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[ CAS No. 773134-43-3 ] {[proInfo.proName]}

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Chemical Structure| 773134-43-3
Chemical Structure| 773134-43-3
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Product Details of [ 773134-43-3 ]

CAS No. :773134-43-3 MDL No. :MFCD06204242
Formula : C9H9BrO4S Boiling Point : -
Linear Structure Formula :- InChI Key :OMTWUICAKUOXOV-UHFFFAOYSA-N
M.W : 293.13 Pubchem ID :53393139
Synonyms :

Safety of [ 773134-43-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P264-P270-P301+P312-P330 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 773134-43-3 ]

* 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.

  • Downstream synthetic route of [ 773134-43-3 ]

[ 773134-43-3 ] Synthesis Path-Downstream   1~66

  • 1
  • [ 773134-43-3 ]
  • [ 930-51-8 ]
  • [ 948306-18-1 ]
YieldReaction ConditionsOperation in experiment
With copper(l) iodide; triethylamine;bis-triphenylphosphine-palladium(II) chloride; at 80℃; for 3.0h; Intermediate 35; Preparation of 4-(cyclopropylethynyl)-2-(methylsulfonyl)benzoic acid; 4-Bromo-2-methanesulfonyl acid methyl ester (250 mg, 0.85 mmol) was dissolved in triethylamine (5 mL). To the mixture was added copper iodide (9.0 mg, 5 mol %), followed by PdCl2(PPh3)2 (32 mg, 5 mol %) and ethynylcyclopentane (0.135 ml, 1.0 mmol). The mixture was heated in a sealed pressure tube at 80 C. for 3 hours. After reaction completion, the triethylamine was removed under vacuum and the residue was dissolved in EtOAc and filtered through Celite. The organic layer was washed with water, brine, and dried (Na2SO4). After filtration and concentration under vacuum, the residue was purified by column chromatography on sililca gel using EtOAc-hexane (0-100% gradient) as eluent to give methyl 4-(cyclopropylethynyl)-2-(methylsulfonyl)benzoate (240 mg). The product was dissolved in 10 mL of MeOH and 10 mL of 2N LiOH and the mixture was refluxed overnight. The MeOH was evaporated and the basic layer was washed with EtOAc, acidified, and re-extracted with EtOAc. The organic layer was washed with brine, dried (Na2SO4), filtered and concentrated under vacuum to give the product (165 mg) as a beige solid. m/z=293 (M+1).
  • 2
  • [ 67-56-1 ]
  • 4-bromo-2-(methylsulphonyl)benzoic acid [ No CAS ]
  • [ 773134-43-3 ]
YieldReaction ConditionsOperation in experiment
95% With sulfuric acid; for 16.0h;Reflux; A solution of 4-bromo-2-(methylsulfonyl)benzoic acid SM 1 (2 g, 7.16 mmol) in MeOH(30 mL) was added H2504 (5 ml) stirred at reflux for 16 h. Quenched with water, extracted withEtOAc, washed with water and brine, concentrated under reduced pressure to obtain crude product,which was purified by combiflash (petroleum ether: ethyl acetate = 1:1) to give compound 1 (2.0 g,95%) as a white solid. LC-MS: m/z = 293.1/295.1 [M+H]
72% With sulfuric acid; for 120.0h;Reflux; A suspension of 4-bromo-2-(methylsulphonyl)benzoic acid (5.00 g; 17.9 mmol) in MeOH (100 ml) was treated with cone, sulphuric acid and the resulting mixture was heated at reflux for 5 days. The mixture was concentrated under reduced pressure, the residue was dissolved in EtOAc then washed with water, twice with NaHCO3 (sat) then with brine, dried on MgSO4, filtered and concentrated to give the title compound as a yellow solid (4.00 g, 72%). 1H NMR (300MHz, DMSO-d6) δ [ppm] 8.14 (1 H, d, J= 1.9 Hz), 8.08 (1 H, d, J= 1.9 Hz, 8.1 Hz), 7.73 (1 H, d, J= 8.1 Hz), 3.86 (3H, s), 3.42 (3H, s). HPLC (Condition A): Rt 3.54 min (HPLC purity 95.5%).
