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CAS No. : | 1189042-70-3 | MDL No. : | MFCD15143593 |
Formula : | C12H15BFNO4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | RNRPIYYFOPOLSL-UHFFFAOYSA-N |
M.W : | 267.06 | Pubchem ID : | 51034464 |
Synonyms : |
|
Num. heavy atoms : | 19 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.5 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 5.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 71.7 |
TPSA : | 64.28 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | Yes |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | Yes |
Log Kp (skin permeation) : | -5.91 cm/s |
Log Po/w (iLOGP) : | 0.0 |
Log Po/w (XLOGP3) : | 2.84 |
Log Po/w (WLOGP) : | 2.45 |
Log Po/w (MLOGP) : | 1.05 |
Log Po/w (SILICOS-IT) : | 0.09 |
Consensus Log Po/w : | 1.29 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.39 |
Solubility : | 0.11 mg/ml ; 0.000411 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.85 |
Solubility : | 0.0379 mg/ml ; 0.000142 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.66 |
Solubility : | 0.0587 mg/ml ; 0.00022 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 3.0 alert |
Leadlikeness : | 0.0 |
Synthetic accessibility : | 3.09 |
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: |
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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 |
---|---|---|
With potassium fluoride; tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine In tetrahydrofuran; 1,4-dioxane at 20 - 50℃; for 1.5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
488 mg | With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 90℃; for 16h;Inert atmosphere; Sealed tube; | Step A: Synthesis of 2-(2-fluoro-3-nitrophenyl)-4,4,5,5-tetramethyl-l,3,2-dioxaborolane Compound l-bromo-2-fluoro-3 -nitrobenzene (440 mg) was dissolved in 10 mL of dry 1,4-dioxane. To this was added potassium acetate, followed by bis(pinacolato)diboron (759 mg). Nitrogen was bubbled through the reaction vessel for 1 min and PdCl2(dppf) (164 mg) was added. The reaction mixture was sealed and heated to 90 C for 16 h, then cooled to room temperature and poured into water and extracted with ethyl acetate three times. The combined organic layers were dried over sodium sulfate, filtered and concentrated under vacuum to give the title compound (488 mg). NMR (300 MHz, CDC13): delta 1.37 (s, 12H), 7.27 (m, 1H), 7.99 (m, 1H), 8.09 (m, 1H). |
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 80℃; for 16h;Inert atmosphere; | General Procedure Synthesis of (41a) To a mixture of <strong>[58534-94-4]1-bromo-2-fluoro-3-nitrobenzene</strong> (1.4 mmol) in dioxane (10 mL) was added 4,4,5,5-tetramethyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3,2-dioxaborolane (1.5 eq) and KOAc (2 eq), and Pd(dppf)Cl2 (0.1 eq). The mixture was degassed and purged with N2 for 3 times. The mixture was stirred at 80 C. for 16 hours and was poured into water and extracted with ethyl acetate 3 times. The combined organic layers were washed with brine, dried with anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was purified by column chromatography (SiO2, Petroleum ether/Ethyl acetate=15:1 to 10:1) to give 2-(2-fluoro-3-nitrophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (41a). 1H NMR (400 MHz, DMSO) delta 13.47 (br s, 1H), 8.03-6.96 (m, 4H), 2.20 (s, 3H), 1.94-1.77 (m, 1H), 0.80 (br s, 2H), 0.70 (br s, 2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogen;palladium 10% on activated carbon; In ethyl acetate; under 760.051 Torr; for 16h; | [00202] Intermediate. 