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CAS No. : | 328-67-6 | MDL No. : | MFCD03412186 |
Formula : | C8H4BrF3O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | AMZBKZQMAZWIJM-UHFFFAOYSA-N |
M.W : | 269.02 | Pubchem ID : | 11086788 |
Synonyms : |
|
Num. heavy atoms : | 14 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.12 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 5.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 46.1 |
TPSA : | 37.3 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) : | 1.7 |
Log Po/w (XLOGP3) : | 3.02 |
Log Po/w (WLOGP) : | 4.32 |
Log Po/w (MLOGP) : | 3.38 |
Log Po/w (SILICOS-IT) : | 2.95 |
Consensus Log Po/w : | 3.07 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.56 |
Log S (ESOL) : | -3.6 |
Solubility : | 0.0683 mg/ml ; 0.000254 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.47 |
Solubility : | 0.0915 mg/ml ; 0.00034 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.51 |
Solubility : | 0.0831 mg/ml ; 0.000309 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 0.0 |
Synthetic accessibility : | 1.69 |
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 |
---|---|---|
90% | With N-Bromosuccinimide; sulfuric acid In trifluoroacetic acid at 18 - 22℃; for 0.5 h; | a) Compound 1.2; 36 N H2SO4 (1.5 mL) and NBS (2.75 g, 15.0 mmol) were added to a solution of acid 1.1 (1.90 g, 10.0 mmol) in TFA (5 mL) at room temperature. After stirring for 30 min the reaction mixture was poured into water (200 mL) with vigorous stirring. The suspension was filtered and the resulting solid was rinsed with water and dried to give compound 1.2 (2.45 g, 90percent yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | Stage #1: With hydrogen bromide; sodium nitrite In water at 0℃; for 1 h; Stage #2: With copper(ll) bromide In water at 20℃; for 16 h; |
Step B: 3-Bromo-5-(trifluoromethyl)benzoic acid To a stirred suspension of 3-amino-5-(trifluoromethyl)benzoic acid (7.90 gm, 38.5 mmol) in a mixture of hydrobromic acid (43percent w/v, 100 mL) and water (100 mL) at 0° C. was slowly added a solution of sodium nitrite (7.97 gm, 0.116 mol) in water (50 mL). After 1 hour the inhomogeneous yellow liquid was added to a solution of copper (II) bromide (16.44 gm, 0.115 mol) in water (100 mL) and the mixture was stirred at room temperature for 16 hours. The mixture was extracted with diethyl ether (250 mL), the aqueous layer was separated and extracted with diethyl ether (3*75 mL). The combined organic layers were dried with anhydrous sodium sulfate and the solvent removed under vacuum to give the title compound as a yellow solid (9.0 gm, 87percent) which was used in the following reaction without further purification. LC-MS (ES-) Calc: 269, Found: 268 (M-H). 1H NMR (CD3OD) δ ppm 8.38 (brs, 1H), 8.23 (brs, 1H), 8.09 (brs, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69% | Stage #1: With borane-THF In tetrahydrofuran at 65℃; for 2 h; Stage #2: With water; sodium hydrogencarbonate In tetrahydrofuran |
16). Synthesis of 1-bromomethyl-3-methanesulfonyl-5-trifluoromethyl-benzene; To a solution of 3-bromo-5-(trifluoromethyl)benzoic acid (5 mmol, 1.35 g) in THF (8 mL) is added 1M boran in THF (16 mmol, 16 ml_) under nitrogen. The solution is allowed to warm to 65 0C and stirred for 2 hours. The mixture is cooled to room temperature, then poured into saturated aq. NaHCO3. The mixture is extracted with EtOAc. The combined organic layer is washed with brine, dried over Na2SO4, filtrated, and concentrated under reduced pressure. The residue is purified by silica gel column chromatography (eluent: hexane / EtOAc) to give (3-bromo-5-trifluoromethyl-phenyl)-methanol (418 mg, 69percent). |
57% | Stage #1: With dimethylsulfide borane complex In tetrahydrofuran at 20℃; for 20 h; Stage #2: With methanol In tetrahydrofuran |
Step C: (3-Bromo-5-(trifluoromethyl)phenyl)methanol To a solution of 3-bromo-5-(trifluoromethyl)benzoic acid (2.13 gm, 7.92 mmol) in anhydrous THF under nitrogen was added borane dimethylsulfide complex (15.83 mmol, 7.91 mL) and the mixture was stirred at room temperature for 16 hours. A further aliquot of borane dimethylsulfide complex (15.83 mmol, 7.91 mL) was then added and stirring was continued at room temperature for a further 4 hours. LC-MS indicated complete consumption of starting material. Methanol was added cautiously until effervescence ceased then 2N hydrochloric acid (20 mL) was added. The mixture was stirred at room temperature for 20 hours then concentrated to dryness under reduced pressure. The residue was extracted with diethyl ether and the solution washed with water. The organic layer was dried with anhydrous sodium sulfate and the solvent removed under vacuum. The residue was dissolved in a mixture of dichloromethane and methanol, silica gel was added and the solvent removed under vacuum. The solid was placed on a column of silica gel (50 gm) and eluted with hexane-ethyl acetate (85:15) to give the title compound as a yellow oil which crystallized on standing (1.16 gm, 57percent). LC-MS (ES-) Calc: 255, Found: 254 (M-H). 1H NMR (CDCl3) δ ppm 7.72 (brs, 1H), 7.69 (brs, 1H), 7.57 (brs, 1H), 4.77 (s, 2H), 1.86 (brs, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With trans-N,N'-dimethyl-1,2-cyclohexyldiamine; potassium phosphate; copper(l) iodide In 1,4-dioxane at 115℃; for 72 h; Molecular sieve | Coupling reaction: A reaction flask was charged with 3-bromo-5-trifluoromethylbenzoic acid (compound 2, 2.7 g, 0.01 mol), 4-methyl-1H- imidazole (1.64 g, 1), trans- N, N'-dimethylcyclohexanediamine (0.28 g, 0.002 mol), 1,4-dioxane (10 vol./g), anhydrous potassium phosphate , 0.03mol) and 4A molecular sieves (0. lg / g), to form a mixed system; the mixed system is purged with nitrogen to have an oxygen content of 500ppm, finally adding cuprous iodide (0.38g, 0.002mol) The system was heated to 115 ° C, the reaction was stirred for 72 hours, TLC showed compound 2 disappeared to give the product system; and then the system was cooled to room temperature, transferred to 2M hydrochloric acid quenched, concentrated filtered without fraction To be purified solution. Adding n-butanol, extracting and separating the organic phase, extracting with n-butanol twice, and combining the organic phases; concentrating the organic phase to remove n-butanol to obtain 3- (4-methyl- -5- (trifluoromethyl) benzoic acid (Compound 3) crude. Recrystallization from methanol (4: 1 ./g) gave 1.76 g of a khaki-colored solid in 65percent yield. |
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