3.34 g With sulfuric acid;Reflux; [0204] Preparation Example 22: Preparation of 4-(1,1-dioxo-1λ6-isothiazolidin-2-yl)-2-methanesulfonylbenzoic acid[0205][0206] To 4-bromo-2-methanesulfonylbenzoic acid (5 g) were added methanol (45 mL) and concentrated sulfuric acid(1.8 mL), and the mixture was stirred with heating under reflux. After completion of the reaction, the solvent was evaporated,and the residue was neutralized with 1N aqueous sodium hydroxide solution, and the mixture was extracted withethyl acetate. The organic layer was washed with saturated brine, and the solvent was evaporated to give methyl 4-bromo-2-methanesulfonylbenzoate (3.34 g). To a mixture of the obtained methyl 4-bromo-2-methanesulfonylbenzoate (3.34EP 2 565 182 A127510152025303540455055g), tris(dibenzylideneacetone)dipalladium(0)-chloroform adduct (295 mg), 2-(dicyclohexylphosphino)biphenyl (399 mg),tripotassium phosphate (3.39 g) and benzophenonimine (2.5 mL) was added 1,2-dimethoxyethane (25 mL), and themixture was stirred with heating under reflux. After completion of the reaction, water was added to the reaction mixture,and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and the solventwas evaporated. The obtained residue was dissolved in tetrahydrofuran (26 mL), 1N hydrochloric acid (100 mL) wasadded, and the mixture was stirred at room temperature for 1 hr. The reaction mixture was neutralized with sodiumhydrogen carbonate, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturatedbrine, and the solvent was evaporated to give methyl 4-amino-2-methanesulfonylbenzoate (1.46 g). Using the obtainedmethyl 4-amino-2-methanesulfonylbenzoate (1.46 g) and 3-chloropropane-1-sulfonyl chloride (1.03 mL) and by thereaction and treatment in the same manner as in Preparation Example 16, the title compound (0.53 g) was obtained
  • 3
  • [ 773134-43-3 ]
  • [ 1240288-81-6 ]
YieldReaction ConditionsOperation in experiment
100% PREPARATION 746-Bromo-1-benzothiophen-3(2H)-one 1 ,1 -dioxideTo a solution of <strong>[773134-43-3]methyl 4-bromo-2-(methylsulfonyl)benzoate</strong> (774 mg, 2.64 mmol) in anhydrous THF (10 mL) was added NaH (60% in mineral, 11 1 mg, 2.77 mmol). The mixture was stirred at room temperature for 5 hr. The reaction was monitored by LCMS for completion. H2O (1 mL) was added to quench the reaction followed by the addition of aqueous hydrochloric acid (1N, 50 mL) and EtOAc (50 mL). The organic layer was separated, and the water layer was extracted with 2 X EtOAc. The combined organic layers were washed with brine, dried over sodium sulfate, filtered, and concentrated to give the title compound (689 mg, 100%) as a white solid.1H NMR (400 MHz, DMSO-d6) δ ppm 4.62 (s, 2H), 7.92 (d, J=8.34 Hz, 1 H), 8.14 (dd, J=8.21 , 1.14 Hz, 1 H), 8.53 (s, 1 H).
92% With sodium hydride; In tetrahydrofuran; at 20℃; for 2.0h; To a stirring solution of compound 1(1.7 g, 5.8 mmol) in dry THF (20 mL) was added NaH (139 mg, 5.8 mmol), then stirred at RT for 2 h. Quenched with water and HC1 (iN, 10 ml), extracted with EtOAc, concentrated under reduced pressure to obtain crude product, which was purified by combiflash (petroleum ether:ethyl acetate = 1:1) to give compound 2 (1.4 g, 92%) as ayellow solid. LC-MS: m/z = 26 1.0/263.0 [M+H]
With sodium hydride; In tetrahydrofuran; at 20℃; for 1.5h; A solution of <strong>[773134-43-3]methyl 4-bromo-2-(methylsulfonyl)benzoate</strong> (Intermediate 239; 4.00 g; 13.6 mmol) in anhydrous THF (60 ml) was treated with NaH (595 mg; 13.6 mmol) and stirred at RT for 1.5 h. The reaction was quenched with water. AcOEt and a 1 N solution of HCI in water were added and the phases were separated. The organic phase was washed with brine, dried on MgSO4, filtered and concentrated to give the title compound as a yellow solid (3.63 g).1H NMR (300MHz, DMSO-d6) δ [ppm] 8.55 (1 H, d, J= 1.7 Hz), 8.15 (1 H, d, J= 1.7 Hz, 8.2Hz), 7.93 (1 H, d, J= 8.2 Hz), 4.62 (2H, s). MS (ESI"): 261.0. HPLC (Condition A): Rt 2.56 min.
