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CAS No. : | 1026962-68-4 | MDL No. : | MFCD21365092 |
Formula : | C8H3BrF4O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | IFMFJFGMOSTGLZ-UHFFFAOYSA-N |
M.W : | 287.01 | Pubchem ID : | 10171656 |
Synonyms : |
|
Num. heavy atoms : | 15 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.12 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 6.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 46.06 |
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) : | -5.84 cm/s |
Log Po/w (iLOGP) : | 1.56 |
Log Po/w (XLOGP3) : | 3.12 |
Log Po/w (WLOGP) : | 4.88 |
Log Po/w (MLOGP) : | 3.79 |
Log Po/w (SILICOS-IT) : | 3.4 |
Consensus Log Po/w : | 3.35 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.56 |
Log S (ESOL) : | -3.75 |
Solubility : | 0.0512 mg/ml ; 0.000178 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.57 |
Solubility : | 0.0769 mg/ml ; 0.000268 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.78 |
Solubility : | 0.0472 mg/ml ; 0.000164 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 0.0 |
Synthetic accessibility : | 1.78 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-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 |
---|---|---|
67% | With copper(l) iodide; caesium carbonate In toluene at 100℃; for 0.333333h; | 18.1 Step 1: 2-fluoro-6-[3-fluoro-4-(trifluoromethoxy)phenoxy]-3-(trifluoromethyl)benzoic acid A pressure bottle was charged with 6-bromo-2-fluoro-3-(trifluoromethyl)benzoic acid (5 g, 17.42 mmol), cesium carbonate (11.35 g, 34.84 mmol) and 3-fluoro-4-(trifluoromethoxy)phenol (3.416 g, 17.42 mmol) in toluene (125 mL). The mixture was degassed with nitrogen. After ca. 2 minutes, copper (I) iodide (664 mg, 3.48 mmol) was added and the reaction was stirred at 100 °C for 20 minutes. The reaction was diluted with ethyl acetate and water. The phases were separated and the organic phase was washed with brine and dried over sodium sulfate. Trituration with hexane and filtration gave 2-fluoro-6- [3-fluoro-4-(trifluoromethoxy)phenoxy]-3-(trifluoromethyl)benzoic acid (4.7 g, 67%), which was used without further purification. ESI-MS m/z calc. 402.01, found 403.2 (M+l)+; retention time (Method B): 1.86 minutes (3 minute run). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With copper (I) iodide; Cs2CO3 In toluene at 100℃; for 1h; | 2.3 Step 3: 2-fluoro-6-[2-methoxy-4-(trifluoromethoxy)phenoxy]-3-(trifluoromethyl)benzoic acid A pressure flask was charged with 6-bromo-2-fluoro-3-(trifluoromethyl)benzoic acid (5 g, 17.42 mmol), 2-methoxy-4-(trifluoromethoxy)phenol (4.35 g, 20.90 mmol), cesium carbonate (11.35 g, 34.84 mmol) and toluene (50 mL). The mixture was degassed with nitrogen. After ca. 2 minutes, copper (I) iodide (663 mg, 3.48 mmol) was added and the reaction was stirred at 100 °C for lhr. The reaction was diluted with 300mL ethyl acetate and 200mL of water and the phases were separated. The aqueous layer was acidified to pH~3 and extracted with ethyl acetate. The combined organic phases were dried over sodium sulfate, filtered and concentrated. The residue was purified by silica gel chromatography (ethyl acetate/hexane gradient, followed by 9: 1 dichloromethane: methanol) to afford 2-fluoro-6-[2- methoxy-4-(trifluoromethoxy)phenoxy]-3-(trifluoromethyl)benzoic acid (5.4503 g, 76%) as a pale green solid. ESI-MS m/z calc. 414.03, found 415.0 (M+l)+; retention time (Method B): 1.94 minutes (3 minute run). NMR (400 MHz, DMSO-d6) δ 7.53 (t, J = 8.4 Hz, 1H), 7.27 - 7.11 (m, 2H), 6.99 (ddd, J = 8.8, 2.7, 1.3 Hz, 1H), 6.49 (d, J = 8.8 Hz, 1H), 3.80 (s, 3H) ppm. |
