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CAS No. : | 90841-46-6 | MDL No. : | MFCD11227152 |
Formula : | C10H11BrO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | HBAMBTOWPNCADR-UHFFFAOYSA-N |
M.W : | 243.10 | Pubchem ID : | 23134395 |
Synonyms : |
|
Num. heavy atoms : | 13 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.3 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 55.35 |
TPSA : | 26.3 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) : | -5.48 cm/s |
Log Po/w (iLOGP) : | 2.7 |
Log Po/w (XLOGP3) : | 3.24 |
Log Po/w (WLOGP) : | 2.85 |
Log Po/w (MLOGP) : | 3.25 |
Log Po/w (SILICOS-IT) : | 3.33 |
Consensus Log Po/w : | 3.07 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.6 |
Solubility : | 0.0614 mg/ml ; 0.000252 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.47 |
Solubility : | 0.0832 mg/ml ; 0.000342 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -4.11 |
Solubility : | 0.019 mg/ml ; 0.0000782 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.67 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302 | 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 |
---|---|---|
With triethylamine;palladium diacetate; 1,3-bis-(diphenylphosphino)propane; In dimethyl sulfoxide; at 75℃; | Reference Example 24; Methyl 4-bromo-2,6-dimethylbenzoate; Trifluoromethanesulfonic anhydride (1.004mL) was added to an ice-cooled mixture of 4-bromo-2,6-dimethylphenol (1.00g) and pyridine (0.482mL) in methylene chloride (5mL) with stirring. After being stirred for 10minutes, the reaction mixture was poured into a mixture of 1mol/L hydrochloric acid and ethyl acetate. The organic layer was separated, washed with water and brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: diethyl ether/n-hexane=1/20) to afford 4-bromo-2,6-dimethylphenyl trifluoromethanesulfonate (1.439g). A mixture of 4-bromo-2,6-dimethylphenyl trifluoromethanesulfonate (1.439g), palladium acetate (0.049g), 1,3-bis(diphenylphosphino)propane (0.089g) and triethylamine (1.336mL) in methanol (10mL)/dimethylsulfoxide (15mL) was stirred at 75 C overnight under an atmosphere of carbon monoxide. Water and ethyl acetate were added to the reaction mixture. The organic layer was separated, washed with water and brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/5) to afford the title compound (0.435g). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 1.5h; | [0161] To a stirred solution of <strong>[74346-19-3]4-bromo-2,6-dimethylbenzoic acid</strong> (2.81 g, 12.3 mmol) in DMF (30 mL) was added iodomethane (2.30 mL, 36.9 mmol) and potassium carbonate (5.09 g, 36.9 mmol) and reaction was stirred at room temperature for 1.5 hours. The reaction mixture was partitioned between water and ethyl acetate and the organic layer was washed with brine. The solvent was removed under reduced pressure to yield an amber oil (3.06g). -lK NMR (300 MHz, CDC13): 6 7.22 (S, 2H), 3.92 (s, 3H), 2.30 (s, 6H). | |
With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 1.5h; | To a stirred solution of <strong>[74346-19-3]4-bromo-2,6-dimethylbenzoic acid</strong> (2.81 g, 12.3 mmol) in dimethylformamide (30 mL) was added iodomethane (2.30 mL, 36.9 mmol) and potassium carbonate (5.09 g, 36.9 mmol) and reaction was stirred at room temperature for 1.5 hours. The reaction mixture was partitioned between water and ethyl acetate and the organic layer was washed with brine. The solvent was removed under reduced pressure to yield an amber oil (3.06g). 1H NMR (300 MHz, CDCl3): delta 7.22 (S, 2H), 3.92 (S) 3H), 2.30 (s, 6H). | |
50.3 g | With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; | Toa solution of 8B (50g, 219 mmol) in DMF (400mL) was added K2C03(48.6 g, 352 mmol) and CH31 (32.7 g, 230 mmol), the mixturewas stirred at room temperature overnight. The reactionwas diluted withwater and extracted with EtOAc. The combinedorganiclayerswere dried overNa2S04,filtered,andevaporatedin vacuum to affordthe crude product which was purified by flash chromatography to afford 8C (50.3 g, 95%) as whitesolid. 