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CAS No. : | 215453-84-2 | MDL No. : | MFCD11855868 |
Formula : | C11H13BrO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | KFYXVTLWTKYPLL-UHFFFAOYSA-N |
M.W : | 257.12 g/mol | Pubchem ID : | 16216127 |
Synonyms : |
|
Num. heavy atoms : | 14 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.45 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 58.83 |
TPSA : | 18.46 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | Yes |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.75 cm/s |
Log Po/w (iLOGP) : | 2.78 |
Log Po/w (XLOGP3) : | 2.99 |
Log Po/w (WLOGP) : | 3.01 |
Log Po/w (MLOGP) : | 2.42 |
Log Po/w (SILICOS-IT) : | 3.22 |
Consensus Log Po/w : | 2.88 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.5 |
Solubility : | 0.0807 mg/ml ; 0.000314 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.04 |
Solubility : | 0.234 mg/ml ; 0.000909 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.89 |
Solubility : | 0.033 mg/ml ; 0.000129 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 0.0 |
Synthetic accessibility : | 1.81 |
Signal Word: | Warning | Class: | |
Precautionary Statements: | P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313 | UN#: | |
Hazard Statements: | H315-H319 | Packing Group: | |
GHS Pictogram: |
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* 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 |
---|---|---|
86% | With di-isopropyl azodicarboxylate; triethylamine; triphenylphosphine In tetrahydrofuran at 0 - 20℃; | |
With triphenylphosphine; diethylazodicarboxylate In toluene at 0 - 20℃; for 0.75h; | 18.1 Step 1: Preparation of 4-(4-bromophenoxy)tetrahydro-2H-pyran (Compound of Formula 18-2) 4-bromophenol (Formula 18-1, 500 mg, 2.89 mmol), 4-hydroxytetrahydropyran (0.4 ml, 4.34 mmol, 1.5 eq) and triphenylphosphine (PPh3) (1.1 g, 4.34 mmol, 1.5 eq) was dissolved in toluene (8 ml), then diethyl azodicarboxylate (DEAD) (1.4 ml, 3.18 mmol, 1.1 eq) was added dropwise at 0 ° C. The reaction mixture was stirred at room temperature for 45 minutes. After completion of the reaction, the solvent was removed under reduced pressure, dissolved in diethyl ether, and the resulting solid was filtered off. Ethyl acetate was added to the filtrate, and the mixture was washed with H2O, dried over anhydrous MgSO4, and the solvent was removed under reduced pressure. Thereafter, the reaction mixture was separated and purified by MPLC to obtain the target compound (Formula 18-2). | |
With triphenylphosphine; diethylazodicarboxylate In toluene at 0 - 20℃; for 0.75h; | 18.1 Step 1: Preparation of 4- (4-bromophenoxy) tetrahydro-2H-pyran (compound of formula 18-2) 4-bromophenol (Formula 18-1, 500 mg, 2.89 mmol),After 4-hydroxytetrahydropyran (0.4 ml, 4.34 mmol, 1.5 eq) and triphenylphosphine (PPh3) (1.1 g, 4.34 mmol, 1.5 eq) were dissolved in toluene (8 ml), diethyl azodica Foxylate (DEAD) (1.4 ml, 3.18 mmol, 1.1 eq) was added dropwise at 0 ° C. The reaction mixture was stirred at room temperature for 45 minutes. After completion of the reaction, the solvent was removed under reduced pressure, dissolved in diethyl ether, and the resulting solid was filtered off. Ethyl acetate was added to the filtrate, washed with H 2 O, dried over anhydrous MgSO 4 and the solvent was removed under reduced pressure. Then, the reaction mixture was separated and purified by MPLC to obtain the target compound (Formula 18-2). