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CAS No. : | 1260007-55-3 | MDL No. : | MFCD18207826 |
Formula : | C10H8BrFO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | IYENTJQOLSXUQB-UHFFFAOYSA-N |
M.W : | 243.07 | Pubchem ID : | 71299217 |
Synonyms : |
|
Num. heavy atoms : | 13 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.3 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 51.95 |
TPSA : | 17.07 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) : | -5.79 cm/s |
Log Po/w (iLOGP) : | 2.21 |
Log Po/w (XLOGP3) : | 2.81 |
Log Po/w (WLOGP) : | 3.53 |
Log Po/w (MLOGP) : | 3.12 |
Log Po/w (SILICOS-IT) : | 4.06 |
Consensus Log Po/w : | 3.15 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.46 |
Solubility : | 0.0845 mg/ml ; 0.000348 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.83 |
Solubility : | 0.363 mg/ml ; 0.00149 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -4.53 |
Solubility : | 0.00712 mg/ml ; 0.0000293 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.21 |
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 |
---|---|---|
Multi-step reaction with 2 steps 1.1: titanium(IV) isopropylate / methanol; isopropyl alcohol / 16 h / 35 °C 1.2: 1 h / 20 °C 1.3: 0.5 h / 20 °C 2.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate / 1,4-dioxane / 16 h / 100 °C / Sealed tube; Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: sodium cyanoborohydride; ammonium acetate / isopropyl alcohol / 16 h / 70 °C 1.2: 0.5 h / 20 °C 2.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate / 1,4-dioxane / 16 h / 100 °C | ||
Multi-step reaction with 2 steps 1.1: sodium cyanoborohydride; ammonium acetate / isopropyl alcohol / 16 h / 70 °C 1.2: 0.5 h / 20 °C 2.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate / 1,4-dioxane / 16 h / 100 °C / Sealed tube; Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | Stage #1: 5-bromo-6-fluoro-3,4-dihydronaphthalen-1(2H)-one; methylamine With titanium(IV) isopropylate In methanol; isopropyl alcohol at 35℃; for 16h; Stage #2: With methanol; sodium tetrahydroborate In isopropyl alcohol at 20℃; for 1h; Stage #3: di-<i>tert</i>-butyl dicarbonate In dichloromethane at 20℃; for 0.5h; | 120.1 Step 1. tert-Butyl 5-bromo-6-fluoro-1,2,3,4-tetrahydronaphthalen-1-yl(methyl)carbamate To a solution of 5-bromo-6-fluoro-3,4-dihydronaphthalen-1(2H)-one (Ark Pharm, 312.6 mg, 1.286 mmol) in 2-propanol (10.0 ml) was added methylamine (2.0 M in methanol) (2.50 ml, 5.00 mmol) followed by titanium(IV) isopropoxide (596.0 mg, 2.097 mmol). The mixture was stirred at 35° C. for 16 h before it was cooled to room temperature. Sodium borohydride (53.4 mg, 1.412 mmol) was added. The reaction was stirred at room temperature for 1 h, and was treated with HCl (1.0 N in water) (30.0 ml, 30 mmol). The mixture was stirred at room temperature for 2 h, and was treated with NaOH (4.0 N in water) until the pH reached 10. The mixture was extracted with Et2O. The organic phase was separated, dried over anhydrous Na2SO4, filtered and concentrated. The residue was dissolved in CH2Cl2 (10 ml), and treated with boc-anhydride (426.4 mg, 1.954 mmol). After stirring at room temperature for 30 min, the reaction was concentrated. The residue was purified on silica gel (40 g, 0-100% EtOAc in hexanes) to give the desired product (461.0 mg, 89%). LCMS calculated for C12H14BrFNO2 (M+H-C4H8)+: m/z=302.0; found: 302.1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | Stage #1: 5-bromo-6-fluoro-3,4-dihydronaphthalen-1(2H)-one With ammonium acetate; sodium cyanoborohydride In isopropyl alcohol at 70℃; for 16h; Stage #2: di-<i>tert</i>-butyl dicarbonate In dichloromethane at 20℃; for 0.5h; | 121.1 Step 1. tert-Butyl 5-bromo-6-fluoro-1,2,3,4-tetrahydronaphthalen-1-ylcarbamate To a mixture of 5-bromo-6-fluoro-3,4-dihydronaphthalen-1(2H)-one (Ark Pharm, 309.5 mg, 1.273 mmol), sodium cyanoborohydride (824.0 mg, 13.11 mmol) and ammonium acetate (2.184 g, 28.3 mmol) was added 2-propanol (10.0 ml). The reaction was stirred at 70° C. for 16 h. After cooling to room temperature, the mixture was diluted with 2 M K2CO3 (aq) and extracted with Et2O. The organic phase was separated, was dried over anhydrous Na2SO4, filtered and concentrated. The residue was dissolved in CH2Cl2 (20 ml), and was treated with Boc-anhydride (425.9 mg, 1.951 mmol). After stirring at room temperature for 30 min, the reaction mixture was concentrated. The residue was purified on silica gel (40 g, 0-100% EtOAc in hexanes) to give the desired product as a white solid (316.3 mg, 72%). LCMS calculated for C11H12BrFNO2 (M+H-C4H8)+: m/z=288.0; found: 288.0. |
