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CAS No. : | 62621-09-4 | MDL No. : | MFCD03618407 |
Formula : | C9H9NO4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | JJHCLPDHYBSSHC-UHFFFAOYSA-N |
M.W : | 195.17 | Pubchem ID : | 15088700 |
Synonyms : |
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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 |
---|---|---|
100% | With ammonium formate;palladium 10% on activated carbon; In ethanol; at 40℃; for 2h; | Intermediate 7; Methyl 4-amino-2-methylbenzoate; To a solution of <strong>[62621-09-4]methyl 2-methyl-4-nitrobenzoate</strong> (Intermediate 5) (3.25 g, 16.6 mmol) in ethanol was added Pd/C 10% (catalytic quantity) and ammonium formate (10.5 g, 0.17 mmol). The mixture was stirred at 400C for 2 hours. The mixture was filtered on celite, washed with diethyl ether. The filtrate was evaporated and the residue was diluted with diethyl ether, washed with water. The organic phase was dried over Na2SC>4, filtered and evaporated to give the title compound as brown oil (2.8 g, quantitative yield). NMR1H NMR (300 MHz), CDCI3 delta: 7.74 (d, 1 H, J=9.20 Hz), 6.41 (m, 2H), 3.75 (s, 3H), 2.47 (s, 3H). |
With iron(III) chloride; water; hydrazine; In ethanol; for 3h;Heating / reflux; Charcoal; | Example 1: Synthesis of PDZ domain inhibitor (2-(l-HydroxypentvD-3-(2-phenvlethvl)-6-methvl)indole-5-carboxylic acid [Formula (I); Table 1A, compound 11; [0067] The general scheme for this synthesis was (Scheme D):; [0068] Methyl (4-amino-5-iodo-2-methyl)benzoate (4); A mixture of 2-iodo-5-nitrotoluene (1,10 g), triethylamine (16 mL), palladium acetate (68 mg), methanol (20 mL) and DMF (10 mL) was stirred at 90C overnight under carbon monoxide atmosphere (1 atm). The reaction mixture was diluted with ethyl acetate (200 mL), washed with water twice (100 mL each) followed by brine (100 mL), dried (Na2S04), and evaporated. The residue was filtered through a short pad of silica gel and evaporated to give 2 as a crude oil. A mixture of 2, ethanol (140 mL), water (2 mL), hydrazine monohydrate (3.8 mL), ferric trichloride (0.17 g) and charcoal (0.1 g) was stirred under reflux for 3 hours. The reaction mixture was filtrated, diluted with ethyl acetate (200 mL), washed with water twice (100 mL each) followed by brine (100 mL), dried (Na2S04), and evaporated. The residue was filtered through a short pad of silica gel and evaporated to give 3 as a crude oil. To a mixture of 3, methanol (33 mL), calcium carbonate (10 g), iodine monochloride solution (33 mL, 1M in dichloromethane) was added slowly at 4C and stirred overnight at the ambient temperature. The reaction mixture was filtrated, diluted with ethyl acetate (200 mL), washed with aqueous sodium sulfite solution (100 mL), followed by brine (100 mL), dried (Na2SC>4), and evaporated. The residue was purified by column chromatography (silica gel 0.2 L, eluent: 10% ethyl acetate in hexanes) and evaporated to give 4 (4.30 g) as pale brown crystals. *H NMR (CDC13, 400 MHz) 8 8.28 (s, 1H), 6.54 (s, 1H), 4,39 (broad s, 2H), 3.84 (s, 3H), 2.50 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With N-Bromosuccinimide; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; In tetrachloromethane; at 85℃; for 12h; | To a solution of methyl 2-methyl-4-nitro-benzoate (3.00 g, 15.4 mmol) in CCl4 (60.0 mL) was added NBS (3.28 g, 18.4 mmol) and BOP (68.0 mg, 154 umol). The reaction mixture was stirred at 85 C. for 12 hrs. On completion, the mixture was washed with saturated NaHCO3 (20.0 mL) and brine (50.0 mL), dried over anhydrous MgSO4, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography (PE:AcOEt=3:1) to give the title compound (4.21 g, 100% yield) as a colorless oil. 1H NMR (400 MHz, CDCl3) delta 8.30 (d, J=2.0 Hz, 1H), 8.20 (dd, J=2.0, 6.4 Hz, 1H), 8.10 (d, J=6.4 Hz, 1H), 4.96 (s, 2H), 4.00 (s, 3H). |
