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CAS No. : | 210824-69-4 | MDL No. : | MFCD09801033 |
Formula : | C7H8BrNO2S | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | CFMBNGJNYNLPDL-UHFFFAOYSA-N |
M.W : | 250.11 | Pubchem ID : | 18400117 |
Synonyms : |
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Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P362-P403+P233-P501 | UN#: | |
Hazard Statements: | H315-H319-H335 | Packing Group: | |
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 |
---|---|---|
With ammonia; water |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
9.0 g | In N,N-dimethyl-formamide at 20℃; for 4.5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
2.5 g | Stage #1: 3-bromo-4-methylaniline With hydrogenchloride In water at 20℃; for 0.0833333h; Stage #2: With sodium nitrite In water at -15 - -10℃; for 0.75h; Stage #3: With sulfur dioxide; ammonia more than 3 stages; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
48% | With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 80℃; for 0.75h; | Part A:4-Methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenesulfonamide To a solution of 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane)(48.8 g, 192 mmol) in 1,4-dioxane (500 mL) was added potassium acetate (43.6 g,444 mmol). The mixture was degassed for15 min, and then PdCl2(dppf) (10.82 g, 14.79 mmol) and3-bromo-4-methylbenzenesulfonamide (37 g, 148 mmol) were added. The mixture was heated at 80 °C for 45 min,and then cooled. To the mixture wasadded ice-cold water (100 mL), and the mixture was extracted with 1:1 EtOAc-hexanes(2 x 200 mL). The organic phase waswashed with brine, dried over anhydrous Na2SO4, andconcentrated in vacuo. The residue was purified by chromatography onsilica gel using EtOAc-hexanes (1:3) to give 4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenesulfonamide(21g, 48 % yield). |
With potassium acetate In 1,4-dioxane at 80℃; for 4h; | 106.2 Into a 100-mL flask under argon were added 3-bromo-4-methylbenzenesulfonamide (900 mg, 3.6 mmol), dichloro[1,1'-bis(diphenylphosphino)ferrocene]palladium (II) dichloromethane adduct (263 mg, 0.36 mmol), bis(pinacolato)diboron (1.371 g, 5.4 mmol), and 1,4-dioxane (18 mL), followed by potassium acetate (1.77 g, 18 mmol). The reaction was heated at 80° C. for 4 h. The cooled reaction was diluted with CH2Cl2 and washed with saturated aqueous NaHCO3 solution and brine; dried (MgSO4). After filtering via a pad of Celite, the filtrate was concentrated in vacuo and purified by CombiFlash (25% to 50% ethyl acetate in Hexane) to afford the title compound as a white solid. Found MS (ES+): 298.1 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In ethanol; dichloromethane | 69.b b b (1S,2R)-2-Methyl-4'-(2-hydroxy-1-methyl-4-pyridin-3-yl-butoxy)biphenyl-5-sulfonic acid amide Prepared according to the method described in Example 12b) from (1S,2R)-4-(2-hydroxy-1-methyl-4-pyridin-3-ylbutoxy)benzeneboronic acid (0.15 g, Example 33), 3-bromo-4-methylphenylsulfonic acid amide (0.25 g, Example 69a)), ethanol (3 ml), 2M aqueous sodium carbonate (0.5 ml) and tetrakis(triphenylphosphine)palladium (0) (0.03 g) with heating at 90° C. for 3 hours. After work-up, the residue was purified by normal-phase HPLC eluding with a gradient of 0-25% ethanol in dichloromethane to give the title compound as a foam (0.19 g). MS (APCI) 427 (M+H)+ 1H NMR (CDCl3) 8.48(1H, s); 8.44(1H, d); 7.78(1H, s); 7.77(1H, d); 7.57(1H, d); 7.39(1H, d); 7.25(1H, d); 7.21(2H, d); 6.93(2H, d); 5.00(2H, br.s); 4.40(1H, m); 3.87(1H, m); 2.95(1H, m); 2.75(1H, m); 2.33(3H, s); 1.85(2H, m), 1.33(3H, d). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With 1,3-dibromo-5,5-dimethylhydantoin; 3-Nitrobenzenesulfonic acid at 60℃; for 12h; regioselective reaction; | |