  • 4
  • [ 773134-43-3 ]
  • [ 1240288-82-7 ]
  • 5
  • [ 773134-43-3 ]
  • [ 1240288-83-8 ]
  • 6
  • [ 773134-43-3 ]
  • [ 1240288-85-0 ]
  • 7
  • [ 773134-43-3 ]
  • [ 1240288-87-2 ]
  • 8
  • [ 773134-43-3 ]
  • [ 1240288-89-4 ]
  • 9
  • [ 773134-43-3 ]
  • [ 1240288-91-8 ]
  • 10
  • [ 773134-43-3 ]
  • [ 1240288-93-0 ]
  • 11
  • [ 773134-43-3 ]
  • [ 1240288-96-3 ]
  • 12
  • [ 773134-43-3 ]
  • [ 1240288-98-5 ]
  • 13
  • [ 773134-43-3 ]
  • [ 1240289-02-4 ]
  • 14
  • [ 773134-43-3 ]
  • [ 75-16-1 ]
  • [ 918350-13-7 ]
YieldReaction ConditionsOperation in experiment
54.2% PREPARATION 762-(4-bromo-2-(methylsulfonyl)phenyl)propan-2-ol To a cooled (0C) solution of 4-bromo-2-(methylsulfonyl)benzoate (603 mg, 2.06 mmol) in THF (12 mL) was added a THF solution of MeMgBr (3M, 2.06 mmL, 6.17 mmol). The reaction was stirred at room temperature for overnight. LCMS showed the starting material was consumed completely. The reaction was quenched with the slow addition of saturated aqueous NH4CI (10 mL), diluted with EtOAc (50 mL) and water (25 mL), extracted twice more with EtOAc (35 mL), dried over sodium sulfate, filtered,concentrated, and purified with a silica gel column by ISCO CombiFlashchromatography eluting with 0%-30% EtOAc/Heptane to give the title compound (327 mg, 54.2%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.62 (s, 6 H), 3.44 (s, 3 H), 5.51 (s, 1 H), 7.58 (d, J=8.59 Hz, 1 H), 7.84 (dd, J=8.59, 2.27 Hz, 1 H), 8.20 (d, J=2.27 Hz, 1 H).
  • 15
  • [ 773134-43-3 ]
  • [ 1346818-94-7 ]
  • 16
  • [ 773134-43-3 ]
  • (5-bromo-2-(methylsulfonyl)phenyl)methanol [ No CAS ]
YieldReaction ConditionsOperation in experiment
PREPARATION 99a(4-Bromo-2-(methylsulfonyl)phenyl)methanolTo a stirring solution of <strong>[773134-43-3]methyl 4-bromo-2-(methylsulfonyl)benzoate</strong> (1000 mg, 3.41 mmol) in THF (20 mL) at -78C was added DIBAL-H solution (1.0 M in hexanes, 7.50 ml, 2.20 equiv.) dropwise. The mixture was stirred for 15 min and then gradually warmed to room temperature and stirred for another 4 hour. LCMS indicated clean conversion of the starting material to the product. The reaction was quenched with sodiumbicarbonate, and then concentrated to dryness. The resulting solids were stirred with DCM (100 ml) for 1 hour and then filtered. The solids were rinsed with EtOAc until the rinse was free of product. The combined filtrate were dried over sodium sulfate, concentrated to dryness to give the desired product (788 mg)1H NMR (400 MHz, CDCI3) δ ppm 8.19 (d, J=2.02 Hz, 1 H), 7.78 (dd, J=8.08, 2.02 Hz, 1 H), 7.47 (d, J=8.08 Hz, 1 H), 4.93 (d, J=6.57 Hz, 2 H), 3.20 (s, 3 H), 2.90 (t, J=6.69 Hz, 1 H).
  • 17
  • [ 773134-43-3 ]
  • [ 1346816-62-3 ]
  • 18
  • [ 773134-43-3 ]
  • [ 1346123-21-4 ]
YieldReaction ConditionsOperation in experiment
1.46 g [0204] Preparation Example 22: Preparation of 4-(1,1-dioxo-1λ6-isothiazolidin-2-yl)-2-methanesulfonylbenzoic acid[0205][0206] To 4-bromo-2-methanesulfonylbenzoic acid (5 g) were added methanol (45 mL) and concentrated sulfuric acid(1.8 mL), and the mixture was stirred with heating under reflux. After completion of the reaction, the solvent was evaporated,and the residue was neutralized with 1N aqueous sodium hydroxide solution, and the mixture was extracted withethyl acetate. The organic layer was washed with saturated brine, and the solvent was evaporated to give methyl 4-bromo-2-methanesulfonylbenzoate (3.34 g). To a mixture of the obtained methyl 4-bromo-2-methanesulfonylbenzoate (3.34EP 2 565 182 