96% | With N-Bromosuccinimide; In tetrachloromethane; for 2h;Reflux; | U) 2-Bromomethyl-4-nitro-benzoic acid methyl esterN-Bromosuccinimide (2.18 g, 12.30 mmol) was added to a stirred solution of 2- methyl-4-nitro-benzoic acid methyl ester (2 g, 10.25 mmol) and ABCN (626 mg, 2.56 mmol) in carbon tetra-chloride (80 ml) at room temperature. The reaction was heated at reflux for 2 hrs and then allowed to cool to room temperature and stirred for 15 hrs. The solvent was evaporated in vacuo and the resulting residue filtered through a pad of silica (eluting with dichloromethane). The solvent was evaporated in vacuo to afford the title compound as a yellow solid (2.70 g, 96%). HPLC retention time 4.49min. Mass spectrum (ES+) m/z 256 (M+H). |
88.8% | With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); In tetrachloromethane; at 70℃;Reflux; Irradiation; | EXAMPLE 76 2-Bromomethyl-4-nitro-benzoic acid methyl ester (2) In accordance with general method T, 4.70 g (24.00 mmol) of (1) are dissolved in 30 ml of carbon tetrachloride, with heating, and 5.00 g (28.00 mmol) of N-bromosuccinimide and 2 spatula tips of azobisisobutyronitrile are then added. The mixture is refluxed for 6 h with irradiation with a 500 W spotlight. On cooling to room temperature, succinimide separates out, and is filtered off. The filtrate is evaporated on a rotary evaporator in order to obtain the product as a yellow oil. Yield: 5.85 g (88.8%) C9H8BrNO4 (Mr=274.07); GC (method 3) 7.98 min 1H-NMR (CDCl3) in ppm: 4.96 (s, 2H, -CH2-Br), 2.71 (s, 3H, -CH3) MS m/z (%): 274 (100), 193 (38), 178 (46), 147 (12), 132 (18), 88 (9). General Method TThe substance to be halogenated is dissolved in carbon tetrachloride in a 250 ml three-necked flask with a reflux condenser and drying tube at approx. 70 C. and the stated amounts of N-bromosuccinimide and azobisisobutyronitrile are added. The mixture is refluxed for 5 h, if necessary with irradiation with a 500 W spotlight. At the end of the reaction, the N-bromosuccinimide has dissolved and has been converted into succinimide, which settles on the surface. After cooling to room temperature, the mixture is filtered with suction. The filtrate is evaporated on a rotary evaporator in order to obtain the product as a yellow - orange oil. |
78.7% | With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); In tetrachloromethane; for 20h;Reflux; | In a 500 mL, 3-neck round-bottomed flask, the intermediate (1) (20 g, 88.01 mmol) was charged with CC14 (100 mL). N-bromosuccinimide (39.16g, 220.03 mmol) and AIBN (2.16 g, 13.20 mmol) were added and the resulting mixture was refluxed for 20 h. The reaction mixture was quenched with water (500 mL), extracted with dichloromethane (200 mL X 3), and the combined organic layer was washed with saturated brine solution followed by drying over anhydrous sodium sulphate. The organic layer was evaporated under reduced pressure and the crude product obtained was purified by silica gel column chromatography to obtain pure methyl 2-(bromomethyl)-4-nitrobenzoate (2), 19 g; Yield: 78.7%; Eta NMR (400 MHz, OMSO-de) : delta 8.52 (s, 1H), 8.27-8.3(dd, 1H), 8.07-8. l(d, 1H), 5.1 (s, 2H), 3.94 (s, 1H). |
