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[ CAS No. 648905-63-9 ] {[proInfo.proName]}

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Chemical Structure| 648905-63-9
Chemical Structure| 648905-63-9
Structure of 648905-63-9 * Storage: {[proInfo.prStorage]}
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Product Details of [ 648905-63-9 ]

CAS No. :648905-63-9 MDL No. :MFCD06657804
Formula : C16H26BNO4S Boiling Point : -
Linear Structure Formula :- InChI Key :NUVAQUSOEGIPTR-UHFFFAOYSA-N
M.W : 339.26 Pubchem ID :16414185
Synonyms :

Safety of [ 648905-63-9 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P264-P271-P280-P302+P352-P304+P340+P312-P305+P351+P338-P332+P313-P337+P313-P362-P403+P233-P405-P501 UN#:
Hazard Statements:H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 648905-63-9 ]

* 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 [ 648905-63-9 ]

[ 648905-63-9 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 93281-65-3 ]
  • [ 73183-34-3 ]
  • [ 648905-63-9 ]
YieldReaction ConditionsOperation in experiment
86% With potassium acetate In dichloromethane; dimethyl sulfoxide at 90℃; for 7.5h; 8.P' A 25 mL DMSO mixture of 4-bromo-N-tert-butyl-benzenesulfonamide (CAS 93281-65-3) (2000 mg, 6.84 mmol), bis (pinacolato)diboron mg, 8.21 mmol), [1,1 bis(diphenylphosphino)ferrocene]dichloropalladium(II) complex with CH2C12 (1:1) (175 mg, 240 mmol), and KOAc (2020 mg, 20.5 mmol) is stirred under N2 at 90° C for 7.5 hours. Reaction mixture is allowed to cool, is diluted with H20 and is extracted with CH2C12. The CH2C12 extract is washed with H20 and brine, dried (Na2S04) and evaporated. The crude product is purified by silica-gel column chromatography (gradient: 100% CH2C12 to 5% EtOAc/ CH2C12) give the intermediate N-tert-butyl-4-(4,4,5,5- tetramethyl- [1,3,2]dioxaborolan-2-yl)-benzenesulfonamide (2000 mg, 86% yield). (MS (ES-) 256 (boronic acid).
86% Stage #1: 4-bromo-N-(tert-butyl)benzenesulfonamide; bis(pinacol)diborane With potassium acetate In dimethyl sulfoxide at 20 - 90℃; for 7.5h; Stage #2: With water In dimethyl sulfoxide 20 Place t-butylamine (4.32 mL, 41.1 mmol), triethylamine (8.15 mL, 58.7 mmol) and dichloromethane (75 mL) in a 3-neck round bottom flask. Cool this stirring solution to 0°C and add a solution of 4-bromobenzenesulfonyl chloride (10.0 g, 39. 1 mmol) in dichloromethane (50 mL). Add additional dichloromethane (25 mL) and stir the reaction overnight, allowing it to warm to ambient temperature. Evaporate the reaction in vacuo. Suspend the resulting white solid in ethyl acetate and filter it. Concentrate the filtrate in vacuo and purify the resulting residue by flash chromatography (silica gel ; 50%-80% gradient CH2C12 in hexanes) to provide 9.85 g of 4-bromo-N-tert-butyl- benzenesulfonamide (86%). Place 4-bromo-N-tert-butyl-benzenesulfonamide (2.00 g, 6. 84 mmol), bis (pinacolato) diboron (2.09 g, 8.21 mmol), PdC12 (dppf) 2'CH2CI2 (175 mg, 0.24 mmol), potassium acetate (2.02 g, 20.5 mmol) and anhydrous dimethyl sulfoxide (25 mL) in a round bottom flask. Put the reaction in an oil bath and stir it at 90°C for 7. 5 hours. Cool the purple colored reaction to ambient temperature, quench with ample water and extract the resulting aqueous mixture into dichloromethane. Wash the combined extracts with water and brine; then dry (sodium sulfate) and evaporate them in vacuo. Purify the resulting dark solid on a flash column (silica gel; 0%-5% gradient of EtOAc in CH2C12) to provide 2.00 g of the title compound (86%).
86% With potassium acetate In dimethyl sulfoxide at 90℃; for 7.5h; Inert atmosphere; 8 Intermediate Preparation 8N-tert-Butyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzenesulfonamide Procedure P': A 25 mL DMSO mixture of 4-bromo-N-tert-butyl-benzenesulfonamide (CAS 93281-65-3) (2000 mg, 6.84 mmol), bis(pinacolato)diboron (2090 mg, 8.21 mmol), [1,1 bis(diphenylphosphino)ferrocene]dichloropalladium(II) complex with CH2Cl2 (1:1) (175 mg, 240 mmol), and KOAc (2020 mg, 20.5 mmol) is stirred under N2 at 90° C. for 7.5 hours. Reaction mixture is allowed to cool, is diluted with H2O and is extracted with CH2Cl2. The CH2Cl2 extract is washed with H2O and brine, dried (Na2SO4) and evaporated. The crude product is purified by silica-gel column chromatography (gradient: 100% CH2Cl2 to 5% EtOAc/CH2Cl2) give the intermediate N-tert-butyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzenesulfonamide (2000 mg, 86% yield). (MS (ES-) 256 (boronic acid).
68% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 95℃; for 2h; Inert atmosphere;
60% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 80℃; for 16h; Inert atmosphere; 17 Preparation of Compound 17-b Under nitrogen, to a suspension of compound 17-c (500 mg, 1.72 mmol), bis(pinacolato)diboron (524 mg, 2.06 mmol) and potassium acetate (505 mg, 5.15 mmol) in 1,4-dioxane (5 mL) was added Pd(dppf)Cl2 (130 mg, 0.17 mmol). The mixture was stirred at 80° C. for 16 hours. After concentration of the mixture under reduced pressure, the residue was diluted with water (50 mL), then extracted with ethyl acetate (50 mL×3). The organic layers were combined and washed with water (50 mL×3) and saturated brine (50 mL) in sequence. After dried over anhydrous sodium sulfate, the mixture was filtrated, the filtrate was concentrated under reduced pressure. The residue was purified by silica column chromatography (petroleum ether:ethyl acetate=5:1) to give white solid 17-b (350 mg, yield: 60%). LC-MS (ESI): m/z=340 [M+H]+.

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