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triphenylphosphine In tetrahydrofuran | 58.a 58a. 58a. 4-(4-Bromo-phenoxy)-tetrahydropyran A mixture of 4.0 mL of diethyl-azodicarboxylate in 20 mL of dry tetrahydrofuran was added at 5° C. to a stirred solution of 3.5 g of 4-bromo-phenol, 2.4 mL of 4-hydroxy-tetrahydropyran and 6.6 g triphenylphosphine in 75 mL of tetrahydrofuran within 30 minutes. Stirring was continued at room temperature for 72 hours. The solvent was evaporated in vacuo and the residue chromatographed on silica gel (ethyl acetate) yielding 5.6 g of 4-(4-bromo-phenoxy)-tetrahydropyran as a white solid. M.p. 53-55° C., EI-MS: 256 (M+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triphenylphosphine In tetrahydrofuran; ethyl acetate | R.80 Reference Example 80 Reference Example 80 To a solution of 4-bromophenol (15.0 g), tetrahydropyran-4-ol (9.Og) and triphenylphosphine (23.08 g) in THF (100 ml) was added dropwise at 0° C. diethyl azodicarboxylate (40% toluene solution) (38.3 g), and the mixture was stirred at room temperature for 3 days and concentrated under reduced pressure. To the residue was added diethylether, and precipitated crystals were removed by filtration. The filtrate was concentrated, and the residue was dissolved in ethyl acetate. The solution was washed with 1N sodium hydroxide solution (*3) and saturated brine, dried with magnesium sulfate and concentrated under reduced pressure. The residue was purified with silica gel column chromatography (ethyl acetate/hexane=1:4) to give colorless crystals of 4-(4-bromophenyloxy)tetrahydropyran (15.94 g). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; n-butyllithium In tetrahydrofuran; hexane | R.80 Reference Example 80 To a solution of 4-(4-bromophenyloxy)tetrahydropyran (15.73 g) in THF (100 ml) was added dropwise at -78° C. a solution of 1.6M n-butyllithium in hexane (42 ml), and the mixture was stirred for 1 hour. To the mixture was added dropwise a solution of trimethyl borate (20 ml) in THF (20 ml) for 1 hour, and the mixture was stirred at -78° C. for 1 hour. The reaction mixture was allowed to warm to room temperature, and the mixture was stirred at room temperature for 2 hours. To the mixture was added dropwise 1N hydrochloric acid (100 ml), and the mixture was stirred for 1 hour and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and dried with magnesium sulfate. The solvent was evaporated under reduced pressure to give colorless crystals, which were collected by filtration and washed with ethyl acetate/hexane to give colorless crystals of 4-(tetrahydropyran-4-yloxy)phenyl borate (4.30 g). The mother liquor was purified with silica gel column chromatography (ethyl acetate/hexane=1:1) to give colorless crystals of 4-(tetrahydropyran-4-yloxy)phenyl borate (2.97 g). 1H-NMR (200 MHz, CDCl3) δ 1.74-1.93 (2H, m), 1.98-2.15 (2H, m), 3.55-3.68 (2H, m), 3.95-4.08 (2H, m), 4.56-4.70 (1H, m), 7.02 (2H, d, J=8.6 Hz), 8.15 (2H, d, J=8.6 Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With n-butyllithium; sulfuryl dichloride In tetrahydrofuran; hexane | 58.b 58b. 58b. 4-(Tetrahydropyran-4-yloxy)-benzenesulfonyl chloride To a solution of 2.8 g of 4-(4-Bromo-phenoxy)-tetrahydropyran in 75 mL of dry tetrahydrofuran was added 7.5 mL of n-butyllithium (1.6 N in hexane) at -78° C. After stirring at -78° C. for 2 hours the reaction mixture was allowed to warm to -40° C. and a solution of 4.1 mL of sulfuryl chloride in 75 mL of dry hexane was added within 15 minutes. Stirring was continued for 1 hour at -30° C. and subsequently for another hour at 