65% | With N-Bromosuccinimide; 1,1'-azobis(1-cyanocyclohexanenitrile); In tetrachloromethane; for 5h;Reflux; | To a solution of 2-methyl-4-nitrobenzoic acid methyl ester (2.0 g, 10.36 mmol) in carbon tetrachloride (80 mL) and l , azobis(cyclohexanecarbonitrile) (0.63 g, 2.56 mmol) was added N-bromosuccinimide (2.18 g, 12.25 mmol) and the resulting solution was heated at reflux for 5h and allowed to sit at room temperature overnight. The reaction was concentrated under reduced pressure and to the resulting residue was added DCM. The solid was filtered off and washed several times with DCM. The combined filtrate and washes were loaded onto a silica column and eluted with 10% EtOAc/hexane to provide slightly impure methyl 2-(bromomethyl)-4-nitrobenzoate (1.82 g, 65% yield) which was carried on as is to the next step. |
53% | With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); In tetrachloromethane; at 80℃; for 15h; | Compound methyl 2-methyl-4-nitrobenzoate 52a (5 g, 25.6 mmol) was dissolved in carbon tetrachloride (150 mL),Then N-bromosuccinimide (5.02 g, 28.2 mmol) and azobisisobutyronitrile (419 mg, 2.56 mmol) were added, heated to 80 C and stirred for 15 hours.After completion of the reaction, the solvent was removed under reduced pressure, and the residue was purified by silica gel column chromatography (petroleum ether / ethyl acetate = 100/1 to 5/1).The target product methyl 2- (bromomethyl) -4-nitrobenzoate 52b (3.7 g, white solid) was obtained, yield: 53%. |
49% | With N-Bromosuccinimide; dibenzoyl peroxide; In tetrachloromethane; at 85℃; for 21h; | A solution of Intermediate 58 (9.57 g, 49 mmol), NBS (9.6g, 54 mmol), benzoyl peroxide (121 mg,0.5 mmol) in carbon tetrachloride was heated at 85C for 18 h. The reaction was concentrated under vaccum, analysed by TLC and 1H NMR and found to have some remaining starting material. <n="103"/>The residues were added to CCl4 (40 ml) with NBS (4.4 g) and benzoyl peroxide (60 mg) then stirred at 85C for 3h. The reaction was concentrated, taken up in DCM then washed with aqueous NaHCO3 and brine. The organic phase was dried over Na2SO4 and concentrated under vacuum. The residues were purified by flash chromatography using a Biotage SP4. The desired product was isolated as an orange solid (6.58 g, 49%). 1H NMR (400 MHz, DMSO-^6) delta ppm 3.93 (s, 3 H), 5.10 (s, 2 H), 8.08 (d, 7=8.24 Hz, 1 H), 8.25 - 8.30 (m, 1 H), 8.51 (d, /=2.29 Hz, 1 H). |
48.2% | With N-Bromosuccinimide; dibenzoyl peroxide; In 1,2-dichloro-ethane; for 48h;Reflux; | A solution of 19 (2.57 g, 13.19 mmol) in 1,2-dichloroethane (100 mL) was treated with N-bromosuccinimide (2.3 g, 13.19 mmol) and benzoyl peroxide (0.26 g), and the mixture was kept at reflux for 2 days, then cooled, washed with water, and evaporated to a yellow oil (3.52 g). The oil was dissolved in acetone and silica gel (4.0 g) was added. A dry silica gel plug was obtained after evaporation of the solvent. The plug was loaded on to a silica gel column and eluted with 10% ethyl acetate in hexane to afford 20 (1.73 g, 48.2%) as a yellow oil; Rf 0.53 (hexane/EtOAc 3:1); 1H NMR (CDCl3) delta 3.89 (s, 3H, COOCH3), 4.86 (s, 2H, CH2Br), 7.98-8.23 (m, 3H, C6H3). |
