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CAS No. : | 16426-64-5 | MDL No. : | MFCD00234252 |
Formula : | C7H4BrNO4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | CEXGTXNIIFSPSF-UHFFFAOYSA-N |
M.W : | 246.02 | Pubchem ID : | 313534 |
Synonyms : |
|
Num. heavy atoms : | 13 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 49.92 |
TPSA : | 83.12 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) : | -6.38 cm/s |
Log Po/w (iLOGP) : | 0.89 |
Log Po/w (XLOGP3) : | 2.0 |
Log Po/w (WLOGP) : | 2.06 |
Log Po/w (MLOGP) : | 1.27 |
Log Po/w (SILICOS-IT) : | -0.22 |
Consensus Log Po/w : | 1.2 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.56 |
Log S (ESOL) : | -2.83 |
Solubility : | 0.36 mg/ml ; 0.00146 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.37 |
Solubility : | 0.104 mg/ml ; 0.000425 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -2.01 |
Solubility : | 2.4 mg/ml ; 0.00977 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 2.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.83 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H332-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 |
---|---|---|
68.1% | With potassium permanganate In pyridine; water for 5 h; Reflux | To a mixture of 2-bromo-4-nitrotoluene (25g, 116mmol), pyridine (100mL) and water (200mL) was added KMnO4 (102g, 642mmol) in portions. After the mixture was refluxed for 5h, an additional amount of KMnO4 (27.5g, 174mmol) was added. The mixture was refluxed and stirred for overnight, then filtered over celite. The filtrate was acidified with concentrated HCl (110mL), extracted with EtOAc (600mL), dried over anhydrous Na2SO4, and evaporated under vacuum to give compound 19 as a solid (19.4g, 68.1percent yield). 1H NMR (400MHz, CD3OD): δ 8.43 (d, J=2.1Hz, 1H), 8.18 (dd, J=8.5, 2.1Hz, 1H) and 7.86 (d, J=8.5Hz, 1H) ppm; mp: 153–155°C. |
66% | With pyridine; potassium permanganate In water at 70℃; for 8 h; Heating / reflux | (a) Synthesis of 2-bromo-4-nitrobenzoic acid Water (40 ml) was added to a solution of 2-bromo-4-nitrotoluene (4.41 g, 20.0 mmol) in pyridine (20 ml), and the resulting mixture was heated at 70°C. Potassium permanganate (19.0 g, 120 mmol) was added thereto over a period of 40 minutes and the resulting mixture was refluxed for 8 hours. After completion of the reaction, the suspension thus obtained was filtered. The filtrate was acidified with 6N-hydrochloric acid under ice-cooling. The resulting suspension was filtered to obtain 2-bromo-4-nitrobenzoic acid (1.63 g). Hydrochloric acid was added to the filtrate, followed by extraction with ethyl acetate and chloroform. The organic layer was dried over magnesium sulfate and filtered. The filtrate was concentrated to obtain 2-bromo-4-nitrobenzoic acid (1.61 g, total amount 3.24 g, 66percent). |
28% | With sodium dichromate; sulfuric acid In acetic acid at 75 - 110℃; for 3 h; | Compound 21 used in the preparation of compound 24 was prepared as follows. Sodium dichromate dihydrate (151 gm) was added to glacial acetic acid (575 ml) followed by 2-bromo-4-nitro-toluene (49.7 gm). To this solution was added dropwise sulphuric acid (175 ml) at such a rate to maintain the temperature between 75-85° C. This mixture was heated to 100-110° C. for 3 h cooled to 50° C. and poured onto ice (1 litre). The aqueous phase was extracted with ethyl acetate, the organic layer back extracted with Aqueous sodium hydroxide solution and the resulting basic aqueous layer acidified with concentrated hydrochloric acid. The precipitated solid was filtered, washed with water and air dried to give 15.72 gm (28percent) of 2-bromo-4-nitro-benzoic acid (compound 26) as a white solid. NMR H1NMR (CDCl3) δ: 7.42 (1H, d), 8.08 (1H, q), 8.42 (1H, d) |
