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Chemical Structure| 1256360-04-9 Chemical Structure| 1256360-04-9

Structure of 1256360-04-9

Chemical Structure| 1256360-04-9

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Product Details of [ 1256360-04-9 ]

CAS No. :1256360-04-9
Formula : C18H28BNO4
M.W : 333.23
SMILES Code : O=C(OC(C)(C)C)NC1=CC=C(B2OC(C)(C)C(C)(C)O2)C(C)=C1
MDL No. :MFCD16295118
InChI Key :YNSJUGFYOGEXHY-UHFFFAOYSA-N
Pubchem ID :53217224

Safety of [ 1256360-04-9 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of [ 1256360-04-9 ]

* 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 [ 1256360-04-9 ]

[ 1256360-04-9 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 1256360-04-9 ]
  • [ 117635-21-9 ]
  • [ 1362735-95-2 ]
YieldReaction ConditionsOperation in experiment
38% With Aliquat 336; sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In water; toluene; at 90℃; for 42h;Inert atmosphere; In the dry box the mixture of boronic acid pinacol ester,3, (5.6g, 16.82mmol), 1 ,4-dibromo-2,5-dihexylbenzene (3.4g, 8.4mmol), Aliquat 336 (0.8g), and Pd(PPh3) (0.486g, 0.421 mmol) in degassed toluene (100ml_) was prepared. Outside dry box, the degassed Na2CO3 (2.67g, 25.23mmol in 50 ml_ of water) solution was added to the former mixture under nitrogen, and then the resultant mixture was stirred at 90C for 42hrs. The organic layer was separated and the aqueous layer was extracted with ethyl acetate. The combined organic layers were dried over anhydrous MgSO4. Filtration, concentration of the filtrate, and then the silica column chromatography (0-3% ethyl acetate in hexane) provided the desired product (2.1 1 g, 38% yield) as a viscous liquid. This diboc-protected material was deprotected by the overnight reaction at room temperature with TFA solution (5ml_ of TFA in 50ml_ of DCM). The reaction mixture was concentrated under reduced pressure followed by the neutralization with saturated NaHCO3. Ethyl acetate extraction, drying over anhydrous MgSO4, concentration of the organic layer under reduced pressure, then silica column chromatography (30% ethyl acetate in hexane) provided the desired diamine material,7, (1 .16g, 80% yield) as a viscous liquid.
38% With tetrakis(triphenylphosphine) palladium(0); Aliquat 336; sodium carbonate; In toluene; at 90℃; for 42h;Inert atmosphere; Step 3: In the dry box the mixture of boronic acid pinacol ester,3, (5.8g.16.B2mmol), 1,4-dlbmmo-295-dthexylbenzene(3.4g, 8.4mmol), .Aiiquat 336(0.Bg), and Pd(PP%)4 (0.486g, 0421 mmol) in degassed toluene (lOOmL) was prepared. Outside dry box, the degassed Na2003 (2.87g, 2523mmo1 In 50 mL of water) solution was added to the fomier mixture under nitrogen, and then the resultant mixture was stirred at 90C for 42hrs. Theorganic layer was separated and the aqueous layer was extracted with ethyl acetate. The combined orgqnlc layers were dried over anhydrous MgSO4. Filtration, concentration & the filtrate, and then the silica column chromatography (0-3% ethyl acetae in hexane) provided the desired product (2Mg, 8% yield) as a viscous liquid
38% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In water; toluene; at 90℃; for 42h;Inert atmosphere; Glovebox; In the dry box the mixture of boronic acid pinacol ester,3, (5.6 g, 16.82 mmol), <strong>[117635-21-9]1,4-dibromo-2,5-dihexylbenzene</strong> (3.4 g, 8.4 mmol), Aliquat 336 (0.8 g), and Pd(PPh3)4 (0.486 g, 0.421 mmol) in degassed toluene (100 mL) was prepared. Outside dry box, the degassed Na2CO3 (2.67 g, 25.23 mmol in 50 mL of water) solution was added to the former mixture under nitrogen, and then the resultant mixture was stirred at 90 C. for 42 hrs. The organic layer was separated and the aqueous layer was extracted with ethyl acetate. The combined organic layers were dried over anhydrous MgSO4. Filtration, concentration of the filtrate, and then the silica column chromatography (0-3% ethyl acetae in hexane) provided the desired product (2.11 g, 38% yield) as a viscous liquid. This diboc-protected material was deprotected by the overnight reaction at room temperature with TFA solution (5 mL of TFA in 50 mL of DCM). Concentration of the reaction mixture followed by the neutralization with saturated NaHCO3, then silica column chromatography (30% ethylacetae in hexane) provided the desired diamine material,7, (1.16 g, 80% yield) as a viscous liquid.
 

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