A127510152025303540455055g), tris(dibenzylideneacetone)dipalladium(0)-chloroform adduct (295 mg), 2-(dicyclohexylphosphino)biphenyl (399 mg),tripotassium phosphate (3.39 g) and benzophenonimine (2.5 mL) was added 1,2-dimethoxyethane (25 mL), and themixture was stirred with heating under reflux. After completion of the reaction, water was added to the reaction mixture,and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and the solventwas evaporated. The obtained residue was dissolved in tetrahydrofuran (26 mL), 1N hydrochloric acid (100 mL) wasadded, and the mixture was stirred at room temperature for 1 hr. The reaction mixture was neutralized with sodiumhydrogen carbonate, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturatedbrine, and the solvent was evaporated to give methyl 4-amino-2-methanesulfonylbenzoate (1.46 g). Using the obtainedmethyl 4-amino-2-methanesulfonylbenzoate (1.46 g) and 3-chloropropane-1-sulfonyl chloride (1.03 mL) and by thereaction and treatment in the same manner as in Preparation Example 16, the title compound (0.53 g) was obtained
  • 19
  • methyl 4-bromo-2-(methylthio)benzoate [ No CAS ]
  • [ 773134-43-3 ]
YieldReaction ConditionsOperation in experiment
99% With Oxone; In methanol; water; at 0 - 60℃; for 16.0h; A solution of oxone (1.17 kg, 3.79 mol, 5.50 eq.) in DMW (4.50 L) was added to a stirred solution of methyl 4-bromo-2-(methylthio)benzoate (103) (180.0 g, 589 mmol, 1.0 eq.) in methanol (3.60 L) at 0 C. The reaction mixture was stirred at 60 C. for 16 h. The progress of the reaction was monitored by TLC (30% EtOAc in n-hexane). About 40% of the solvent was removed by distillation then chilled DMW (4.50 L) was added to the reaction mixture and stirred for 15 minutes. The precipitated solid was collected by filtration to afford the wet product 104. The wet product was dried in a vacuum oven at below 50 C. to afford dried intermediate 104 (200 g, 99.0%) as an off white solid. 1HNMR (300 MHz, DMSO-d6): δ 8 8.19-8.02 ppm (m, 2H), 7.73 ppm (d, J=8.1 Hz, 1H), 3.87 ppm (s, 3H), 3.42 ppm (s, 3H). MS (ESI): m/z 311.5 (M+18).
7.9 g With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 20℃; [00244] To a solution of methyl 4-bromo-2-(methylthio)benzoate (crude 10.8 g, 0.041 mol) in CH2C12 (500 mL) was added m-CPBA (21.4 g, 0.124 mol). The mixture was stirred at rt overnight. The mixture was washed successively with sat. Na25203 solution (300 mL), sat. NaHCO3 solution (300 mL) and brine (300 mL), dried over anhydrous Na2504, filtered and concentrated under reduced pressure. The residue was purified by chromatography column on silica gel eluting with petroleum ether: EtOAc 3:1 to afford methyl4-bromo-2- (methylsulfonyl) benzoate (7.9 g, 65%) as a white solid. 1H NMR (CDC13): ö 8.28 (d, I = 2.0 Hz, 1H), 7.82 (dd, I = 2.0, 8.4 Hz, 1H), 7.60 (d, I = 8.0 Hz, 1H), 3.97 (s, 3H), 3.37 (s, 3H).
32.8 g With Oxone; In 1,4-dioxane; water; at 20℃; The crude 183-3 (20.0 g) was dissolved in dioxane/water (400 mL/200 mL), added with potassium hydrogen persulfate (Oxone , 142 g, 231.0 mmol) in batches, and stirred overnight at room temperature. The reaction solution was filtered, and washed with ethyl acetate. The filtrate was concentrated, diluted with water and extracted with ethyl acetate. The combined organic phase was washed with saturated sodium thiosulfate solution, dried over anhydrous sodium sulfate, and concentrated to obtain 183-4 (23.8 g) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ 8.13 (d, J = 1.8 Hz, 1H), 8.08 (dd, J = 8.1, 1.9 Hz, 1H), 7.72 (d, J = 8.2 Hz, 1H), 3.87 (s, 3H), 3.42 (s, 3H).