51% | With hydrogenchloride In diethyl ether; sulfuric acid; water | 2-bromo-4-nitrobenzoic Acid To a solution of 2-bromo-4-nitrotoluene (7.0 g, 32 mmol) that was dissolved in if sulfuric acid (98percent, 50 mL) and placed in a water bath to maintain ambient temperature was added dropwise a solution of chromium trioxide (7.5 g, 75 mmol) in water (8 mL). Following addition, the mixture was poured onto 200 mL of ice, the precipitate was collected and washed with water (1*100 mL). The crude product was taken up in diethyl ether (50 mL), extracted with aqueous NaHCO3solution (2*25 mL). The combined bicarbonate layers were acidified by the addition of 12M HCl, extracted with diethyl ether (2*25 mL). The second set of diethyl ether layers was washed with brine (1*25 mL), dried (MgSO4), filtered, and concentrated under reduced pressure to provide the titled compound 4.0 g (51percent). 1H NMR (300 MHz, d6-DMSO) δ8.48 (d, 1H, J=2.4), 8.28 (dd, 1H, J=2.0, 8.5), 7.95 (d, 1H, J=8.5); MS (ESI) m/z=244, 246 (M-H). |
72 g | With pyridine; potassium permanganate In water at 80℃; | Intermediate 10A. 2-Bromo-4-nitro-benzoic acid: To a warm (80 °C) solution of pyridine (500 mL) and water (1 L) was added 4-nitro-2-bromo toluene (100 g, 0.46 mol). The resulting suspension was stirred until it became a clear solution. To the above reaction mixture was then added KMn04 (600 g, 3.8 mol) in portions over 1.5 h and stirring was continued overnight. The reaction mixture was then cooled to rt and then 10percent aqueous NaOH (200 mL) was added. After 15 min, the reaction was filtered to remove the solids. The solids were then rinsed with 10percent aqueous NaOH (5x100 mL). The filtrate was extracted with MTBE (3x250 mL). The clear aqueous layer was cooled to 10 °C and then it was acidified with concentrated HC1. The aqueous layer was again extracted with MTBE (4x500 mL). The organic layers were combined, dried over Na2S04, filtered and concentrated to afford 72 g of Intermediate 10A. 1H NMR (400 MHz, DMSO-d6) δ 7.96 (d, J = 8 Hz, 1H), 8.28 - 8.48 (m, 1H), 8.49 (d, J = 2.4 Hz, 1H), 14.1 (br. s, 1H) ppm. |
72 g | With potassium permanganate In pyridine; water | [00355] Intermediate 18 A. 2-Bromo-4-nitro-benzoic acid: To a warm (80 °C) solution of pyridine (500 mL) and water (1 L) was added 4-nitro-2-bromo toluene (100 g, 0.46 mol). The resulting suspension was stirred until it became a clear solution. To the above reaction mixture was then added KMn04 (600 g, 3.8 mol) in portions over 1.5 h and stirring was continued overnight. The reaction mixture was then cooled to rt and then 10percent aqueous NaOH (200 mL) was added. After 15 min, the reaction was filtered and the solid was rinsed with 10percent> aqueous NaOH (5x100 mL). The filtrate was extracted with MTBE (3x250 mL). The clear aqueous layer was cooled to 10 °C and then it was acidified with concentrated HC1. The aqueous layer was again extracted with MTBE (4x500 mL). The combined organic layers were dried over sodium sulfate, filtered, and concentrated to afford 72 g of Intermediate 18A. 1H NMR (400 MHz, DMSO-d6) δ 7.96 (d, J= 8 Hz, 1H), 8.28 - 8.48 (m, 1H), 8.49 (d, J= 2.4 Hz, 1H), 14.1 (br. s, lH) ppm. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 0 - 25℃; for 12 h; | Example 3: l-(4-((lH-indol-3-yl)methyl)-3-ethylphenyl)-3-(2-(4-methylpiperazin- 1- yPethyPurea [00101] Step 1. To a solution 2-bromo-4-nitrobenzoic acid (100.0 g, 0.4 mol) and 1,8- diazabicyclo[5.4.0]undec-7-ene (80 g, 0.6 mmol) in acetonitrile (500 mL) was added Mel (120 g, 0.8 mol) dropwise at 0 °C. The resulting mixture was stirred at 25 °C for 12 h. The mixture was concentrated and diluted with 300 mL CH2C12, washed with 2 N HC1 (3x100 mL), 2 N NaOH (2x100 mL), and brine, dried over anhydrous Na2S04, and concentrated to give methyl 2- bromo-nitrobenzoate (104 g, 100percent) as a white solid. 1H NMR (400 MHz, CDC13) δ: 4.01 (s, 3H), 7.93-7.95 (d, J = 8.8 Hz, 1H), 8.22-8.24 (m, 1H), 8.53-8.54 (m, 1H). |
92% | With potassium carbonate In N,N-dimethyl-formamide | Example 54B methyl 2-bromo-4-nitrobenzoate To a solution containing 2-bromo-4-nitrobenzoic acid (1.0 g, 4.06 mmol) and K2CO3 (560 mg) in N,N-dimethylformamide (5 mL) was added methyl iodide (500 μL, 8.03 mmol). The mixture was stirred at ambient temperature for 1 hour, poured into water (30 mL) and extracted with diethyl ether (3*10 mL). The combined ether layers were washed with water (1*10 mL), brine (1*10 mL), dried (MgSO4), filtered, and concentrated under reduced pressure to provide the titled compound (970 mg, 92percent). 1H NMR (300 MHz, CDCl3) δ8.52 (d, 1H, J=2.4), 8.21 (dd, 1, J=2.0, 8.5), 7.92 (d, 1, J=8.8), 3.99 (s,3); MS (ESI) m/z=259 (M-H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | With thionyl chloride In methanol; dichloromethane | Step a) 2-Bromo-4-nitrobenzoic acid methyl ester Thionyl chloride (3.99 ml, 54.6 mmol) was added via syringe at room temperature to a methanol solution (500 ml) of 2-bromo-4-nitrobenzoic acid (Chem. Ber. 1961, 835) (17.9 g, 72.9 mmol). The reaction was stirred at room temperature for 16 hours. The volatiles were removed in vacuo, the residue dissolved in dichloromethane, washed with 1N sodium hydroxide, and the organic layer separated and dried (MgSO4). Evaporation gave a light yellow solid (10.9 g, 83percent) m.p. 73°-74° C., which was used without further purification in Example 361, step b. Analysis for: C8 H6 Br N O4 Calcd: C, 34.17; H, 1.64; N, 5.69. Found: C, 33.92; H, 1.49; N, 5.67. |
83% | With thionyl chloride In methanol; dichloromethane | Step a) 2-Bromo-4-nitrobenzoic acid methyl ester Thionyl chloride (3.99 ml, 54.6 mmol) was added via syringe at room temperature to a methanol solution (500 ml) of 2-bromo-4-nitrobenzoic acid (Chem. Ber. 1961, 835) (17.9 g, 72.9 mmol). The reaction was stirred at room temperature for 16 hours. The volatiles were removed in vacuo, the residue dissolved in dichloromethane, washed with 1N sodium hydroxide, and the organic layer separated and dried (MgSO4). Evaporation gave a light yellow solid (10.9 g, 83percent) m.p. 73°-74° C., which was used without further purification in Example 361, step b. Analysis for: C8 H6 Br N O4 Calcd: C, 34.17; H, 1.64; N, 5.69. Found: C, 33.92; H, 1.49; N, 5.67. |
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