44% | With N-Bromosuccinimide; dibenzoyl peroxide; In tetrachloromethane; for 7h;Inert atmosphere; Heating; | 2 - methyl-4-nitrobenzoate (. 200mg, 1 OmmoL), benzoyl peroxide (48.5mg,0.2mmoL), N_-bromosuccinimide (213mg, 1.2mmoL) was added to the CCl4 (15mL), and under protection of Ar gas, the reaction was heated at reflux for 7 hours, cooled, washed with saturated sodium bicarbonate (3 X20mL ), saturated brine (20 mL), dried and the solvent was distilled off under reduced pressure, the residue was purified by flash column chromatography, eluent PE: EpsilonAlpha = 20: 1, to give a white solid 124mg, 44% yield |
39% | With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); In tetrachloromethane; at 80℃; | Azobisisobutyronitrile (AIBN) (0.17 g, 1.02 mmol) was added to the solution of methyl 2-methyl-4-nitrobenzoate (61.2) (2.0 g, 10.2 mmol) and N-bromosuccinimide (NBS) (2.7 g, 15.2 mmol) in CCl4 (50 mL). The mixture was stirred at 80 C overnight. After cooling to room temperature, the reaction mixture was filtered and, the filtrate was concentrated to afford methyl 2-(bromomethyl)-4-nitrobenzoate (61.3) as a white solid (1.1 g, 39%). [00869] LCMS: 314.0 [M+CH3CN]+. |
With N-Bromosuccinimide;2,2'-azobis(isobutyronitrile); In tetrachloromethane; at 80℃; for 22h; | 5-Nitro-2,3-dihydroisoindol-l-one02N; [695] AIBN (58.6mg, 0.357mmol), NBS (785mg, 4.46mmol), and 2-methyl-4-nitrobenzoic acid methyl ester (696mg, 3.57mmol) were suspended in CC14 (35mL) in asealed tube. The above mixture was flushed with N2 for 5min and heated at 80C for 22h.After cooling, the solid was filtered off and the filtrate was concentrated to dryness to obtain acrude light-brown solid. To above solid was added NH3 (7 N in MeOH, 5mL), and themixture was stirred at rt for 2h and concentrated in vacua to obtain a yellow solid. This crudesolid was triturated with EtOAc (15mL) and was then cooled at -20 C. The mixture wasfiltered to obtain the title compound as yellow solid. 'H NMR (DMSO-^, 400 MHz): 5 =4.51 (s, 2 H), 7.13 (bra, 2 H), 7.91 (d, 1 H, J= 8.4 Hz), 8.25 (dd, 1 H, J= 2.0 & 8.4 Hz), 8.48(d, 1 H, J= 2.0 Hz), 9.04 (brs, 1 H). MS (ES+): m/z 179.22 (100) [MH1]. HPLC: fe = 2.14min (ZQ2000, polar_5 min). | |
With N-Bromosuccinimide;dibenzoyl peroxide; In tetrachloromethane; at 85℃; for 9h;Reflux; | Step b:[00294] A mixture of 2-methyl-4-nitro-benzoic acid methyl ester (leq.), NBS (1.1 eq.), benzoyl peroxide (0.01 eq.), and 20 mL of carbon tetrachloride is heated at 85C for 8hrs. Further NBS (0.1 eq.) is added and the whole is is refluxed 1 hrs. The mixture is washed with sat. NaHCO3 and brine, dried over MgSO4, and evaporated. The residue is purified by flash chromatography to afford the compound. | |
With N-Bromosuccinimide; dibenzoyl peroxide; In tetrachloromethane; at 85℃; | Step A: Methyl 2-(bromomethyl)-4-nitrobenzoate: Methyl 2-methyl-4-nitrobenzoate (4.2 g, 21.5 mmol) was dissolved in 100 mL CCl4 under nitrogen. N-bromosuccinimide (6.13 g, 34.4 mmol) was added, followed by benzoyl peroxide (0.104 g, 0.430 mmol). The reaction mixture was heated overnight at 85 C. Added 1 g NBS followed by 100 mg benzoyl peroxide and continued heating the reaction for 6 hours. The reaction mixture was cooled to ambient temperature, poured into 1M HCl, extracted with dichloromethane, dried over magnesium sulfate, filtered and concentrated to an oil. Purification was carried out using column chromatography (5-10% EtOAc/hexanes). | |