  • 20
  • [ 773134-43-3 ]
  • (R)-(2-(4-(4-(hydroxymethyl)-3-(methylsulfonyl)phenyl)-2-isopropylpiperazin-1-yl)-4-(trifluoromethyl)pyrimidin-5-yl)methanol [ No CAS ]
  • 21
  • [ 773134-43-3 ]
  • (R)-(2-(2-isopropyl-4-(3-(methylsulfonyl)-4-(4-methylthiazol-2-yl)phenyl)piperazin-1-yl)-4-(trifluoromethyl)pyrimidin-5-yl)methanol [ No CAS ]
  • 22
  • [ 773134-43-3 ]
  • (2-(methylsulfonyl)-4-(3-phenyl-4-((6-(trifluoromethyl)pyridin-3-yl)methyl)piperazin-1-yl)phenyl)methanol [ No CAS ]
  • 23
  • [ 773134-43-3 ]
  • (4-((S)-3-isopropyl-4-(((3R,6S)-6-(trifluoromethyl)tetrahydro-2H-pyran-3-yl)methyl)piperazin-1-yl)-2-(methylsulfonyl)phenyl)methanol [ No CAS ]
  • (4-((S)-3-isopropyl-4-(((3R,6R)-6-(trifluoromethyl)tetrahydro-2H-pyran-3-yl)methyl)piperazin-1-yl)-2-(methylsulfonyl)phenyl)methanol [ No CAS ]
  • 24
  • [ 773134-43-3 ]
  • (4-((S)-3-isopropyl-4-(((3S,6S)-6-(trifluoromethyl)tetrahydro-2H-pyran-3-yl)methyl)piperazin-1-yl)-2-(methylsulfonyl)phenyl)methanol [ No CAS ]
  • (4-((S)-3-isopropyl-4-(((3S,6R)-6-(trifluoromethyl)tetrahydro-2H-pyran-3-yl)methyl)piperazin-1-yl)-2-(methylsulfonyl)phenyl)methanol [ No CAS ]
  • 25
  • [ 773134-43-3 ]
  • methyl (R)-4-(3-isopropylpiperazin-1-yl)-2-(methylsulfonyl)benzoate [ No CAS ]
  • 26
  • [ 773134-43-3 ]
  • ethyl (R)-2-(2-isopropyl-4-(4-(methoxycarbonyl)-3-(methylsulfonyl)phenyl)piperazin-1-yl)-4-(trifluoromethyl)pyrimidine-5-carboxylate [ No CAS ]
  • 27
  • [ 773134-43-3 ]
  • 4-bromo-2-(methylsulphonyl)benzoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% With water; sodium hydroxide; In methanol; at 20℃; A solution of NaOH (192.0 g, 4.80 mol, 7.0 equiv.) in water (2.01 L) was added to a stirred solution of <strong>[773134-43-3]methyl 4-bromo-2-(methylsulfonyl)benzoate</strong> (104) (201.0 g, 0.68 mol, 1.0 equiv.) in methanol (2.01 L). The reaction mixture was stirred at RT for 3.0 h. The progress of the reaction was monitored by TLC (20% MeOH in DCM). The solvent was removed under reduced pressure. Ice cold DMW (1.5 L) was added to the residue and 5N HCl was added to adjust the pH to ˜5. The precipitated solid was collected by filtration, washed with chilled water (1000 mL), dried to afford intermediate 105 (155.0 g, 81.0%) as an off white solid. 1H NMR (300 MHz, DMSO-d6): 8.09 ppm (d, J=2.0 Hz, 1H), 8.04 ppm (dd, J=8.2, 2.0 Hz, 1H), 7.70 ppm (d, J=8.2 Hz, 1H), 3.44 ppm (s, 3H). MS (ESI): m/z 278.8 (M-1)
With water; sodium hydroxide; In methanol; at 60℃; for 4.0h; [00246] To a solution of <strong>[773134-43-3]methyl 4-bromo-2-(methylsulfonyl)benzoate</strong> (1.0 g, 3.4 mmol) in methanol (3 mL) and H20 (1 mL) was added NaOH (410 mg, 10.2 mmol). The mixture was stirred at 60 C for 4 h. The mixture was concentrated under reduced pressure and the mixture was adjusted to pH = 4 with iN HC1 solution. The aqueous layer was extracted with EtOAc (3 X 20 mL). The combined organic layers were washed with brine, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to afford crude 4- bromo-2-(methylsulfonyl)benzoic acid (crude 800 mg, 84%) as a white solid, which was used for the next step directly without further purification. LC-MS tR = 0.850 mm in 2 mm chromatography. MS (ESI) m/z 262.9 [M + H - H20]+, 300.9 [M + Na]+. 1H NMR (DMSO-d6): ö 8.08 (d, I = 2.0 Hz, 1H), 8.02 (dd, I = 2.0, 8.0 Hz, 1H), 7.68 (d, I = 8.4 Hz, 1H), 3.42 (s, 3H).
