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CAS No. : | 2476-35-9 | MDL No. : | MFCD00093713 |
Formula : | C8H7BrO3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | JFDUXZIRWBYBAQ-UHFFFAOYSA-N |
M.W : | 231.04 | Pubchem ID : | 881739 |
Synonyms : |
|
Num. heavy atoms : | 12 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.12 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 47.59 |
TPSA : | 46.53 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.42 cm/s |
Log Po/w (iLOGP) : | 1.64 |
Log Po/w (XLOGP3) : | 1.82 |
Log Po/w (WLOGP) : | 2.16 |
Log Po/w (MLOGP) : | 2.06 |
Log Po/w (SILICOS-IT) : | 1.89 |
Consensus Log Po/w : | 1.91 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.56 |
Log S (ESOL) : | -2.66 |
Solubility : | 0.509 mg/ml ; 0.0022 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.42 |
Solubility : | 0.885 mg/ml ; 0.00383 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -2.76 |
Solubility : | 0.403 mg/ml ; 0.00175 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.5 |
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 |
---|---|---|
95% | With sulfuric acid; nitric acid; at -10 - 0℃; for 0.166667h; | To a solution of 1 (22 g, 95.2 mmol) in conc H2SO4 (150 mL) at -10 C. was added a solution of fuming nitric acid (8 mL, 190 mmol) in conc H2SO4 (40 mL) dropwisely to keep the internal temperature below 0 C. After the addition, the reaction was stirred for 10 min at 0 C. then poured into ice. The white precipitate was filtered, rinsed with water and dried to give the crude product 2 (25 g, 95%) as a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In N,N-dimethyl-formamide; at 20℃; for 3.5h; | Example 65; 7-[1-(5-bromo-2-methoxybenzoyl)piperidin-4-yl]-3,3-dimethyl-2-oxa-7-azaspiro[4.5]decan-1-one; [Show Image] To a suspension of <strong>[2476-35-9]5-bromo-2-methoxybenzoic acid</strong> (0.62 g, 2.7 mmol), 3,3-dimethyl-7-(piperidin-4-yl)-2-oxa-7-azaspiro[4.5]decan-1-one dihydrochloride (0.82 g, 2.4 mmol) obtained in Reference Example 53, 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.70 g, 3.6 mmol) and 1-hydroxybenzotriazole monohydrate (0.57 g, 3.6 mmol) in N,N-dimethylformamide (24 mL) was added triethylamine (0.73 g, 7.26 mmol), and the mixture was stirred at room temperature for 3.5 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (developing solvent; hexane:ethyl acetate=1:1?0:1) to give the title compound (1.1 g, yield 95%) as white crystals. EI(pos) 480 [M+H]+ |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With 1,1'-carbonyldiimidazole; In dichloromethane; for 72.25h; | Treat a solution of <strong>[2476-35-9]5-bromo-2-methoxybenzoic acid</strong> (40.0 g, 173 mmol) in anhydrous dichloromethane (400 mL) with neat 1,1'-carbonyldiimidazole (28.2 g, 173 mmol). Add N, O-dimethylhydroxylamine hydrochloride (16.9 g, 173 mmol) after about 15 min and stir for about 72 h. Transfer to a separatory funnel and wash with 1 N hydrochloric acid (2 x 100 mL), saturated sodium bicarbonate (2 x 100 mL), saturated aqueous sodium chloride (100 mL), dry (magnesium sulfate), filter and concentrate to give the title compound as an off-white solid (41.3 g, 87% yield). ¹H NMR (CDCl3) No. 7.44 (dd, J = 8.8, 2.4 Hz, 1H), 7.4 (br s, 1H), 6.80 (d, J = 8.8 Hz, 1H), 3.83 (s, 3H), 3.5 (br s, 3H), 3.4 (br s, 3H) ; MS (ES): m/z = 275.9 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
[206.3] 2.022 g of 5-Bromo-2-methoxybenzoic acid, 1.733 g of 3-carboxymethylboronic acid, 40 mg of palladium acetate and 2.5 g of sodium acetate were dissolved in 20 ml of water, and the mixture was stirred overnight at room temperature. The reaction mixture was extracted with ethyl acetate and the aqueous layer was acidified with hydrochloric acid, and the precipitated crystals were filtered. The crystals were washed with water and dried under reduced pressure to give 2.687 g of the title compound.1H-NMR(CDCl3) delta: 3.86 (s, 3H) 3.88 (s, 3H) 7.24 (d, J=8.8Hz, 1H) 7.60 (t, J=8.0Hz, 1H) 7.86 (dd, J=2.4, 8.8Hz, 1H) 7.90-7.94 (m, 3H) 8.13 (s, 1H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