With N-Bromosuccinimide; dibenzoyl peroxide; In tetrachloromethane; for 4h;Reflux; Inert atmosphere; | A degassed solution of methyl 2-methyl-4-nitrobenzoate (3.5 g, 18.19 mmol), N- bromosuccinimide (3.9 g, 21.91 mmol, 1.2 eq) and benzoyl peroxide (3.63 mmoi, 0.2eq.) in 100 ml CCWwas heated at reflux for 4 hr. it was concentrated to dryness, dissolved in ether, washed 2x with water, aq. Na2S2theta3, brine, dried over MgSO4, filtered, concentrated and purified by chromatography using 15% ethyl acetate in hexanes to provide 4.11g of methyl 2-bromomethyl-4-nitrobenzoate. | |
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); In tetrachloromethane; at 79℃;Inert atmosphere; | Preparative Example 46aPreparation of 5-amino-2-cyclopropylisoindolin-1-oneStep 1: 2-cvclopropyl-5-nitroisoindoliii-1-oneAIBN (28 mg, 0.17), NBS (0.37 gram, 2.1 mmol), and the methyl 2-methyl-4-nitrobenzoate (334 g, 1.7 mmol, as prepared in Step 1, Example 44) were suspended in CCI4 (4.2 ml), the vessel evacuated and backfilled with N2 (2x) and the mixture heated under N2 at 79 C overnight. The solution was filtered, and concentrated in vacuum. The residue was dissolved in 7 N cyclopropyl amine (2.1 g, 35.9 mmol, in methanol, 18 ml), and the solution stirred for 2 hours at RT. The volatiles were removed in vacuum and the product purified by chromatography on Sitheta2 eluting with 10% acetone : DCM to give the titled compound. | |
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); In tetrachloromethane; at 80℃; for 22h;Inert atmosphere; Sealed tube; | ^nierrrsedsaie B6 S-amsnoisoindoIin-i -one Step A: methyl 2-(bromomethyl)-4-nitrobenzoate 2-methyl-4-nitrobenzoic acid methyl ester (896 mg, 3.57 mmoi), azobisisbufyronifrile (58.6 mg, 0.357 mmol) and N-bromosuccinimide (785 mg, 4.48 mmol) were suspended in carbon tetrachloride (35 mL) in a sealed tube. The above mixture was flushed with nitrogen for 5 minutes and heated at 80 C for 22 hours. After cooling, the solid was filtered off and the filtrate was concentrated to dryness to obtain the crude product methyl 2-(bromomethyl)-4-nitrobenzoate as a light-brown solid, which was used for the next step without purification. | |
With N-Bromosuccinimide; dibenzoyl peroxide; In tetrachloromethane; at 70℃; for 15h; | To solution of methyl 2-methyl-4-nitrobenzoate (350 mg, 1.8 mmol) in carbon tetrachloride (6 mL) was added NBS (500 mg, 2.8 mmol) and benzoyl peroxide (13 mg, 0.054 mmol). The reaction was then heated to 70 C for 15 hours and then cooled to ambient temperature. Once cooled, water (5 mL) was added and the aqueous layer was extracted with dichloromethane (3 X 10 mL). The combined organic layers were then dried over sodium sulfate, filtered and concentrated in vacuo. The crude residue was purified via MPLC (0- 30% EtO Ac/Hex gradient) to afford methyl 2-(bromomethyl)-4-nitrobenzoate. NMR (500 MHz, DMSO-d6): 9 (s, 1H), 8.3 (d, 1H), 8.1 (d, 1H), 7.9 (s, 1H), 4.9 (s, 2H), 4.0 (s, 3H). | |
With N-Bromosuccinimide; dibenzoyl peroxide; In tetrachloromethane; at 60℃; for 4h; | To a solutionof compound 7B (50g, 0.26 mol) in CC14 (500 mL), N-bromosuccinimide (45.8g, 0.26 mol)and benzoyl peroxide(0.12 g, 0.5 mmol) were added. The reactionmixture wasstirred 4 hr at 60C. The mixturewas cooled to RT and was washed with IN NaOHand water and it was dried overNa2S04. The solvent was evaporated to affordcrude7C (71g) as yellow oil. | |