  • 28
  • [ 773134-43-3 ]
  • 4-bromo-2-(methylsulfonyl)benzamide [ No CAS ]
  • 29
  • [ 773134-43-3 ]
  • 4-bromo-2-(methylsulfonyl)benzothioamide [ No CAS ]
  • 30
  • [ 773134-43-3 ]
  • 2-(4-bromo-2-(methylsulfonyl)phenyl)-4-methylthiazole [ No CAS ]
  • 31
  • [ 773134-43-3 ]
  • (R)-ethyl 2-(2-isopropyl-4-(3-(methylsulfonyl)-4-(4-methylthiazol-2-yl)phenyl)piperazin-1-yl)-4-(trifluoromethyl)pyrimidine-5-carboxylate [ No CAS ]
  • 32
  • [ 773134-43-3 ]
  • (S)-methyl 4-(3-isopropylpiperazin-1-yl)-2-(methylsulfonyl)benzoate [ No CAS ]
  • 33
  • [ 773134-43-3 ]
  • methyl 4-((3S)-3-isopropyl-4-(6-(trifluoromethyl)tetrahydro-2H-pyran-3-carbonyl)piperazin-1-yl)-2-(methylsulfonyl)benzoate [ No CAS ]
  • 34
  • [ 773134-43-3 ]
  • 2-phenyl-1-((6-(trifluoromethyl)pyridin-3-yl)methyl)piperazine [ No CAS ]
  • methyl 2-(methylsulfonyl)-4-(3-phenyl-4-((6-(trifluoromethyl)pyridin-3-yl)methyl)piperazin-1-yl)benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
47% With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In toluene; for 8.0h;Inert atmosphere; Reflux; [00318] To a solution of <strong>[773134-43-3]methyl 4-bromo-2-(methylsulfonyl)benzoate</strong> (200 mg, 0.68 mmol) in toluene (6 mL) was added 2-phenyl-1-((6-(trifluoromethyl)pyridin-3- yl)methyl)piperazine (219 mg, 0.68 mmol), BINAP (31 mg, 0.068 mmol), Pd2dba3 (60 mg, 0.068 mmol) and Cs2CO3 (665 mg, 2.04 mmol). The mixture was stirred at reflux for 8 h under N2. The mixture was filtered, the filtrate was added with water (10 mL) and extracted with EtOAc (3 X 10 mL). The combined organic layers were washed with brine, dried over anhydrous Na2504, filtered and concentrated under reduced pressure. The residue was purified by preparative TLC to give methyl 2- (methylsulfonyl)-4- (3-phenyl-4- ((6- (trifluoromethyl)pyridine-3-yl)methyl)piperazin- 1 -yl)benzoate (171 mg, 47%) as a yellow oil.
  • 35
  • [ 674792-05-3 ]
  • [ 773134-43-3 ]
  • (S)-tert-butyl 2-isopropyl-4-(4-(methoxycarbonyl)-3-(methylsulfonyl)phenyl)piperazine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; XPhos; In toluene; at 100℃;Inert atmosphere; [00339] To a solution of (5)-tert-butyl 2-isopropylpiperazine-1-carboxylate (400 mg, 1.76 mmol) in anhydrous toluene (10 mL) was added methyl 4-bromo-2-(methylsulfonyl)benzoate (1.03 g, 4.8 mmol), X-phos (80 mg, 0.17 mmol), Cs2CO3 (1.50 g, 4.62 mmol) and Pd2(dba)3 (200 mg, 0.22 mmol) under N2. The reaction mixture was stirred at 100 oC overnight. The reaction was quenched with water (20 mL), and extracted with EtOAc (4 X 20 mL). The combined organic layers were dried over anhydrous Na2504, filtered, concentrated and then purified by preparative TLC with petroleum ether / EtOAc 5/1 to afford (5)-tert-butyl 2- isopropyl-4- (4- (methoxycarbonyl)-3- (methylsulfonyl)phenyl)piperazine- 1 -carboxylate (500 mg, 65% yield) as a grey solid.
  • 36
  • [ 674792-04-2 ]
  • [ 773134-43-3 ]
  • tert-butyl (R)-2-isopropyl-4-(4-(methoxycarbonyl)-3-(methylsulfonyl)phenyl)piperazine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; XPhos; In toluene; at 100℃; for 2h;Inert atmosphere; Sealed tube; [00196] To a mixture of amine 7 (740 mg, 3.0 mmol), bromide 8 (1.05 g, 3.6 mmol), Xphos (160, 0.33 mmol) and Cesium carbonate (2.93 g, 9.0 mmol) in toluene (7 mL) was added Pd2(dba)3 (140 mg, 0.15 mmol). The mixture was purged with nitrogen and the tube was sealed. It was heated in an oil bath at 100C for 10 h. After cooling to rt, the reaction mixture was filtered and concentrated. The residue was purified by silica gel chromatography (EtOAc/hexanes = 40/60) to afford the coupling product 9 (1.17 g, 86% yield). LC-MS tR = 1.66 mm in 2 mm chromatography, MS (ESI) m/z 463 [M + 231+.
