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CAS No. : | 89694-44-0 | MDL No. : | MFCD06659859 |
Formula : | C7H8BBrO3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | BJQKEDXKQVNQPR-UHFFFAOYSA-N |
M.W : | 230.85 | Pubchem ID : | 25266062 |
Synonyms : |
|
Num. heavy atoms : | 12 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.14 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 50.46 |
TPSA : | 49.69 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.65 cm/s |
Log Po/w (iLOGP) : | 0.0 |
Log Po/w (XLOGP3) : | 1.49 |
Log Po/w (WLOGP) : | 0.14 |
Log Po/w (MLOGP) : | 0.76 |
Log Po/w (SILICOS-IT) : | -0.06 |
Consensus Log Po/w : | 0.46 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.45 |
Solubility : | 0.823 mg/ml ; 0.00356 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.14 |
Solubility : | 1.67 mg/ml ; 0.00723 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -2.28 |
Solubility : | 1.22 mg/ml ; 0.0053 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.02 |
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: |
* 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 |
---|---|---|
61% | With N-Bromosuccinimide; triphenylphosphine sulfide In dichloromethane at 20℃; for 48 h; Inert atmosphere | Under an argon atmosphere,To a 300 mL 2-diameter eggplant-shaped flask, 3-methoxyphenylboronic acid (12)(9.12 g, 60.0 mmol),Triphenylphosphine sulfide (932 mg, 6.00 mmol),Dichloromethane (200 mL) was added,This was stirred to make a homogeneous solution.In contrast, N-bromosuccinimide (13.0 g, 72.0 mmol) was added,And the mixture was stirred at room temperature for 2 days.To the reaction mixture was added a saturated aqueous solution of sodium thiosulfate to stop the reaction, followed by extraction with dichloromethane (100 mL × 3).The combined organic layer was washed with saturated brine and dried over sodium sulfate.After filtration, concentration under reduced pressure gave a crude product.Purification by silica gel column chromatography (290 g, n-hexane / acetone = 1/1) gave 2-bromo-5-methoxyphenylboronic acid (8b) (8.45 g, 36.6 mmol, yield 61.0 percent) Was obtained. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | Example 142 Synthesis of 4-(7-(2-bromo-5-hydroxyphenyl)-5-methylbenzo[e][1,2,4]triazin-3-ylamino)-N-(2-(pyrrolidin-1-yl)ethyl) benzenesulfonamide hydrochloride The title compound was synthesised as shown by the reaction scheme (CLXV). The intermediate compounds 57 and 58 shown on scheme (CLXV) were prepared as follows. Compound 57 was prepared by using a method that was analogous to that used to synthesize compound 30 shown on scheme (CXLI) and described in Example 128, except <strong>[89694-44-0]2-bromo-5-methoxyphenylboronic acid</strong> (compound 56) (233 mg, 1.1 mmol) and 7-bromo-5-methylbenzo[e][1,2,4]triazin-3-amine (compound 32) (240 mg, 1.0 mmol) were used to afford compound 57 (300 mg, 87%) as a yellow solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; ethanol; water; for 16h;Heating / reflux; | Compound 235: 3-2(-bromo-5-methoxyphenyl)-2-fluoro-5-methyl-rhoyridne; To a mixture of 2-fluoro-3-iodo-5-methylpyridine (4.65 g, 19.6 mmol) and Pd(PPh3)4 (2.26 g, 1.96 mmol) in DME (200 mL) were added a solution of 2-bromo-5- methoxyphenylboronic acid (4.99 g, 21.6 mmol) in EtOH (15 mL). To the above mixture was added an aqueous solution of Na2CO3 (3 M, 39.2 mL) and the mixture was heated under reflux for 16 h. The solution was filtered through a celite bed, concentrated and the remaining aqueous layer was extracted with ether, washed successively with water, 5% aqueous NaOH, 10% aqueous HCl, saturated aqueous NaHCO3 and brine. Organic layer was dried (Na2SO4) and concentrated and purified by flash chromatography to yield the title compound (5.3 g, 91%). |
