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Chemical Structure| 1290039-85-8 Chemical Structure| 1290039-85-8

Structure of 1290039-85-8

Chemical Structure| 1290039-85-8

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Product Details of [ 1290039-85-8 ]

CAS No. :1290039-85-8
Formula : C24H17NO
M.W : 335.40
SMILES Code : O1C=2C=CC=CC2C=3C=CC(=CC13)NC=4C=CC(=CC4)C=5C=CC=CC5
MDL No. :N/A
InChI Key :SZOFSHPSDMYXKP-UHFFFAOYSA-N
Pubchem ID :68282013

Safety of [ 1290039-85-8 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319
Precautionary Statements:P501-P270-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330

Application In Synthesis of [ 1290039-85-8 ]

* 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 [ 1290039-85-8 ]

[ 1290039-85-8 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 26608-06-0 ]
  • [ 92-67-1 ]
  • [ 1290039-85-8 ]
YieldReaction ConditionsOperation in experiment
95% With tri-tert-butyl phosphine; palladium diacetate; sodium t-butanolate; In toluene; at 120℃; for 12h;Inert atmosphere; SM1 (3.0 g, 20 mmol), SM2 (5.0 g, 20 mmol), Pd(OAc)2 (0.45 g, 2 mmol), P(t-13u)3 (0.81 g, 4 mmol), and NaOtl3u (7.7 g, 80 mmol) were dissolved into toluene 200 ml in a 500 ml round bottom flask under a nitrogen atmosphere to form a mixture. Then, the mixture was heated and stirred while being refluxed for 12 hours. An organic layer was extracted with chloroform and washed with water. Water was removed from the organic layer with anhydrous magnesium sulfate and the organic layer was filtered. Then, an organic solvent was distilled away under a reduced pressure and removed from the organic layer and then was subjected to column purification, to obtain Compound 72-1 (6.4 g, yield:95%).
87% With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; potassium tert-butylate; In toluene; at 85℃; for 4h; Synthesis of Intermediate D-3 5.08 g (30 mmol) of [1,1'-biphenyl]-4-amine, 4.94 g (20.0 mmol) of <strong>[26608-06-0]3-bromodibenzo[b,d]furan</strong>, 0.37 g (0.4 mmol) of Pd2(dba)3, 0.08 g (0.4 mmol) of P(tBu)3, and 5.76 g (60 mmol) of KOtBu were dissolved in 150 mL of toluene, and then, the resulting mixed solution was stirred at a temperature of 85 C. for 4 hours. After the obtained reaction solution was cooled to room temperature, an extraction process was performed thereon three times using 50 mL of water and 50 mL of diethylether. An organic layer obtained from the resulting solution was dried using magnesium sulfate, and a solvent was removed therefrom by evaporation. The residue obtained therefrom was separation-purified by silica gel column chromatography, thereby completing the preparation of 5.84 g (yield: 87%) of Intermediate D-3. The prepared compound was identified by LC-MS. (C24H17NO: M+ 335.41)
87% With tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate; XPhos; In toluene; at 108℃; for 4h;Inert atmosphere; <strong>[26608-06-0]3-bromodibenzofuran</strong> (10.0 g, 40.5 mmol), 4-aminobiphenyl (7.53 g, 44.5 mmol),Tris(dibenzylideneacetone)dipalladium (0.37 g, 0.40 mmol), 2-dicyclohexylphosphino-2,4,6-triisopropylbiphenyl (0.39 g, 0.81 mmol)And sodium tert-butoxide (5.83 g, 60.7 mmol) was added to toluene (80 mL), heated to 108 C under nitrogen, stirring for 4 h;After cooling to room temperature, the reaction solution was washed with water and dried over magnesium sulfate.After filtration, the filtrate was evaporated under reduced pressure; the crude product was recrystallized and purified using ethyl acetate/n-heptane.The light gray solid intermediate II-C (11.8 g, 87%) was obtained.