  • 37
  • [ 179232-29-2 ]
  • [ 773134-43-3 ]
  • 38
  • [ 773134-43-3 ]
  • ethyl (S)-2-(2-isopropyl-4-(4-(methoxycarbonyl)-3-(methylsulfonyl)phenyl)piperazin-1-yl)-4-(trifluoromethyl)pyrimidine-5-carboxylate [ No CAS ]
  • 39
  • [ 773134-43-3 ]
  • (S)-(2-(4-(4-(hydroxymethyl)-3-(methylsulfonyl)phenyl)-2-isopropylpiperazin-1-yl)-4-(trifluoromethyl)pyrimidin-5-yl)methanol [ No CAS ]
  • 40
  • [ 773134-43-3 ]
  • N-benzyl-2-{6-bromo-1,1,2',5'-tetraoxo-2H-spiro[1λ6-benzothiophene-3,4'-imidazolidine]-1'-yl}-N-[(1S)-1-cyclopropylethyl]acetamide [ No CAS ]
  • 41
  • [ 773134-43-3 ]
  • N-benzyl-N-[(1S)-1-cyclopropylethyl]-2-[1,1,2',5'-tetraoxo-6-(1H-pyrazol-3-yl)-2H-spiro[1λ6-benzothiophene-3,4'-imidazolidine]-1'-yl]acetamide [ No CAS ]
  • 42
  • [ 773134-43-3 ]
  • 2-(6-bromo-1,1-dioxido-2',5'-dioxo-1'H-spiro[1-benzothiophene-3,4'-imidazolidin]-1'-yl)-N-[(1S)-1-cyclopropylethyl]-N-(4-fluorobenzyl)acetamide [ No CAS ]
  • 43
  • [ 773134-43-3 ]
  • 6-bromo-2H-spiro[benzo[b]thiophene-3,4'-imidazolidine]-2',5'-dione-1,1-dioxide [ No CAS ]
  • 44
  • [ 773134-43-3 ]
  • tert-butyl (R)-6-isopropyl-2,6-dihydropyrrolo[3,4-c]pyrazole-5(4H)-carboxylate [ No CAS ]
  • C22H29N3O6S [ No CAS ]
  • 45
  • [ 773134-43-3 ]
  • C16H19N3O2 [ No CAS ]
  • C25H27N3O6S [ No CAS ]
  • 46
  • [ 773134-43-3 ]
  • C23H27F3N4O6S [ No CAS ]
  • 47
  • [ 773134-43-3 ]
  • (R)-(2-(4-(4-(hydroxymethyl)-3-(methylsulfonyl)phenyl)-2-isopropyl-piperazin-1-yl)-4- (trifluoromethyl)pyrimidin-5-yl)methyl 6-((tert-butoxycarbonyl)amino)hexanoate [ No CAS ]
  • 48
  • [ 773134-43-3 ]
  • (R)-(2-(4-(4-(hydroxymethyl)-3-(methylsulfonyl)phenyl)-2-isopropylpiperazin-1-yl)-4-methyl) (trifluoropyrimidin-5-yl)methyl 6-(3-(3',6'-dihydroxy-2-oxo-2H-spiro[benzofuran-3,9'-xanthen]-6-yl)thioureido)hexanoate [ No CAS ]
  • 49
  • [ 773134-43-3 ]
  • [ 773873-27-1 ]
YieldReaction ConditionsOperation in experiment
With methanol; lithium borohydride; at 0 - 80℃; To a solution of <strong>[773134-43-3]methyl 4-bromo-2-(methylsulfonyl)benzoate</strong> (3.00 g, 10.2 mmol) in MeOH (20 mL) was added L1BH4 (4.00 g, 100 mmol) slowly at 0C. The mixture was stirred at 80C overnight. Water (40 mL) was added slowly under cooling with an ice bath and the mixture was extracted with EA (3 x 30 mL). The combined organic layer was washed with brine (30 mL), dried over Na2S04 filtered and concentrated under reduced pressure to give compound P25a as a pale yellow solid, which was directly used in the next step.
  • 50
  • [ 773134-43-3 ]
  • [ 1161500-36-2 ]
  • 51
  • [ 773134-43-3 ]
  • C28H35BN2O5 [ No CAS ]
  • tert-butyl-2’-(4’-(methoxycarbonyl)-3’-(methylsulfonyl)-[1,1'-biphenyl]-3-yl)- 2-oxospiro [indoline-3,3'-pyrrolidine]-1'-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
44% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate; at 85℃;Inert atmosphere; General procedure: Compounds 4-1 to 4-12, 4-15 to 4-20 were synthesized by thegeneral method described here. Bromobenzene (0.22 mmol, 1.1equiv.), potassium carbonate (30 mg, 0.22 mmol, 1.1 equiv.) andPd(dppf)2Cl2 (7 mg, 0.01 mmol, 0.05 euiqv.) were added under anN2 atmosphere to a solution of S-3 (100 mg, 0.2 mmol, 1.0 equiv.) in3 mL 2,4-dioxane, and the mixture was stirred at 85 C overnight.The mixture was cooled in an ice bath, and this was followed byaddition of saturated NH4Cl to quench the reaction. The mixturewas extracted with 20 mL EtOAc thrice, washed with brine, driedover anhydrous Na2SO4, filtered and concentrated in vacuo. Theresiduewas purified by silica gel flash chromatography (Biotage SP-1, 20 g SiO2 column, gradient elution from 20 to 60% EtOAc) toafford the derivatives 4-1 to 4-12, 4-15 and 4-20.