1H-NMR (400 MHz, DMSO_d6): 7.19-7.21 (s, 2H), 3.89-3.91(s, 3H), 2.27-2.29(s, 6H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | With caesium carbonate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In dimethyl sulfoxide; at 90℃; for 1h;Inert atmosphere; | As shown in step 6-i of Scheme 6, 2,3-dimethoxy-5-(4,4,5,5-tetramethyl-l,3,2- dioxaborolan-2-yl)pyridine (Compound 2021, 920 mg, 3.47 mmol), methyl 4-bromo-2,6- dimethyl-benzoate (844 mg, 3.47 mmol), and Cs2C03 (2.26 g, 6.94 mmol) were taken up in DMSO (12 mL) in a sealable tube. Nitrogen gas was bubbled through the solution for 5 minutes, dppfPdCl2 (141 mg, 0.174 mmol) added, and the vessel sealed. The reaction mixture was heated at 90C for 60 minutes under an atmosphere of nitrogen. After cooling, the mixture was poured into EtO Ac/water. The organics were washed with water, brine, passed through a plug of Florisil, and concentrated under reduced pressure to give a solid. The solid was suspended in MeOH and collected by filtration to provide methyl 4-(5,6-dimethoxy-3- pyridyl)-2,6-dimethyl-benzoate (Compound 2022, 310 mg). The filtrate was concentrated and purified by silica gel chromatography (0 to 50 % EtO Ac/hex) to provide an additional 400 mg of Compound 2022 (total yield 710 mg, 2.4 mmol, 68% yield). This compound was used in subsequent reactions as is. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With N-Bromosuccinimide; dibenzoyl peroxide; In tetrachloromethane; for 16h;Reflux; | 4-Bromo-2,6-dimethylbenzoate (7.0 g, 28.9 mol) at room temperatureCarbon tetrachloride solutionN-bromosuccinamide (5.14 g, 28.9 mol)And benzoyl peroxide (140 hag, 0.579 ha mole).The reaction solution was refluxed for 16 hours.After the reaction was monitored by TLC, the mixture was cooled to room temperature, filtered and washed with carbon tetrachloride. The filtrate was concentrated to dryness under reduced pressure to give the product as a pale yellow solid (9.2 g, 98% yield). |
With N-Bromosuccinimide; dibenzoyl peroxide; In tetrachloromethane; at 60℃; for 4h; | To a solutionof 8C (50g, 0.22 mol) in CC14 (750 mL)was added N-bromosuccinimide (38.9 g, 0.22 mol) and benzoylperoxide (1.1 g, 4.4 mmol)batchwise. Thereaction mixture was stirredat 60C for 4 hrs. The reaction mixture waswashedwithINNaOHandwater.The organiclayer was dried over Na2S04, filtered, and evaporatedin vacuum to affordcrude 8D (75 g) as a yellowoil. | |
With N-Bromosuccinimide; dibenzoyl peroxide; In tetrachloromethane; for 16h;Reflux; | Synthesis of methyl 4-bromo-2-(bromomethyl)-6-methylbenzoate (2) To a solution of <strong>[90841-46-6]methyl 4-bromo-2,6-dimethylbenzoate</strong> (1, 5.5 g, 22.63 mmol) in carbon tetrachloride at room temperature was add N-bromosuccinamide (4.4 g, 24.89 mmol) and benzoyl peroxide (0.5 g, 2.23 mmol). The reaction was refluxed for 16 h. After completion of the reaction as monitored by TLC, the mixture was cooled to room temperature, filtered and washed with carbon tetrachloride (30 mL). The filtrate was concentrated under reduced pressure to dryness to get methyl 4-bromo-2-(bromomethyl)-6-methylbenzoate (2) as a brown liquid. Yield: 7.5 g, crude; MS (ESI) m/z 322.12 [M+1]+. |
With N-Bromosuccinimide; dibenzoyl peroxide; In tetrachloromethane; at 90℃; for 12h; | To a solution of methyl 4-bromo-2, 6-dimethylbenzoate (5.42 g, 22.3 mmol) in CCl4(80 mL) was added NBS (3.99 g, 22.4 mmol) , and benzoyl peroxide (2.85 g, 11.1 mmol) at room temperature. The mixture was stirred for 12 h at 90 then cooled to room temperature. The solvent was evaporated under reduced pressure and the residue was purified by silica gel flash chromatography, eluting with EtOAc in hexane (0 %to 10 %) to give crude methyl 4-bromo-2- (bromomethyl) -6-methylbenzoate. The residue was re-dissolved in MeOH (15 mL) and NH3.H2O (10 mL) was added. The mixture was stirred for 15 h at room temperature then concentrated under reduced pressure. The residue was purified by silica gel flash chromatography, eluting with EtOAc in hexane (0 %to 40 %) to give the title compound (1.70 g, 34%) . LC-MS (M+H)+= 226.0. | |
With N-Bromosuccinimide; dibenzoyl peroxide; In tetrachloromethane; water; for 20h;Reflux; | A mixture of <strong>[90841-46-6]methyl 4-bromo-2,6-dimethylbenzoate</strong> (24.7 g, 102 mmol), NBS(20.8 g, 117 mmol), BPO (3.28 g, 10.2 mmol, 75 wt. % in H2O), and CCl4 (406 mL) was stirred at reflux for 20 h. Upon cooling, H2O (100 mL) and brine (100 mL) were added. The organic phase was dried over Na2S04, concentrated, and taken crude into the next step. |
Tags: 90841-46-6 synthesis path| 90841-46-6 SDS| 90841-46-6 COA| 90841-46-6 purity| 90841-46-6 application| 90841-46-6 NMR| 90841-46-6 COA| 90841-46-6 structure
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