86% With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate; In toluene; at 100℃; for 5h;Inert atmosphere; 16.9 g (100 mmol, 1.0 eq.) p-phenylanilineAnd 29.7 g of <strong>[26608-06-0]3-bromodibenzofuran</strong> (120 mmol, 1.2 eq.) was placed in a dry 2 L three-necked flask.Then add 900 ml of toluene which has been dried and degassed as a solvent.Nitrogen gas was passed for 15 minutes. An additional 19.2 g (200 mmol, 2.0 eq.) of sodium tert-butoxide was added.1.8 g (2% mol) of a catalyst Pd2(dba)3 and 8.1 ml (4% mol) of a solution of P(t-bu)3 in toluene (m/v, 10%). The temperature was raised to 100 C and the reaction was carried out for 5 hours. When the reaction is over,Cool to room temperature, add activated carbon adsorption, suction filtration, and remove the solvent by rotary evaporation.Recrystallized from toluene and ethanol,28.8 g of intermediate I were obtained,The yield was 86%.
83% (3) Synthesis of Intermediate-18
77% With tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate; XPhos; In toluene; at 105 - 110℃; for 1h;Inert atmosphere; <strong>[26608-06-0]3-bromodibenzofuran</strong> (10.0 g, 40.5 mmol),4-aminobiphenyl (7.5 g, 44.5 mmol),Tris(dibenzylideneacetone)dipalladium (0.4 g, 0.4 mmol),2-Dicyclohexylphosphino-2,4,6-triisopropylbiphenyl (0.4 g, 0.8 mmol) and sodium tert-butoxide (5.8 g, 60.7 mmol) were added to toluene (100 mL).Heated to 105-110 C under nitrogen protection,After stirring for 1 hour; cooling to room temperature, the reaction solution was washed twice with water, dried over magnesium sulfate, filtered, and then filtered, and the filtrate was passed through a silica gel column, and the solvent was evaporated under reduced pressure; Solid intermediate VI-B (10.4 g, 77%).
76% With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate; In toluene; at 100℃; for 3h;Inert atmosphere; 22 g (120 mmol, 1.2 eq.) was added to a dry 2L three-necked flaskIntermediate HAnd 24.7g3-Bromobenzodifuran(100mmol, 1.0eq.),Then, dried and degassed 900 ml of toluene was added as a solvent and nitrogen was passed for 15 minutes.Then add 19.2 g (200 mmol, 2.0 eq.) sodium tert-butoxide,1.8 g (2% mol) of catalyst Pd2(dba)3 and 8.1 ml (4% mol) P(t-bu)3The toluene solution (m/v, 10%).Warm up to 100C,The reaction was allowed to proceed overnight for 3 hours.After the reaction is over,Cool to room temperatureAdd activated carbon adsorption,Suction filtrationSpin off the solvent,Recrystallization from toluene and ethanol,25.5 g of Intermediate I are obtained,The yield is 76%.
70.7% With tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate; In toluene; at 100℃; for 3h; Toluene (300 mL) was added to <strong>[26608-06-0]3-bromo-dibenzofuran</strong> (20g, 0.081mol, TCI), 4- aminobiphenyl (16.44g, 0.097mol, sigma aldrich), sodium tert-butoxide (15.56g, 0.16mol, Sigma Aldrich), a mixture of Pd (dba) 2 (2.33g, 0.004mol, sigma aldrich) and tri-tert-butylphosphine (1.64g, 0.008mol, sigmaaldrich) in, and stirred at for 3 hours at 100 . After completion of the reaction, and the mixture was extracted by column to give compound 18-1 (19.2g, yield: 70.7%).
57% With tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate; XPhos; In toluene; at 108℃; for 1h;Inert atmosphere; Combine <strong>[26608-06-0]3-bromodibenzofuran</strong> (4g, 16.19mmol), 4-aminobiphenyl (2.79g, 16.51mmol), tris (dibenzylideneacetone) dipalladium (0.15g, 0.16mmol), 2-bicyclo Hexylphospho-2 ', 4', 6'-triisopropylbiphenyl (0.15g, 0.32mmol) and sodium tert-butoxide (2.33g, 24.28mmol) were added to toluene (40mL) and heated to 108 under nitrogen protection , stirring for 1h; after the reaction liquid was cooled to room temperature, the reaction liquid was washed with water until neutral, and then magnesium sulfate was added to the organic phase for drying, and the filtrate was filtered to remove the solvent under reduced pressure; dichloromethane / n-heptane (v / v ) = 1: 5 is purified by silica gel column chromatography for the crude mobile solid, to obtain solid intermediate II-D (3.1 g, yield 57%).

 

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