91% | With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; ethanol; water; for 16h;Reflux; | To a mixture of 2- fluoro-3-iodo-5-methylpyridine (4.65 g, 19.6 mmol) and Pd(PPh3)4 (2.26 g, 1.96 mmol) in DME (200 mL) were added a solution of <strong>[89694-44-0]2-bromo-5-methoxyphenylboronic acid</strong> (4.99 g, 21.6 mmol) in EtOH (15 mL). To the above mixture was added an aqueous solution of Na2CO3 (3 M, 39.2 mL) and the mixture was heated under reflux for 16 h. The solution was filtered through a celite bed, concentrated and the remaining aqueous layer was extracted with ether, washed successively with water, 5% aqueous NaOH, 10% aqueous HCl, saturated aqueous NaHCO3 and brine. Organic layer was dried (Na2SO4) and concentrated and purified by flash chromatography to yield the title compound (5.3 g, 91%). 1H NMR (400 MHz, DMSO-^6) delta ppm 2.34 (s, 3 H) 3.78 (s, 3 H) 6.99 (dd, J=8.72, 3.16 Hz, 1 H) 7.02 - 7.04 (m, 1 H) 7.64 (d, J=8.84 Hz, 1 H) 7.76 (dd, J=9.47, 1.89 Hz, 1 H) 8.11 (s, 1 H). [M + H] calc'd for Ci3H12BrFNO, 296.0; found 296.2. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61% | With N-Bromosuccinimide; triphenylphosphine sulfide; In dichloromethane; at 20℃; for 48h;Inert atmosphere; | Under an argon atmosphere,To a 300 mL 2-diameter eggplant-shaped flask, 3-methoxyphenylboronic acid (12)(9.12 g, 60.0 mmol),Triphenylphosphine sulfide (932 mg, 6.00 mmol),Dichloromethane (200 mL) was added,This was stirred to make a homogeneous solution.In contrast, N-bromosuccinimide (13.0 g, 72.0 mmol) was added,And the mixture was stirred at room temperature for 2 days.To the reaction mixture was added a saturated aqueous solution of sodium thiosulfate to stop the reaction, followed by extraction with dichloromethane (100 mL × 3).The combined organic layer was washed with saturated brine and dried over sodium sulfate.After filtration, concentration under reduced pressure gave a crude product.Purification by silica gel column chromatography (290 g, n-hexane / acetone = 1/1) gave 2-bromo-5-methoxyphenylboronic acid (8b) (8.45 g, 36.6 mmol, yield 61.0 %) Was obtained. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In ethanol; water; toluene; for 4h;Reflux; | General procedure: A mixture of indazole 2 in a 1:1:1 toluene/ethanol/H2O mixture (0.043 mmol/mL), Pd(PPh3)4 (10 mol%), Na2CO3 (2.5 equiv) and boronic acid 3 (1.5-2 equiv) was refluxed for 2-4 h. Water was added and the mixture was extracted with EtOAc. The combined organic fractions were dried over MgSO4 and evaporated. Column chromatography (cyclohexane/EtOAc) provided the corresponding coupling product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
57% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,4-dioxane; water; at 95℃; for 48h;Inert atmosphere; | lb (200 mg, 0.6 mmol) was combined with <strong>[89694-44-0](2-bromo-5-methoxyphenyl)boronic acid</strong> (206 mg, 0.9 mmol), Tetrakis(triphenylphosphine)palladium (69 mg, 0.06 mmol), and potassium carbonate (165 mg, 1.2 mmol). Upon purging with argon gas the mixture was dissolved in a 4: 1 mixture of degassed dioxane/DI water (0.25M) and kept under inert argon atmosphere. The reaction mixture was then heated at 95 C for 48 h. Dioxane was then evaporated in vacuo and the reaction mixture was dissolved in 4:6 DI watenethyl acetate and the organic layer was collected and concentrated. The organic extract was then purified by FCC (gradient of hexanes: ethyl acetate 95:5 to 80:20) to yield 139 mg of an orange oil in 57 % Yield. NMR (400 MHz, CDCh) delta 8.62 (s, 1H), 7.51 (d, J= 8.8 Hz, 1H), 7.31 (s, 1H), 6.94 (d, J= 3.1 Hz, 1H), 6.79 (dd, J = 8.8, 3.1 Hz, 1H), 5.31 - 5.21 (m, 1H), 3.78 (s, 3H), 2.32 - 2.21 (m, 2H), 1.96 - 1.86 (m, 4H), 1.84 - 1.73 (m, 2H). 