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); In tetrachloromethane; for 22h;Reflux; | Step 2: Synthesis of 2-bromomethyl-4-nitro-benzoic acid methyl ester To a solution of 2-Methyl-4-nitro-benzoic acid methyl ester (3.08 g, 15.79 mmole) in 125 ml carbontetrachloride was added NBS (3.1 g, 17.38 mmole) and AIBN (390 mg, 2.38 mmole). The reaction mixture was heated at reflux under light for 22 hours. The reaction mixture was cooled down, concentrated to half, filtered off, solid was washed with 25 ml carbontetrachloride. The filtrate was concentrated to give 4 g crude product, containing about 20% unreacted starting material. This was used for next step without purification. | |
1.9 g | With N-Bromosuccinimide; dibenzoyl peroxide; In tetrachloromethane; for 10h;Reflux; | 2-Methyl-4-nitro - benzoic acid methyl ester (3.0 g, 15 mmol) wasdissolved in carbon tetrachloride (50 mL), and then were added N- bromosuccinimide (3.0 g, 17 mmol) and benzoyl peroxide (100mg, 0.4 mmol), the addition was complete the reaction was refluxed for 10hours. Completion of the reaction, the reaction solution was cooled toroom temperature, filtered, and the filtrate was washed with saturated sodiumbicarbonate solution and water, dried over anhydrous sodium sulfate, filteredand concentrated. Was purified by silica gel column chromatography usingconcentrated to give the intermediate 2-bromomethyl-4-nitro - benzoic acidmethyl ester (pale yellow solid, 1.9 g). |
With N-Bromosuccinimide; dibenzoyl peroxide; In tetrachloromethane; for 2h;Reflux; | Compound I (1.95 g, 10.0 mmol) was dissolved in carbon tetrachloride (20 mL), and NBS (2.14 g, 12.0 mmol, 1.2 eq) and benzoyl peroxide (0. 024 g, 0.1 mmol, 0.1 eq) was added and the mixture was heated to reflux for 2 h. At the end of the reaction, the temperature was lowered and the solid was removed by suction filtration. The mother liquor was evaporated to dryness to give Compound II in a yield of 95%. | |
With N-Bromosuccinimide; dibenzoyl peroxide; In chloroform; at 65℃; for 5h;Inert atmosphere; Schlenk technique; Reflux; | General procedure: To a solution of 6.0 g (0.04 mol) of methyl 2-methylbenzoate derivatives in 38 mL of chloroform, 7.5 g (0.042 mol) of N-bromosuccinimide and 0.078 g of benzoyl peroxide were added and carefully warmed up to 65 C until reaction started. Then the mixture was refluxed for 5 h. After cooling down to room temperature, the deposit of succinimide was filtered. The solvent was removed under reduced pressure and the crude product was used in the next step without further purification. To a solution of functionalized methyl 2-(bromomethyl)benzoate (6.55 mmol), substituted phenol (8.5 mmol), K3PO4 (16.4 mmol) and toluene 20 mL were added to Schlenk under argon. The resulting solution was stirred to 110 C for 5 h. The progress of the reaction was monitored by TLC. The mixture was extracted with EtOAc, washed with water, brine and the combined organic layers were dried over anhydrous Na2SO4and the solvent was removed under reduced pressure. The crude product was used in the next step without further purification. To the solution of the ester (0.015 mol) in MeOH (73 mL), was added 13 mL aqueous KOH (20%) and refluxed at 80C for 5 h. MeOH was removed and the aqueous phase was washed with DCM. After acidifying with HCl (10%) the deposit was collected and washed with water. |
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