76% | With copper (I) iodide; Cs2CO3 In toluene at 100℃; for 1h; | 3.3 Step 3: 2-fluoro-6-[2-methoxy-4-(trifluoromethoxy)phenoxy]-3-(trifluoromethyl)benzoic acid A pressure flask was charged with 6-bromo-2-fluoro-3-(trifluoromethyl)benzoic acid (5.00 g, 17.4 mmol), 2-methoxy-4-(trifluoromethoxy)phenol (4.35 g, 20.9 mmol), CS2CO3 (11.35 g, 34.84 mmol) and toluene (50 mL). The mixture was degassed with nitrogen. After ~2 minutes, copper (I) iodide (663 mg, 3.48 mmol) was added and the reaction was stirred at 100 °C for 1 hour. The reaction was diluted with 300 mL ethyl acetate and 200 mL of water and the phases were separated. The aqueous layer was acidified to pH~3 and extracted with ethyl acetate. The combined organic phases were dried over Na2SC>4, filtered and concentrated. The residue was purified by silica gel chromatography (ethyl acetate/hexanes gradient, followed by 10% methanol/dichloromethane) to afford 2-fluoro-6-[2-methoxy- 4-(trifhioromethoxy)phenoxy]-3-(trifhioromethyl)benzoic acid (5.45 g, 76%). ESI-MS m/z calc. 414.03, found 415.0 (M+l)+; retention time (Method B): 1.94 minutes. 1 H N R (400 MHz, DMSO-d6) d 7.53 (t, J = 8.4 Hz, 1H), 7.27 - 7.11 (m, 2H), 6.99 (ddd, J = 8.8, 2.7, 1.3 Hz, 1H), 6.49 (d, J = 8.8 Hz, 1H), 3.80 (s, 3H) ppm. |
76% | With copper (I) iodide; Cs2CO3 In toluene at 100℃; for 1h; Inert atmosphere; | 5.2; 206.3 Step 2: 2-fluoro-6-[2-methoxy-4-(trifluoromethoxy)phenoxy]-3-(trifluoromethyl)benzoic acid A pressure flask was charged with 6-bromo-2-fluoro-3-(trifluoromethyl)benzoic acid (5 g, 17.42 mmol), 2-methoxy-4-(trifluoromethoxy)phenol (4.35 g, 20.90 mmol), cesium carbonate (11.35 g, 34.84 mmol) and toluene (50 mL). The mixture was degassed with nitrogen. After ca.2 minutes, copper (I) iodide (663 mg, 3.48 mmol) was added and the reaction was stirred at 100 °C for 1hr. The reaction was diluted with 300mL ethyl acetate and 200mL of water and the phases were separated. The aqueous layer was acidified to pH~3 and extracted with ethyl acetate. The combined organic phases were dried over sodium sulfate, filtered and concentrated. The residue was purified by silica gel chromatography (ethyl acetate/hexane gradient, followed by 9:1 dichloromethane:methanol) to afford 2-fluoro-6-[2- methoxy-4-(trifluoromethoxy)phenoxy]-3-(trifluoromethyl)benzoic acid (5.4503 g, 76%) as a pale green solid. ESI-MS m/z calc.414.03, found 415.0 (M+1)+; retention time (Method B): 1.94 minutes. 1H NMR (400 MHz, DMSO-d6) d 7.53 (t, J = 8.4 Hz, 1H), 7.27 - 7.11 (m, 2H), 6.99 (ddd, J = 8.8, 2.7, 1.3 Hz, 1H), 6.49 (d, J = 8.8 Hz, 1H), 3.80 (s, 3H) ppm. |
45% | With Cs2CO3 In toluene at 100℃; for 1.5h; Inert atmosphere; | A41.1 Step 1, synthesis of intermediate 8 Compound 6 (450 mg, 1.6 mmol) was added to toluene (10 mL), Cs2CO3 (1.25 g, 3.84 mmol) and compound 7 (391 mg, 1.9 mmol) were added, the mixture was stirred at 100°C under nitrogen protection for 1.5 h, LC-MS showed that the reaction of the raw materials was complete, the mixture was cooled to room temperature, filtered, and the filter cake was washed with EA (30 mL 3 ), the combined organic phase was evaporated to dryness and purified by normal phase column (PE/EA=0-100%) to obtain compound 8, white solid, 300 mg, yield 45%, LCMS: m/z 415.2(M+H)+. |
45% | With Cs2CO3 In toluene at 100℃; for 1.5h; Inert atmosphere; | A41.1 Step 1, synthesis of intermediate 8 Compound 6 (450 mg, 1.6 mmol) was added to toluene (10 mL), Cs2CO3 (1.25 g, 3.84 mmol) and compound 7 (391 mg, 1.9 mmol) were added, the mixture was stirred at 100°C under nitrogen protection for 1.5 h, LC-MS showed that the reaction of the raw materials was complete, the mixture was cooled to room temperature, filtered, and the filter cake was washed with EA (30 mL 3 ), the combined organic phase was evaporated to dryness and purified by normal phase column (PE/EA=0-100%) to obtain compound 8, white solid, 300 mg, yield 45%, LCMS: m/z 415.2(M+H)+. |
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