5° C. The mixture was poured on ice, extracted with diethyl ether and the ether extract washed with cold water and brine, dried (sodium sulfate), and concentrated. The residue was purified by silica chromatography (isohexane/ethyl acetate 4/1) yielding 0.62 g of 4-(tetrahydropyran-4-yloxy)-benzenesulfonyl chloride as a colorless oil. EI-MS: 276 (M+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | Stage #1: 4-(4-bromo-phenoxy)-tetrahydropyran With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1.5h; Stage #2: 2,3,4,6-tetra-O-benzyl-1-C-(3-formylphenyl)-5-thio-D-glucopyranose In tetrahydrofuran for 3h; Stage #3: With water; ammonium chloride In tetrahydrofuran | 13 Example 13 [Show Image] Synthesis of (1S)-1,5-anhydro-2,3,4,6-tetra-O-benzyl-1-[3-[4-(4-tetrahydropyranyloxy)benzyl]phenyl]-1-thio-D-glucitol; 2.6 M n-butylithium hexane solution (0.8 mL) was added to a mixture of 1-bromo-4-(4-tetrahydropyranyloxy)benzene (0.545 g, 2.12 mmol) and tetrahydrofuran (6 mL) at -78°C. After stirred for 1.5 hours, a tetrahydrofuran (8 mL) solution of 2,3,4,6-tetra-O-benzyl-1-C-(3-formylphenyl)-5-thio-D-glucopyranose(0.70 g, 1.06 mmol) was added and further stirred for three hours, and the reaction mixture was warmed to room temperature. After the reaction mixture was added with a saturated ammonium chloride aqueous solution and extracted with ethyl acetate, the organic phase was washed with brine and dried with anhydrous magnesium sulfate. After the desiccant was filtered off, the residue obtained by evaporating the solvent under reduced pressure was purified by silica gel column chromatography (hexane:ethyl acetate =2:1) to obtain 2,3,4,6-tetra-O-benzyl-1-C-[3-[(4-(4-tetrahydropyranyloxy)phenyl)(hydroxy)methyl]phenyl]-5-thio-D-glucopyranose (0.67 g, 76%). Then, an acetonitrile (8 mL) solution of 2,3,4,6-tetra-O-benzyl-1-C-[3-[(4-(4-tetrahydropyranyloxy)phenyl)(hydroxy)methyl]phenyl]-5-thio-D-glucopyranose (0.67 g, 0.802 mmol) was added sequentially with Et3SiH (0.78 mL, 4 . 90 mmol) and BF3-Et2O (0.41 mL, 3.27 mmol) at -15°C. After stirred for one hour, the reaction mixture was warmed up to room temperature and stirred for three hours. After the reaction mixture was added with a saturated sodium carbonate aqueous solution and extracted with ethyl acetate, the organic layer was washed with brine and dried with anhydrous magnesium sulfate. After the desiccant was filtered off, the residue obtained by evaporating the solvent under reduced pressure was purified by silica gel column chromatography (hexane:ethyl acetate =4:1) to obtain a colorless powdered title compound (0.37 g, 57%). 1H NMR (300 MHz, CHLOROFORM-d) δ ppm 1.66 - 1.81 (m, 2 H) 1.88-2.02 (m, 2 H) 3.05 - 3.15 (m, 1 H) 3.47 - 3.59 (m, 3 H) 3.64 - 4.00 (m, 10 H) 4.33 - 4.42 (m, 1 H) 4.46 (d, J=9.95 Hz, 1 H) 4.52 (s, 2 H) 4.60 (d, J=10.41 Hz, 1 H) 4.84 - 4.93 (m, 3 H) 6.60 - 6.67 (m, 2 H) 6.72 - 6.79 (m, 2 H) 6.99 - 7.19 (m, 8 H) 7.20 - 7.35 (m, 16 H). ESI m/Z = 824(M+NH4). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In N,N-dimethyl-formamide at 125℃; for 5h; Inert atmosphere; | A General Method E (Borylation of aryl halides): using B^pm? / Pd General procedure: A mixture of aryliodide or arylbromide (1 equiv.), bis(pinacolato)diboron (1.2 to 1.5 equiv.), OAc (3 equiv.) and DMF or DMSO was purged with Ar for 10 min. [1,1'- PdCl2dppf*CH2Cl2 (3-5 mol%) was added, the vial sealed and heated at 85-100 °C for 2-3 h. The product was partitioned between EtOAc and satd aq NaHC03 solution, washed with brine, dried over Na2S04 or MgS0 , filtered, and concentrated to dryness. The crude product was purified by flash chromatography to give the title compound. |