16.03 g (57.9 mmol, 90%) | With thionyl chloride;AlCl3; In water; N,N-dimethyl-formamide; toluene; benzene; | (5-bromo-2-hydroxy-phenyl)-phenyl-methanone (18) 10.07 ml (138.8 mmol, 2.2 eqv) SOCl2 was added to a solution of 14.77 g (63.9 mmol) <strong>[2476-35-9]5-Bromo-2-methoxy-benzoic acid</strong> (17) in 140 ml dry toluene, followed by 0.5 ml (6.5 mmol, 0.1 eqv) DMF. After stirring this solution for 1.5 h at 70 C. the solvent was evaporated and the the crude acyl chloride was dissolved in 75 ml of dry benzene. This solution was then added cautiously under stirring to a suspension of 10.30 g (77.3 mmol, 1.2 eqv) AlCl3 in 80 ml dry benzene at 10 C. After complete addition the resulting mixture was refluxed for 5 h and then quenched by adding H2O and conc. hydrochloric acid. The aq. layer was extracted with EtOAc and the comb. org. fractions were dried over NaSO4 and evaporated. Column chromatography (CH2Cl2) yielded 16.03 g (57.9 mmol, 90%) 18 as a yellow solid: Rf (CH2Cl2) 0.67; 1H NMR (500 MHz, CDCl3) delta6.99 (d, 1H, J=8.99 Hz), 7.52-7.68 (m, 6H), 7.70 (d, 1H, J=2.36 Hz), 11.91 (s, 1H); LRMS (EI) m/z 278 (80), 277 (100), 276 (86), 275 (92), 201 (31), 200 (22), 199 (30) 198 (20), 105 (63), 77 (57), 63 (19); HRMS (EI) Calcd. for C13H9BrO2: 275.978591. Found: 275.977717. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1.2 g (67%) | With triethylamine; In N-methyl-acetamide; dichloromethane; N,N-dimethyl-formamide; | 3-(2-Pyridyl)-5-(5-bromo-2-methoxyphenyl)-1,2,4-oxadiazole A mixture of <strong>[2476-35-9]5-bromo-2-methoxybenzoic acid</strong> (1.49 g, 6.45 mmol) in dichloromethane (10 mL) was treated with 2M oxalyl chloride (9.7 ml, 19.4 mmol, dichloromethane) and 3 drops of N,N-dimethylformamide. The mixture was stirred 4 hours at room temperature. The solvent and excess reagent were removed in vacuo. The residue was treated with pyrid-2-ylamidoxime (884 mg, 6.45 mmol) and triethylamine (1.95 g, 19.35 mmol) in dichloromethane (10 mL). The mixture was then heated in dimethylformamide (10 mL) for 2 hours at 120 C. Standard work up, afforded 1.2 g (67%) of 3-(2-pyridyl)-5-(5-bromo-2-methoxyphenyl)-1,2,4-oxadiazole. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydroxide; dimethyl sulfate; In dichloromethane; water; | The starting material is prepared as follows: The solution of 110 g of 5-bromosalicylic acid in 900 ml of water and 48 g of sodium hydroxide is stirred while 60 ml of dimethyl sulfate are added. The mixture is stirred at 70 for 3 hours, whereupon 50 ml of 50% aqueous sodium hydroxide are added, followed slowly by 60 ml of dimethyl sulfate. After stirring at 70 for 6 hours the last step is repeated and the mixture warmed 17 hours longer. It is cooled in an ice bath, filtered, the filtrate stirred with methylene chloride and neutralized with cold 5 N aqueous hydrochloric acid. The organic phase is separated, dried and evaporated to yield the 5-bromo-2-methoxybenzoic acid melting at 115-117. The solution of 62.5 g thereof in 120 ml of thionyl chloride is refluxed for 2 hours and the residue dissolved in 300 ml of methylene chloride. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0℃; for 15h; | Example 9; tert-Butyldimethylsilyl-5-deutero-2-methoxybenzoate; A solution of 58 mmol of <strong>[2476-35-9]5-bromo-2-methoxybenzoic acid</strong> (Auerback J et. al. US Patent 5,248,817 to Merck) and 60 mmol of diisopropylethylamine in 100 mL of methylene chloride is cooled in ice/water under argon and treated with 58 mmol of tert-butyldimethylsilyl chloride. The mixture is stirred for 15 h, warming slowly to ambient temperature, then is diluted with 200 mL of ether and washed with water and brine, dried over MgSO4, and concentrated in vacuo. Silica gel flash chromatography (EtOAc/hexanes eluant) yields the title product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
To a mixture of 3,3-dimethylbutyraldehyde (Aldrich) (5 mL, 39.8 mmol) and Example 278A (641.0 mg, 4.0 mmol) was added a mixture of dimethylsulfoxide (560 muL, 8 mmol) and 12 N aqueous HCl (667 muL, 8 mmol). The reaction mixture was heated at 40 0C overnight. The mixture was concentrated and the residue was dried under vacuum for 2 hours. The residue (252 mg. 0.9 mmol) was dissolved in tetrahydrofuran (10 mL). To this solution was added <strong>[2476-35-9]5-bromo-2-methoxy-benzoic acid</strong> (209.0 mg, 0.9 mmol), N-(3-dimethylaminopropyl)-N-ethylcarbodimide hydrochloride (73 mg, 0.9 mmol), 1 -hydroxybenzotriazole (122.0 mg, 0.9 mmol) and triethylamine (315.0 muL, 2.3 mmol). The mixture was stirred overnight at 80 0C, and cooled to room temperature. The mixture was diluted with ethyl acetate, washed with 1 M aqueous NaHCO3, dried (Na2SO4), filtered and concentrated.The residue was purified by flash chromatography using an Analogix Intelliflash280 (SiO2, 0-75 % ethyl acetate in hexanes) to afford the title compound. 1H NMR (300 MHz, dimethylsulfoxide-Jg) delta 1.32 (s, 9 H), 1.58 - 1.71 (m, 1 H), 1.75 - 1.86 (m, 2 H), 1.87 - 2.00 (m, 1 H), 3.64 (dd, J=15, 6.8 Hz, 1 H), 3.78 (s, 3 H), 3.79 - 3.83 (m, 1 H), 4.19 (d, J=5.8 Hz, 2 H), 4.23 - 4.35 (m, 1 H), 7.05 (d, J=8.8 Hz, 1 H), 7.25 (s, 1 H), 7.56 (dd, J=8.8, 2.7 Hz, 1 H), 7.76 (d, J=2.7 Hz, 1 H |
Tags: 2476-35-9 synthesis path| 2476-35-9 SDS| 2476-35-9 COA| 2476-35-9 purity| 2476-35-9 application| 2476-35-9 NMR| 2476-35-9 COA| 2476-35-9 structure
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