11 (d, J=4 Hz, 1H) 2.58 (d, J=4.63 Hz, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: triethylamine; bis-triphenylphosphine-palladium(II) chloride / 1,4-dioxane / 3 h / 90 °C / Inert atmosphere 2.1: titanium(IV) isopropylate / tetrahydrofuran / 3 h / 90 °C 2.2: 0.5 h / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: triethylamine; bis-triphenylphosphine-palladium(II) chloride / 1,4-dioxane / 3 h / 90 °C / Inert atmosphere 2.1: titanium(IV) isopropylate / tetrahydrofuran / 3 h / 90 °C 2.2: 0.5 h / 0 °C 3.1: hydrogenchloride / methanol / 3 h / 25 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: triethylamine; bis-triphenylphosphine-palladium(II) chloride / 1,4-dioxane / 3 h / 90 °C / Inert atmosphere 2.1: titanium(IV) isopropylate / tetrahydrofuran / 3 h / 90 °C 2.2: 0.5 h / 0 °C 3.1: hydrogenchloride / methanol / 3 h / 25 °C 4.1: (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; 1,8-diazabicyclo[5.4.0]undec-7-ene / N,N-dimethyl-formamide / 16 h / 25 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With bis-triphenylphosphine-palladium(II) chloride In 1,4-dioxane at 80℃; for 10h; Inert atmosphere; | 21-11.A [0728] Step A: To a solution of 3-bromo-4-fluoro-5-(trifluoromethyl)aniline (4.00 g, 15.5 mmol, 1.00 eq ), tributyl(1-ethoxyvinyl)tin(5.60 g, 15.5 mmol, 5.23 mL, 1.00 eq.), and PdCl2(PPh)3 (326 mg, 0.47 mmol, 0.03 eq.) in 1,4-dioxane (10.0 mL) was stirred at 80 °C for 10 hours under a nitrogen atmosphere. The r mixture was cooled to 25 °C, poured into saturated potassium fluoride aqueous solution (200 mL) and stirred for 30 minutes to give a suspension, and the suspension was filtered, then the filtrate was solution was extracted with ethyl acetate (200 mL x 3). The combined organic layers were washed with brine (200 mL), dried over sodium sulfate, filtered, and concentrated under reduced pressure to give a crude product 3-(1-ethoxyvinyl)-4-fluoro-5-(trifluoromethyl)aniline (6.00 g, 24.1 mmol, 1.00 eq., crude) which was used into the next step without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With bis-triphenylphosphine-palladium(II) chloride In toluene at 120℃; for 12h; Inert atmosphere; | 35.1 first step Under nitrogen protection, compound 35-1 (6.00 g, 23.3 mmol) was dissolved in dry toluene (100 mL), compound 3-2 (12.6 g, 34.9 mmol) was added, and bistriphenylphosphine palladium dichloride ( 1.63 g, 2.33 mmol), the reaction solution was stirred at 120 ° C for 12 hours, and after cooling to room temperature, a saturated aqueous potassium fluoride solution (100 mL) was added to the reaction solution, extracted with ethyl acetate (100 mL×2), and the organic phase was Dry over anhydrous sodium sulfate, filter, and concentrate under reduced pressure to obtain crude compound 35-2, which is directly used in the next step. | |
With bis-triphenylphosphine-palladium(II) chloride In toluene at 120℃; Inert atmosphere; | 27.1 first step Under nitrogen protection, compound 27-1 (6.00 g, 23.3 mmol) was dissolved in dry toluene (100 mL), compound 14-6 (12.6 g, 34.9 mmol) was added, and bistriphenylphosphine palladium dichloride ( 1.63 g, 2.33 mmol), the reaction solution was stirred at 120 ° C for 12 hours, and after cooling to room temperature, a saturated aqueous potassium fluoride solution (100 mL) was added to the reaction solution, extracted with ethyl acetate (100 mL×2), and the organic phase was Dry over anhydrous sodium sulfate, filter, and concentrate under reduced pressure to obtain crude compound 27-2, which is directly used in the next step. |
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