  • 52
  • [ 773134-43-3 ]
  • tert-butyl 2'-isopropyl-2-oxospiro[indoline-3,3'-pyrrolidine]-1'-carboxylate [ No CAS ]
  • tert-butyl 2'-isopropyl-1-(4-(methoxycarbonyl)-3-(methylsulfonyl)phenyl)-2-oxospiro[indoline-3,3'-pyrrolidine]-1'-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
46% With copper(l) iodide; potassium carbonate; N,N`-dimethylethylenediamine; In toluene; at 90℃;Inert atmosphere; General procedure: 1-Chloro-3-iodobenzene (3.4 mL, 27.5 mmol, 1.1 equiv.) or thearyl bromide (R1Br, for 7 and 9), potassium carbonate (3.8 g,27.5 mmol, 1.1 equiv.) N,N-dimethylethane-1,2-diamine (0.15 mL,1.25 mmol, 0.05 equiv.) and CuI (240 mg, 1.25 mmol, 0.05 equiv.)were added to a solution of 1 (8.3 g, 25 mmol, 1 equiv.) in toluene(100 mL) under an N2 atmosphere, and stirred at 90 C overnight.The mixture was then diluted with EtOAc, and washed with saturatedaq. NH4Cl, dried over Na2SO4, filtered and concentrated invacuo to afford the crude product, which was purified by flashchromatography (Biotage, gradient elution from 20 to 50% EtOAc)to afford the product. Tert-butyl-1-(3-chlorophenyl)-20-isopropyl-2-oxospiro [indoline-3,30-pyrrolidine]-10-carboxylate (S-2) as awhite solid (6.4 g, 58%).
  • 53
  • [ 116209-30-4 ]
  • [ 773134-43-3 ]
  • 54
  • [ 773134-43-3 ]
  • 4-bromo-2-(methylsulfonyl)benzoyl chloride [ No CAS ]
  • 55
  • [ 773134-43-3 ]
  • 7-(4-bromo-2-(methylsulfonyl)benzamido)-2,3-dihydrobenzo[b][1,4]dioxine-6-carboxylic acid [ No CAS ]
  • 56
  • [ 20776-50-5 ]
  • [ 773134-43-3 ]
  • 57
  • [ 112704-79-7 ]
  • [ 773134-43-3 ]
  • 58
  • [ 773134-43-3 ]
  • C12H10N2O3S [ No CAS ]
  • 59
  • [ 773134-43-3 ]
  • C14H12N4O4S [ No CAS ]
  • 60
  • [ 773134-43-3 ]
  • C26H21F4N5O6S [ No CAS ]
  • 61
  • [ 773134-43-3 ]
  • C26H21F4N5O6S [ No CAS ]
  • C26H21F4N5O6S [ No CAS ]
  • 62
  • [ 773134-43-3 ]
  • [ 761446-44-0 ]
  • C13H14N2O4S [ No CAS ]
YieldReaction ConditionsOperation in experiment
5.16 g With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate; In 1,4-dioxane; water; at 100℃; for 3.0h; 183-4 (6.0 g), 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole 182-3a (5.12 g, 24.61 mmol), sodium carbonate (6.51 g, 61.42 mmol) and [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium dichloromethane complex (837 mg, 1.02 mmol) were dissolved in 1,4-dioxane/water (60 mL/50 mL), and heated to 100 C to react for 3h. The reaction solution was cooled to room temperature, concentrated, poured into water and extracted with dichloromethane. The combined organic phase was washed with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated. The crude was purified by silica gel column chromatography to obtain 183-5 (5.16 g) as a yellow solid. 1H-NMR (400 MHz, DMSO-d6) δ 8.37 (s, 1H), 8.11 (d, J = 1.7 Hz, 1H), 8.01 (d, J = 0.7 Hz, 1H), 7.98 (dd, J = 8.0, 1.8 Hz, 1H), 7.72 (d, J= 8.0 Hz, 1H), 3.87 (s, 3H), 3.84 (s, 3H), 3.39 (s, 3H).
  • 63
  • [ 773134-43-3 ]
  • 2-(4-bromo-2-(methylsulfonyl)phenyl)-7,8-dihydro-4H-[1,4]dioxino [2′,3′:4,5]benzo[1,2-d][1,3]oxazin-4-one [ No CAS ]
  • 64
  • [ 773134-43-3 ]
  • 2-(2-(methylsulfonyl)-4-vinylphenyl)-7,8-dihydro-4H-[1,4]dioxino[2',3':4,5]benzo[1,2-d][1,3]oxazin-4-one [ No CAS ]
  • 65
  • [ 773134-43-3 ]
  • 3-(methylsulfonyl)-4-(4-oxo-7,8-dihydro-4H-[1,4]dioxino[2',3':4,5]benzo[1,2-d][1,3]oxazin-2-yl)benzaldehyde [ No CAS ]
  • 66
  • [ 773134-43-3 ]
  • 2-(4-(hydroxymethyl)-2-(methylsulfonyl)phenyl)-7,8-dihydro-4H-[1,4]dioxino[2',3':4,5]benzo[1,2-d][1,3]oxazin-4-one [ No CAS ]
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