72% | Stage #1: 5-bromo-6-fluoro-3,4-dihydronaphthalen-1(2H)-one With ammonium acetate; sodium cyanoborohydride In isopropyl alcohol at 70℃; for 16h; Stage #2: di-<i>tert</i>-butyl dicarbonate In dichloromethane at 20℃; for 0.5h; | 241.1 Step 1. tert-Butyl 5-bromo-6-fluoro-1,2,3,4-tetrahydronaphthalen-1-ylcarbamate To a mixture of 5-bromo-6-fluoro-3,4-dihydronaphthalen-1(2H)-one (Ark Pharm, 309.5 mg, 1.273 mmol), sodium cyanoborohydride (824.0 mg, 13.11 mmol) and ammonium acetate (2.184 g, 28.3 mmol) was added 2-propanol (10.0 ml). The reaction was stirred at 70° C. for 16 h. After cooling to room temperature, the mixture was diluted with 2 M K2CO3 (aq) and extracted with Et2O. The organic layer was dried over anhydrous Na2SO4, filtered and concentrated. The residue was dissolved in CH2Cl2 (20 ml), and was treated with Boc-anhydride (425.9 mg, 1.951 mmol). After stirring at room temperature for 30 min, the reaction was concentrated. The residue was purified on silica gel (40 g, 0-100% EtOAc in hexanes) to give the desired product as a white solid (316.3 mg, 72%). LCMS calculated for C11H12BrFNO2 (M+H-C4H8)+: m/z=288.0; found: 288.0. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: titanium(IV) isopropylate / isopropyl alcohol; methanol / 16 h / 35 °C 1.2: 1 h / 20 °C 1.3: 0.5 h / 20 °C 2.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate / 1,4-dioxane / 16 h / 100 °C / Sealed tube; Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | Stage #1: 5-bromo-6-fluoro-3,4-dihydronaphthalen-1(2H)-one; methylamine With titanium(IV) isopropylate In methanol; isopropyl alcohol at 35℃; for 16h; Stage #2: With methanol; sodium tetrahydroborate In isopropyl alcohol at 20℃; for 1h; Stage #3: With di-<i>tert</i>-butyl dicarbonate In dichloromethane at 20℃; for 0.5h; | 208.1; 240.1 Step 1. tert-Butyl 5-bromo-6-fluoro-1,2,3,4-tetrahydronaphthalen-1-yl(methyl)carbamate To a solution of 5-bromo-6-fluoro-3,4-dihydronaphthalen-1(2H)-one (Ark Pharm, 352.6 mg, 1.451 mmol) in 2-propanol (10.0 ml) was added methylamine (2.0 M in methanol) (2.50 ml, 5.00 mmol) followed by titanium(IV) isopropoxide (596.0 mg, 2.097 mmol). The mixture was stirred at 35° C. for 16 h before it was cooled to room temperature. Sodium borohydride (53.4 mg, 1.412 mmol) was added. The reaction mixture was stirred at room temperature for 1 h, and was quenched with HCl (1.0 N in water) (30.0 ml, 30 mmol). The mixture was stirred at room temperature for 2 h, and was treated with NaOH (4.0 N in water) until pH reached 10. The mixture was extracted with Et2O. The organic layer was dried over anhydrous Na2SO4, filtered and concentrated. The residue was dissolved in CH2Cl2 (10 ml), and treated with Boc-anhydride (426.4 mg, 1.954 mmol). After stirring at room temperature for 30 min, the reaction mixture was concentrated. The residue was purified on silica gel (40 g, 0-100% EtOAc in hexanes) to give the desired product (461.0 mg, 89%). LCMS calculated for C12H14BrFNO2 (M+H-C4H8)+: m/z=302.0; found: 302.1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: triethylamine / 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran / 2 h / 0 - 25 °C / Inert atmosphere 2: palladium diacetate; oxygen / dimethyl sulfoxide / 16 h / 35 °C / 775.74 Torr |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: triethylamine / 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran / 2 h / 0 - 25 °C / Inert atmosphere 2: palladium diacetate; oxygen / dimethyl sulfoxide / 16 h / 35 °C / 775.74 Torr 3: water; methanol / 12 h / 25 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: triethylamine / 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran / 2 h / 0 - 25 °C / Inert atmosphere 2: palladium diacetate; oxygen / dimethyl sulfoxide / 16 h / 35 °C / 775.74 Torr 3: water; methanol / 12 h / 25 °C 4: potassium carbonate / N,N-dimethyl-formamide / 16 h / 25 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: triethylamine / 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran / 2 h / 0 - 25 °C / Inert atmosphere 2: palladium diacetate; oxygen / dimethyl sulfoxide / 16 h / 35 °C / 775.74 Torr 3: water; methanol / 12 h / 25 °C 4: potassium carbonate / N,N-dimethyl-formamide / 16 h / 25 °C 5: potassium carbonate; tert-butyl XPhos; bis(η3-allyl-μ-chloropalladium(II)) / 2-methyltetrahydrofuran / 12 h / 80 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine In 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran at 0 - 25℃; for 2h; Inert atmosphere; | 221.1 Step 1: ((5 -Bromo-6-fluoro-3 ,4-dihydronaphthalen- 1 -yl)oxy)trimethylsilane To a solution of 5-bromo-6-fluoro-tetralin-1-one (5.0 g, 20.57 mmol) and triethylamine (11.56 mL, 82.28 mmol) in anhydrous dichloromethane (50 mL) was added trimethylsilyl trifluoromethanesulfonate (7.45 mL, 41.14 mmol) dropwsie at 0 °C under nitrogen atmosphere. The reaction mixture was stirred at 25 °C for 2 h. The reaction was then quenched with ice water (50 mL) and extracted with methyl tert butyl ether (50 mL). The organic layer was separated, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to yield 6.4 g (crude) of the title compound as a yellow oil. |
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