With bromine; iron(0) at 20℃; for 1h; | 106.1 To a mixture of p-toluenesulfonamide (2 g, 1.16 mmol) and iron (0.41 g, 7.36 mmol) was slowly added bromine (6 mL, 116 mmol). The resulting reddish brown solution was stirred at RT for 1 h. The reaction was carefully poured into ice-cold 1 M Na2S2O3 aqueous solution and extracted with CH2Cl2 (2×). The organic extracts were combined and washed with brine, dried (MgSO4), filtered, and concentrated in vacuo. CombiFlash purification (1% to 10% MeOH/CH2Cl2) afforded the title compound as a white solid. 1H NMR (DMSO-d6, 400 MHz): 7.98 (s, 1H), 7.71 (d, J=8 Hz, 1H), 7.55 (d, J=8 Hz, 1H), 7.54 (br s, 2H), 2.41 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,4-dioxane / 16 h / Inert atmosphere; Reflux 2: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 16 h / Reflux; Inert atmosphere 3: acetic acid / 16 h / Reflux; Inert atmosphere 4: dmap; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide 5: hydrogenchloride; Dihydroxy-isobutyl-boran / methanol; hexane; water |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,4-dioxane / 16 h / Inert atmosphere; Reflux 2.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 16 h / Reflux; Inert atmosphere 3.1: acetic acid / 16 h / Reflux; Inert atmosphere 4.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 1 h / 20 °C 4.2: 72 h / 20 °C 5.1: hydrogenchloride; Dihydroxy-isobutyl-boran / methanol; hexane; water / 16 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,4-dioxane / 16 h / Inert atmosphere; Reflux 2: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 16 h / Reflux; Inert atmosphere | ||
Multi-step reaction with 2 steps 1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 0.75 h / 80 °C 2: N-Bromosuccinimide; azobisisobutyronitrile / tetrachloromethane / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,4-dioxane / 16 h / Inert atmosphere; Reflux 2: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 16 h / Reflux; Inert atmosphere 3: acetic acid / 16 h / Reflux; Inert atmosphere 4: dmap; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,4-dioxane / 16 h / Inert atmosphere; Reflux 2.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 16 h / Reflux; Inert atmosphere 3.1: acetic acid / 16 h / Reflux; Inert atmosphere 4.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 1 h / 20 °C 4.2: 72 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,4-dioxane / 16 h / Inert atmosphere; Reflux 2: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 16 h / Reflux; Inert atmosphere 3: acetic acid / 16 h / Reflux; Inert atmosphere | ||
Multi-step reaction with 3 steps 1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 0.75 h / 80 °C 2: N-Bromosuccinimide; azobisisobutyronitrile / tetrachloromethane / Reflux 3: N,N-dimethyl-formamide / 12 h / 100 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,4-dioxane / 16 h / Inert atmosphere; Reflux 2.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 16 h / Reflux; Inert atmosphere 3.1: acetic acid / 16 h / Reflux; Inert atmosphere 4.1: sodium hydroxide / 16 h / 20 °C 4.2: 16 h / 40 °C | ||
Multi-step reaction with 4 steps 1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 0.75 h / 80 °C 2: N-Bromosuccinimide; azobisisobutyronitrile / tetrachloromethane / Reflux 3: N,N-dimethyl-formamide / 12 h / 100 °C 4: hydrogenchloride / methanol; water / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: N,N-dimethyl-formamide / 4.5 h / 20 °C 2: sodium carbonate; triphenylphosphine / palladium diacetate / ethanol; water; toluene / 5.25 h / Heating / reflux 3: hydrogenchloride / methanol; water / 1.25 h / Heating / reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: N,N-dimethyl-formamide / 4.5 h / 20 °C 2: sodium carbonate; triphenylphosphine / palladium diacetate / ethanol; water; toluene / 5.25 h / Heating / reflux 3: hydrogenchloride / methanol; water / 1.25 h / Heating / reflux 4: 1.75 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: N,N-dimethyl-formamide / 4.5 h / 20 °C 2: sodium carbonate; triphenylphosphine / palladium diacetate / ethanol; water; toluene / 5.25 h / Heating / reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 0.75 h / 80 °C 2: N-Bromosuccinimide; azobisisobutyronitrile / tetrachloromethane / Reflux 3: N,N-dimethyl-formamide / 12 h / 100 °C 4: hydrogenchloride / methanol; water / 20 °C 5: dmap; dicyclohexyl-carbodiimide / dichloromethane / 12 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium permanganate In lithium hydroxide monohydrate; <i>tert</i>-butyl alcohol at 80℃; for 6h; | 17.1 Step 1. Synthesis of 2-bromo-4-sulfamoylbenzoic acid (17-1) To a solution of 3-bromo-4-methylbenzenesulfonamide (2.5 g, 10 mmol) in /BuOH (25 mL) and H2O (25 mL) was added KMnCL (4.0 g, 25 mmol) at RT. The resulting reaction mixture was stirred at 80 °C for 6 h. After the reaction mixture was cooled to RT, 1 N HC1 was added to adjust the pH to 2. The aqueous phase was extracted with EtOAc, dried over Na2S04, and concentrated to afford 2-bromo-4- sulfamoylbenzoic acid as white solid. ESI-MS, m/z 279.9 (M+H)+. | |
With potassium permanganate In lithium hydroxide monohydrate; <i>tert</i>-butyl alcohol at 80℃; for 6h; | 17.1 Step 1. Synthesis of 2-bromo-4-sulfamoylbenzoic acid (17-1) To a solution of 3-bromo-4-methylbenzenesulfonamide (2.5 g, 10 mmol) in /BuOH (25 mL) and H2O (25 mL) was added KMnCL (4.0 g, 25 mmol) at RT. The resulting reaction mixture was stirred at 80 °C for 6 h. After the reaction mixture was cooled to RT, 1 N HC1 was added to adjust the pH to 2. The aqueous phase was extracted with EtOAc, dried over Na2S04, and concentrated to afford 2-bromo-4- sulfamoylbenzoic acid as white solid. ESI-MS, m/z 279.9 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: potassium permanganate / <i>tert</i>-butyl alcohol; lithium hydroxide monohydrate / 6 h / 80 °C 2: borane-THF / tetrahydrofuran / 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: potassium permanganate / <i>tert</i>-butyl alcohol; lithium hydroxide monohydrate / 6 h / 80 °C 2: borane-THF / tetrahydrofuran / 0 - 20 °C 3: toluene-4-sulfonic acid / tetrahydrofuran / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: potassium permanganate / <i>tert</i>-butyl alcohol; lithium hydroxide monohydrate / 6 h / 80 °C 2: borane-THF / tetrahydrofuran / 0 - 20 °C 3: toluene-4-sulfonic acid / tetrahydrofuran / 20 °C 4: anhydrous potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II) dichloromethane adduct / 1,4-dioxane / 6 h / 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: potassium permanganate / <i>tert</i>-butyl alcohol; lithium hydroxide monohydrate / 6 h / 80 °C 2.1: borane-THF / tetrahydrofuran / 0 - 20 °C 3.1: toluene-4-sulfonic acid / tetrahydrofuran / 20 °C 4.1: anhydrous potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II) dichloromethane adduct / 1,4-dioxane / 6 h / 80 °C 5.1: sodium hydride / tetrahydrofuran / 0.25 h / 0 °C 5.2: 1 h / 20 °C 5.3: 1 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: potassium permanganate / <i>tert</i>-butyl alcohol; lithium hydroxide monohydrate / 6 h / 80 °C 2: dichlorosulfoxide / 12 h / 70 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: potassium permanganate / <i>tert</i>-butyl alcohol; lithium hydroxide monohydrate / 6 h / 80 °C 2: dichlorosulfoxide / 12 h / 70 °C 3: anhydrous potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II) dichloromethane adduct / 1,4-dioxane / 12 h / 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: potassium permanganate / <i>tert</i>-butyl alcohol; lithium hydroxide monohydrate / 6 h / 80 °C 2: dichlorosulfoxide / 12 h / 70 °C 3: tetrahydrofuran / 1 h / 20 °C / Cooling |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: potassium permanganate / <i>tert</i>-butyl alcohol; lithium hydroxide monohydrate / 6 h / 80 °C 2: dichlorosulfoxide / 12 h / 70 °C 3: tetrahydrofuran / 1 h / 20 °C / Cooling 4: n-butyllithium / tetrahydrofuran / -78 - -76 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: potassium permanganate / <i>tert</i>-butyl alcohol; lithium hydroxide monohydrate / 6 h / 80 °C 2: dichlorosulfoxide / 12 h / 70 °C 3: tetrahydrofuran / 1 h / 20 °C / Cooling 4: n-butyllithium / tetrahydrofuran / -78 - -76 °C 5: sodium hydride |