2-fluoro-3-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2- yl) aniline:[00203] A mixture of Intermediate 2-(2-fluoro-3-nitrophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (500 mg), 10% palladium on carbon (50 mg) and ethyl acetate (20 ml) was stirred under 1 atmosphere of hydrogen for 16 h. The mixture was sparged with nitrogen and filtered. The filtrate was concentrated to provide the title compound, which was used without further purification. MS m/z 237.1 (M + 1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In 1,4-dioxane; water; at 120℃; for 1h;microwave irradiation; | To a solution of <strong>[96424-68-9]2-bromo-3-chloropyridine</strong> [96424-68-9] (144 mg, 0.75 mmol) and 2-fluoro-3- nitrophenylboronic acid pinacol ester [1 189042-70-3] (200 mg, 0.75 mmol) in dioxane (4 mL) and water (1 mL) was added potassium carbonate (259 mg, 1.87 mmol) and Pd(dppf)CI2 CH2CI2 adduct (61.2 mg, 0.075 mmol). The solution was heated for 60 min at 120C under microwave irradiation. The reaction mixture was diluted with EtOAc and the resulting solution was washed successively with saturated aqueous NaHC03 solution and brine, then dried (Phase separator) and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (c-hexane/EtOAc 4:1) to give the title compound. MS (LC-MS): 253 [M+H]+; tR (HPLC conditions k): 3.45 min. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
400 mg | With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In 1,2-dimethoxyethane; water for 1h; Reflux; Inert atmosphere; | B Step B: Synthesis of 2-(3,5-dichlorophenyl)-5-(2-fluoro-3-nitrophenyl)-2-(trifluoromethyl)-2,3- dihydrobenzofuran Step B: Synthesis of 2-(3,5-dichlorophenyl)-5-(2-fluoro-3-nitrophenyl)-2-(trifluoromethyl)-2,3- dihydrobenzofuran Under the protection of nitrogen, compound 2-(3,5-dichlorophenyl)-5-iodo-2- (trifluoromethyl)-2,3-dihydrobenzofuran (458 mg), PdCl2(dppf) (80 mg), potassium carbonate (414 mg) and compound 2-(2-fluoro-3-nitrophenyl)-4,4,5,5-tetramethyl-l,3,2-dioxaborolane (400 mg) were dissolved in 20 mL of DME and 10 mL of H20. After the addition, the mixture was refluxed for 1 h. Then, it was filtered through silica gel, and concentrated under vacuum. The residue was purified by column chromatography on silica gel to give the title compound (400 mg). NMR (300 MHz, OMSO-d6): δ 3.92 (d, 1H), 4.10 (d, 1H), 7.27 (d, 1H), 7.45-7.52 (m, 3H), 7.73 (s, 2H), 7.78 (s, 1H), 7.86 (t, 1H), 8.10 (t, 1H |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In 1,4-dioxane at 25 - 80℃; for 16h; Inert atmosphere; | S.26 Synthesis of (41b) Synthesis of (41b) To a mixture of 2-(2-fluoro-3-nitrophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (41a) (0.86 mmol) and 5-bromo-1H-imidazole (1.5 eq) in dioxane (10 mL) was added Pd(dppf)Cl2.CH2Cl2 (0.1 eq), (Boc)2O (2 eq) and KOAc (3 eq) at 25° C. under N2. The mixture was stirred at 80° C. for 16 hours. LC-MS showed desired MS was detected. The residue was poured into water and the mixture was extracted with ethyl acetate. The organic phase was washed with brine, dried with anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was purified by prep-TLC (SiO2, Petroleum ether:Ethyl acetate=3:1) to give tert-butyl 5-(2-fluoro-3-nitrophenyl)-1H-imidazole-1-carboxylate (41b). MS mass calculated for [M+1]+ (C14H14FN3O4) requires m/z 306.1, LCMS found m/z 207.9. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate; In 1,4-dioxane; at 25 - 110℃; for 12.0h;Inert atmosphere; | Tert-butyl 5-(2-fluoro-3-nitrophenyl)-4-methyl-1H-imidazole-1-carboxylate (51b) To a mixture of <strong>[15813-08-8]5-bromo-4-methyl-1H-imidazole</strong> (200 mg, 1.24 mmol), 2-(2-fluoro-3-nitrophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (663.51 mg, 2.48 mmol) (51a) and Boc2O (1.08 g, 4.97 mmol, 1.14 mL) in 1,4-dioxane (10 mL) was added Pd(dppf)Cl2-CH2Cl2 (101.45 mg, 124.22 umol) and K2CO3 (343.37 mg, 2.48 mmol) at 25 C. under N2. The mixture was stirred at 110 C. for 12 hours. The reaction mixture was filtered and the filtrate was concentrated in vacuo. The residue was diluted with H2O (10 mL) and extracted with ethyl acetate (10 mL). The organic layer was washed with brine (8 mL*2), dried with anhydrous Na2SO4, filtered and concentrated under reduced pressure. The crude product was purified by prep-TLC (SiO2, DCM:MeOH=10:1) to give tert-butyl 5-(2-fluoro-3-nitrophenyl)-4-methyl-1H-imidazole-1-carboxylate (51b). 1H NMR (400 MHz, CHLOROFORM-d) delta=8.21-8.13 (m, 1H), 8.06-7.98 (m, 1H), 7.89-7.81 (m, 1H), 7.40-7.29 (m, 1H), 2.51-2.41 (m, 3H), 1.66 (s, 9H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate In 1,4-dioxane at 90℃; for 16h; Inert atmosphere; | S.42 4-bromo-5-(2-fluoro-3-nitrophenyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole (74a) 4-bromo-5-(2-fluoro-3-nitrophenyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole (74a) To a mixture of 2-(2-fluoro-3-nitrophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (51a) (476.94 mg, 1.79 mmol) and 4,5-dibromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole (530 mg, 1.49 mmol) in dioxane (12 mL) was added K2CO3 (617.06 mg, 4.46 mmol) and Pd(dppf)Cl2 CH2Cl2 (121.53 mg, 148.82 umol) under N2. The mixture was stirred at 90° C. for 16 hours. The reaction mixture was concentrated under reduced pressure to remove most of the dioxane, the residue was poured into water (10 mL) and extracted with ethyl acetate (20 mL*3). The combined organic layers were washed with brine (15 mL*2), and dried with anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was purified by column chromatography (SiO2, Petroleum ether:Ethyl acetate=50:1 to 5:1) to give 74a. MS mass calculated for [M+1]+ (C15H19BrFN3O3Si) requires m/z, 415.1/417.1, LCMS found m/z 416.1/418.1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
2.3 g | Stage #1: 2-(2-fluoro-3-nitrophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane; tert-butyl ((3-bromo-1-methyl-1H-pyrazol-4-yl)methyl)(methyl-d3)carbamate With potassium fluoride In tetrahydrofuran for 0.25h; Inert atmosphere; Stage #2: With dicyclohexyl({2’,6’-dimethoxy-[1,1‘-biphenyl]-2-yl})phosphane; palladium diacetate In tetrahydrofuran at 70℃; for 16h; Inert atmosphere; Sealed tube; | 8.4 Step-4: tert-butyl ((3-(2-fluoro-3-nitrophenyl)-l-methyl-lH-pyrazol-4-yl)methyl)(methyl-d3)carbamate (I-8e) Argon gas was purged through a stirred suspension of I-8d (2.5 g, 8.14 mmol), 2-(2-fluoro-3-nitrophenyl)-4,4,5,5-tetramethyl-l,3,2-dioxaborolane (3.26 g, 12.2 mmol) and KF (1.42 g, 24.4 mmol) in THF (40.0 mL) for 15 min. To this was then added Pd(OAc)2 (0.0914 g, 0.407 mmol) and dicyclohexyl({2',6'-dimethoxy-[l,l'-biphenyl]-2-yl})phosphane (0.334 g, 0.814 mmol). The reaction mixture was then stirred at 70 °C for 16 h in a sealed tube. It was then cooled to room temperature, filtered through celite bed and washed with EtOAc (50 mL x 2). The combined filtrate was concentrated under reduced pressure and the residue was purified by Combi-Flash (using gradient elution of 0-30% EtOAc in hexane) to afford tert-butyl ((3-(2-fluoro-3-nitrophenyl)-l-methyl-lH-pyrazol-4-yl)methyl)(methyl-d3)carbamate I-8e (2.3 g) as a yellow oil. LCMS (ES) m/z 368.2 [M+H]+. |
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