13C NMR (126 MHz, CDCh) delta 158.30, 152.03, 150.89, 150.40, 134.88, 132.93, 125.97, 118.53, 116.17, 115.68, 115.29, 114.92, 55.93, 55.53, 32.92, 24.16. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,4-dioxane; water; at 95℃; for 48h;Inert atmosphere; | 2b (179 mg, 0.52 mmol) was combined with <strong>[89694-44-0](2-bromo-5-methoxyphenyl)boronic acid</strong> (178 mg, 0.77 mmol), Tetrakis(triphenylphosphine)palladium (60 mg, 0.052 mmol), and potassium carbonate (142 mg, 1.05 mmol). Upon purging with argon gas the mixture was dissolved in a 4: 1 mixture of degassed dioxane:DI water (0.25M) and kept under inert argon atmosphere. The reaction mixture was then heated at 95 C for 48 h. Dioxane was then evaporated in vacuo and the reaction mixture was dissolved in 4:6 DI watenethyl acetate and the organic layer was collected and concentrated. The organic extract was then purified by FCC (gradient of hexanes: ethyl acetate 95:5 to 80:20) to give 124 mg of a yellow oil in 61 % Yield, NMR (400 MHz, CDCb) delta 8.62 (s, 1H), 7.51 (d, J= 8.8 Hz, 1H), 7.36 (s, 1H), 6.94 (d, J= 3.1 Hz, 1H), 6.80 (dd, J= 8.8, 3.1 Hz, 1H), 3.79 (s, 3H), 1.82 (s, 9H).13C NMR (101 MHz, CDCb) delta 158.28, 152.07, 150.88, 149.39, 135.22, 132.85, 126.41, 118.49, 116.72, 116.37, 115.22, 113.58, 58.00, 55.51, 29.26. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With sodium hydrogencarbonate; copper(II) sulfate; In methanol; at 20℃; for 48h;Inert atmosphere; | General procedure: To a mixture of NaHCO3 (1.01 g, 12.0 mmol, 2.0 equiv) and CuSO4 (95.8 mg, 0.600 mmol, 10 mol %) wasadded a solution of S-methyl 4-toluenethiosulfonate (2) (1.21 g, 6.00 mmol) and 2-bromophenylboronic acid (1a)(1.81 g, 9.00 mmol, 1.5 equiv) dissolved in MeOH (40 mL) at room temperature. After stirring for 48 h at thesame temperature, to the mixture was added an aqueous saturated ammonium chloride solution (10 mL). Themixture was extracted with EtOAc (50 mL 3), and the combined organic extract was washed with brine (20 mL),dried (Na2SO4), and after filtration, the filtrate was concentrated under reduced pressure. The residue was purifiedby flash column chromatography (silica-gel 30 g, n-hexane) to give 2-bromophenyl methyl sulfide (867 mg, 4.27mmol, 71.1%) as a colorless oil. |
72.4% | With sodium hydrogencarbonate; copper(II) sulfate; In methanol; at 20℃; for 96h;Inert atmosphere; | Under an argon atmosphere, copper (II) sulfate anhydride (79.8 mg, 0.500 mmol) and sodium hydrogencarbonate (840 mg, 10.0 mmol) were added to a 100 mL two-necked eggplant-shaped flask.In contrast, methanol (30 mL)Was added a solution of p-tolylmethylthiosulfonate (28) (1.01 g, 5.00 mmol) and <strong>[89694-44-0]2-bromo-5-methoxyphenylboronic acid</strong> (8b) (1.73 g, 7.50 mmol), and the mixture was stirred at room temperature for 4 days did.Water was added to the reaction mixture to stop the reaction, followed by extraction with ethyl acetate (50 mL × 3).The combined organic layer was washed with saturated brine and dried over sodium sulfate.After filtration, concentration under reduced pressure gave a crude product.This was purified by silica gel column chromatography (30 g, n-hexane / dichloromethane = 5/1) to give (2-bromo-5-methoxyphenyl) methylsulfide (10b) (835 mg, 3.62 mmol,Yield 72.4%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,4-dioxane; water; at 90℃; for 21h; | A mixture of tert-butyl 4-(6- bromo-5 -chloro-7-fluorobenzo [cjisothiazol-3-yl)piperazine- 1 -carboxylate (Intermediate D, 111 mg, 0.247 mmol), <strong>[89694-44-0]2-bromo-5-methoxybenzene boronic acid</strong> (0.114 mL, 0.494 mmol), sodium carbonate (0.041 mL, 0.988 mmol), and tetrakis(triphenylphosphine)palladium (14.3 mg, 0.012 mmol) in 1,4-dioxane (1.6 mL) and water (0.4 mL) was heated at 90 C for 21 h. The reaction mixture then concentrated in vacuo, adsorbed onto silica gel, and purified by column chromatography (silica gel, 0-20% (3:1) EtOAc/EtOH in heptane) to furnish tertbutyl 4-(6-(2-bromo-5 -methoxyphenyl)-5-chloro-7-fluorobenzo[cjisothiazol-3-yl)piperazine- 1-carboxylate: m/z (ESI, +ve) 558.1 (M+H)t | |