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In 1,4-dioxane at 100℃; for 12h; | 18.2 Step 2: Preparation of 4,4,5,5-tetramethyl-2-(4-(tetrahydro-2H-pyran-4-yloxy)phenyl)-1,3,2-dioxaborolane (compound of formula 18-3) Step 2: 4,4,5,5-tetramethyl-2- (4- (tetrahydro-2H-pyran-4-yloxy) phenyl) -1,3,2-dioxaborolane (Formula 18-3 Preparation of the compound4- (4-Bromophenoxy) tetrahydro-2H-pyran synthesized in Step 1 (Formula 18-2, 638 mg, 2.48 mmol), potassium acetate (731 mg, 7.44 mmol, 3 eq), Pd (dppf ) Cl2-CH2Cl2 (203 mg, 0.25 mmol, 0.1 eq) and B2Pin2 (756 mg, 2.98 mmol, 1.2 eq) were dissolved in 1,4-dioxane (15 ml). The temperature was raised to 100 ° C and the reaction mixture was stirred for 12 hours. After completion of the reaction, the reaction mixture was filtered through celite and extracted with ethyl acetate. The organic layer was washed with H 2 O, dried over anhydrous MgSO 4, and the solvent was removed under reduced pressure. Then, the reaction mixture was separated and purified by MPLC (hexane / ethyl acetate) to give the target compound (Formula 18-3). | |
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In 1,4-dioxane at 100℃; for 12h; | 18.2 Step 2: 4,4,5,5-tetramethyl-2- (4- (tetrahydro-2H-pyran-4-yloxy) phenyl) -1,3,2-dioxaborolane (Formula 18-3 Preparation of compounds) 4- (4-Bromophenoxy) tetrahydro-2H-pyran synthesized in step 1 (Formula 18-2, 638 mg, 2.48 mmol), potassium acetate (731 mg, 7.44 mmol, 3 eq), Pd (dppf ) Cl2-CH2Cl2 (203 mg, 0.25 mmol, 0.1 eq) and B2Pin2 (756 mg, 2.98 mmol, 1.2 eq) were dissolved in 1,4-dioxane (15 ml). The reaction mixture was stirred for 12 hours by raising the temperature to 100 ° C.After completion of the reaction, the reaction mixture was filtered through celite, and extracted with ethyl acetate. The organic layer was washed with H 2 O, then dried over anhydrous MgSO 4 and the solvent was removed under reduced pressure. Then, the reaction mixture was separated and purified by MPLC (hexane / ethyl acetate) to obtain the target compound (Formula 18-3). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triphenylphosphine; diethylazodicarboxylate In toluene for 0.5h; | Intermediate 8: 4-(4-bromo-2-fluoro-phenoxy)tetrahydropyran General procedure: Intermediate 8: 4-(4-bromo-2-fluoro-phenoxy)tetrahydropyran. [0219] A solution of tetrahydropyran-4-ol (914 mg, 8.96 mmol), 4-bromo-2-fluoro- phenol (1.926 g, 10.0 mmol) and PPh3 (2.588 g, 9.9 mmol) in toluene (30 mL) was treated with diethyl azodicarboxylate (40 wt% in toluene, 5 mL, 10 mmol) and stirred for 30 min. The reaction was diluted with EtOAc, washed with H20 and brine, dried (MgS04), filtered and concentrated. Purification by two MPLC columns (Si02, EtOAc/Hexanes, 0 - 50%) provided the title compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: lithium hexamethyldisilazane; DavePhos; palladium diacetate / toluene / 4 h / -78 - 80 °C / Schlenk technique 2: lithium bromide; potassium hydrogen difluoride / dichloromethane; water / 24 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: lithium hexamethyldisilazane; DavePhos; palladium diacetate / toluene / 4 h / -78 - 80 °C / Schlenk technique 2.1: potassium <i>tert</i>-butylate / toluene / 0.17 h / 20 °C / Schlenk technique; Inert atmosphere 2.2: 1 h / Inert atmosphere; Schlenk technique |
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