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Chemical Structure| 191170-76-0 Chemical Structure| 191170-76-0

Structure of 191170-76-0

Chemical Structure| 191170-76-0

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Product Details of [ 191170-76-0 ]

CAS No. :191170-76-0
Formula : C16H16BrNO2
M.W : 334.21
SMILES Code : O=C(OCC1=CC=CC=C1)NCCC2=CC=C(Br)C=C2
MDL No. :MFCD11616722
InChI Key :WIUKEHNGQSSRHQ-UHFFFAOYSA-N
Pubchem ID :12030670

Safety of [ 191170-76-0 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302
Precautionary Statements:P280-P305+P351+P338

Application In Synthesis of [ 191170-76-0 ]

* 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 [ 191170-76-0 ]

[ 191170-76-0 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 850568-54-6 ]
  • [ 191170-76-0 ]
  • [ 1146546-95-3 ]
YieldReaction ConditionsOperation in experiment
77% With sodium carbonate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In water; N,N-dimethyl-formamide; at 85℃; for 18.1667h; To a solution of the bromide obtained above (5.5 g, 16.5 mmol) and the boronic acid 1.2 (7.3 g, 33 mmol) in 50 mL of DMF is added an aq. Na2CO3 solution (2 M, 22 niL, 44 mmol). The mixture is purged with Ar2 for 10 min. PdCl2(dppf) (672 mg, 0.82 mmol) is then added. The reaction is stirred under Ar2 at 85°C for 18 h. After cooling the reaction mixture is poured into water (200 mL). The mixture then is extracted with EtOAc (50 mLx 3). The organic layer is separated and dried over Na2SO4 and concentrated in vacuo. The crude product is purified by chromatography to provide the desired product 1.3 (5.5 g, 77percent).
  • 2
  • [ 191170-76-0 ]
  • [ 392338-15-7 ]
  • tert-butyl (R)-(1-(4-(2-aminoethyl)phenyl)pyrrolidin-3-yl)(methyl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With palladium diacetate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; sodium t-butanolate; In toluene; at 100℃;Inert atmosphere; (1200) [00398] Into a 250-mL round-bottom flask, purged and maintained under an inert atmosphere of nitrogen, was added benzyl N-[2-(4-bromophenyl)ethyl]carbamate (2.00 g, 5.98 mmol), tert- butyl jV-methyl-A-[(3R)-pyrrolidin-3-yl]carbamate (1.30 g, 6,49 mmol), toluene (20 mL), Pd(OAc)2 (0.135 g, 0.600 mmol), XantPhos (0.347 g, 0.600 mmol), and NaOtBu (1.70 g, 17.69 mmol). The reaction mixture was stirred overnight at 100 C in an oil bath and then cooled and concentrated in vacuo to provide a crude product that was purified via silica gel chromatography and eluted with dichloromethane/methanoi (10: 1) to afford feT/-butyl (R)-(l-(4-(2- aminoethyl)phenyi)pyrrolidin-3-yl)(methyl)carbamate as yellow oil ( 1.0 g, 52 %). LCMS (ESI, m/z): 320 M l | .
  • 3
  • [ 454482-11-2 ]
  • [ 191170-76-0 ]
  • benzyl (4-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)phenethyl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
77% With potassium phosphate; chloro(2-dicyclohexylphosphino-2?,4?,6?-triisopropyl-1,1?-biphenyl)[2-(2?-amino-1,1?-biphenyl?)]palladium(II); In 1,4-dioxane; water; at 90℃;Inert atmosphere; (1392) [00447] To a one dram vial was added benzyl 4-bromophenethylcarbamate (1.50 g, 4.49 mmol), l-methyl-4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-l,2,3,6-tetrahydropyridine (1.00 g, 4.49 mmol), potassium phosphate tribasic (3.8 1 g, 18.0 mmol), and XPhos 2nd generation Pd precatalyst (0.353 g, 0.449 mmol). The flask was backfilled with dry nitrogen 3 times and degassed dioxane (9.8 ml) and water (2,80 ml) were added. The reaction mixture was heated to 90 °C overnight and then cooled to RT, filtered through a bed of Celite, and concentrated m vacuo. The resulting crude product was purified by FCC eluting with 20 - 30percent EtOAc in hexanes to afford benzyl (4-(l-methyl-l,2,3,6-tetrahydropyridin-4- yl)phenethyl)carbamate as a white solid (1.2 g, 77percent). I CMS (ESI, m/z): 351 | \ H j
 

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