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,4-dioxane; water; at 90℃; for 21h; | A mixture of tert-butyl 4-(6-bromo-5-chloro-7-fluorobenzo[c]isothiazol-3-yl)piperazine-1-carboxylate (Intermediate D, 111 mg, 0.247 mmol), <strong>[89694-44-0]2-bromo-5-methoxybenzene boronic acid</strong> (0.114 mL, 0.494 mmol), sodium carbonate (0.041 mL, 0.988 mmol), and tetrakis(triphenylphosphine)palladium (14.3 mg, 0.012 mmol) in 1,4-dioxane (1.6 mL) and water (0.4 mL) was heated at 90 C. for 21 h. The reaction mixture then concentrated in vacuo, adsorbed onto silica gel, and purified by column chromatography (silica gel, 0-20% (3:1) EtOAc/EtOH in heptane) to furnish tert-butyl 4-(6-(2-bromo-5-methoxyphenyl)-5-chloro-7-fluorobenzo[c]isothiazol-3-yl)piperazine-1-carboxylate: m/z (ESI, +ve) 558.1 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene at 30℃; for 45h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / toluene; ethanol; water / 45 h / 30 °C / Inert atmosphere 2: potassium <i>tert</i>-butylate / dimethyl sulfoxide / 16 h / 150 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,2-dimethoxyethane; water for 6h; Reflux; Inert atmosphere; |
Tags: 89694-44-0 synthesis path| 89694-44-0 SDS| 89694-44-0 COA| 89694-44-0 purity| 89694-44-0 application| 89694-44-0 NMR| 89694-44-0 COA| 89694-44-0 structure
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P410 + P412 | Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF. |
P411 + P235 | Keep cool. |
Disposal | |
Code | Phrase |
P501 | Dispose of contents/container to ... |
P502 | Refer to manufacturer/supplier for information on recovery/recycling |
Physical hazards | |
Code | Phrase |
H200 | Unstable explosive |
H201 | Explosive; mass explosion hazard |
H202 | Explosive; severe projection hazard |
H203 | Explosive; fire, blast or projection hazard |
H204 | Fire or projection hazard |
H205 | May mass explode in fire |
H220 | Extremely flammable gas |
H221 | Flammable gas |
H222 | Extremely flammable aerosol |
H223 | Flammable aerosol |
H224 | Extremely flammable liquid and vapour |
H225 | Highly flammable liquid and vapour |
H226 | Flammable liquid and vapour |
H227 | Combustible liquid |
H228 | Flammable solid |
H229 | Pressurized container: may burst if heated |
H230 | May react explosively even in the absence of air |
H231 | May react explosively even in the absence of air at elevated pressure and/or temperature |
H240 | Heating may cause an explosion |
H241 | Heating may cause a fire or explosion |
H242 | Heating may cause a fire |
H250 | Catches fire spontaneously if exposed to air |
H251 | Self-heating; may catch fire |
H252 | Self-heating in large quantities; may catch fire |
H260 | In contact with water releases flammable gases which may ignite spontaneously |
H261 | In contact with water releases flammable gas |
H270 | May cause or intensify fire; oxidizer |
H271 | May cause fire or explosion; strong oxidizer |
H272 | May intensify fire; oxidizer |
H280 | Contains gas under pressure; may explode if heated |
H281 | Contains refrigerated gas; may cause cryogenic burns or injury |
H290 | May be corrosive to metals |
Health hazards | |
Code | Phrase |
H300 | Fatal if swallowed |
H301 | Toxic if swallowed |
H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
H304 | May be fatal if swallowed and enters airways |
H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
Sorry,this product has been discontinued.
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