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[ CAS No. 4885-19-2 ] {[proInfo.proName]}

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Chemical Structure| 4885-19-2
Chemical Structure| 4885-19-2
Structure of 4885-19-2 * Storage: {[proInfo.prStorage]}
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Product Details of [ 4885-19-2 ]

CAS No. :4885-19-2 MDL No. :MFCD08276024
Formula : C11H16BrN Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 242.16 Pubchem ID :-
Synonyms :

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Application In Synthesis of [ 4885-19-2 ]

* 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 [ 4885-19-2 ]

[ 4885-19-2 ] Synthesis Path-Downstream   1~6

  • 1
  • [ 5892-99-9 ]
  • [ 4885-19-2 ]
YieldReaction ConditionsOperation in experiment
99% With triethyl borane; phenylsilane; sodium hydroxide In tetrahydrofuran; tert-butyl methyl ether at 20℃; Inert atmosphere; Schlenk technique; Sealed tube; chemoselective reaction;
99% With triethyl borane; phenylsilane; sodium hydroxide In tetrahydrofuran; tert-butyl methyl ether at 80℃; for 48h; Inert atmosphere; Schlenk technique; Glovebox; Sealed tube;
85% With diphenylsilane In tetrahydrofuran for 20h;
  • 2
  • [ 109-89-7 ]
  • [ 589-15-1 ]
  • [ 4885-19-2 ]
YieldReaction ConditionsOperation in experiment
97% for 1h; Heating;
96.6% With potassium carbonate In acetonitrile at 20℃; for 2h; 5.a a) Preparation of N- (4- bromobenzyl) -N- diethylamine (III) The mixture of p-bromobenzylbromide (0.6 g, 2.4 mmol) and potassium carbonate (1.0 g, 7.2 mmol) were dissolved in 15 mL of acetonitrile, diethylamine (0.99 mL, 9.6mmol) was dropped within two minutes slowly into the mixed system, stirred for two hours at room temperature, then the mixture was concentrated under vacuum, water (15 mL) was added to dissolve, and extracted with ethyl acetate (15 mL × 3). The organic layers were combined, washed with brine, dryed with anhydrous sodium sulfate, and concentrated in vacuum to obtain 0.56 g product, yield 96.6%.
96% With potassium carbonate In tetrahydrofuran at 20℃; Inert atmosphere;
88% With triethylamine In tetrahydrofuran at 20℃; for 16h; A mixture of 4-bromobenzyl bromide (1.0 g, 4.0 mmol), triethylamine (0.84 mL,6.0 mmol) and diethylamine (0.84 mL, 8.0 mmol) in THF (20 mL) was stirred at ambient temperature for 16 h. The solvent was evaporated and the resultant residue diluted with saturated aqueous sodium bicarbonate solution and extracted with ethyl acetate (2 x 50 mL). The combined organic layer was dried over sodium sulfate, filtered and evaporated to afford the title compound (0.85 g, 88%). 1H NMR (CDCl3, 300MHz): 7.45-7.38 (m, 2H), 7.27-7.18 (m, 2H), 3.50 (s, 2H), 2.50 (q, J = 7.1Hz, 4H), 1.03 (t, J = 7.1Hz, 6H). LCMS (Method G): RT= 1.98 min, M-H+ = 242.
84.7% With potassium carbonate In acetonitrile at 20℃; for 2h; 1 4.2.2.1 N-(4-(6-bromoquinolin-4-yl)benzyl)-N-ethylethanamine (12a) To a stirred solution of 10 (1.00g, 4.00mmol) and K2CO3 (1.66g, 12.00mmol) in acetonitrile (20mL) was added dropwise diethylamine solution (1.20g, 16.00mmol) at room temperature for 2h. The solvent was evaporated in vacuo and the residue was then dissolved in EtOAc (50mL) and washed with water (20mL×3), the organic layers were washed with brine, and dried over anhydrous Na2SO4. The solvent was evaporated under reduced pressure to provide the 11a (0.83g, 84.7% yield) as an off-white liquid. (0041) Then, a mixture of 11a (0.83g, 3.43mmol), bis(pinacolato)diboron (0.96g, 3.77mmol), PdCl2(dppf)-CH2Cl2 (0.084g, 0.103mmol) and potassium acetate (0.67g, 6.86mmol) in anhydrous 1,4-dioxane (15mL) was purged with argon and heated at 100°C for 2.5h. The reaction was then treated with 6 (1.20g, 3.60mmol), 2.0M aqueous Na2CO3 (5mL) and another portion of PdCl2(dppf)-CH2Cl2 (0.084g, 0.103mmol), then heated at 110°C for 12h under argon. The reaction mixture was cooled to room temperature, filtered, and concentrated. The final compound was purified by MPLC (ISCO CombiFlash purification system) (MeOH/DCM, eluted from 0% to 10%), The fractions were collected, concentrated to afford 12a (0.72g, 57.2% yield).
74% With potassium carbonate In tetrahydrofuran; water for 12h; Reflux; 16 Into a 500 ml round-bottomed flask were added 150 ml THF, 5 ml water, 2.2 g potassium carbonate, 6 ml diethyl amine, and 5 g p-bromobenzyl bromide. The resultant mixture was refluxed for 12 h. The mixture was then cooled to room temperature, into which 6 ml concentrated HCl was added, followed by the addition of 150 ml water. The mixture was extracted with 100 ml diethyl ether for three times. The diethyl ether solution was dried with anhydrous magnesium sulfate over night and then the magnesium sulfate was removed by filtration. Diethyl ether was evaporated and the raw product was purified by a silica gel column using hexane/chloroform mixture (1:1 by volume) as the eluent. (p-bromobenzyl)diethyl amine (BBDA) was obtained in 74% yield (3.6 g). Characterization data of BBDA: 1H NMR (CDCl3, 300 MHz) δ (ppm): 7.40 (d, 2H), 7.23 (d, 2H), 3.51 (5.2H), 2.50 (m, 4H), 1.04 (m, 6H).
With potassium carbonate In tetrahydrofuran at 50℃; for 8h;

  • 3
  • 4-methyl-2-(methylthio)[1,3]oxazolo[4,5-b]pyridin-4-ium tosylate [ No CAS ]
  • [ 29786-93-4 ]
  • [ 2584-47-6 ]
  • [ 4885-19-2 ]
  • [ 305801-81-4 ]
YieldReaction ConditionsOperation in experiment
Stage #1: n-butyllithium; 1,4-dimethylquinolin-2(1H)-one; 1-(4-bromophenyl)-N,N-diethylmethanamine In tetrahydrofuran at -78℃; for 1h; Stage #2: With acetic acid In tetrahydrofuran at -78 - 20℃; for 1h; Stage #3: 4-methyl-2-(methylthio)[1,3]oxazolo[4,5-b]pyridin-4-ium tosylate With sodium hydroxide; triethylamine; sodium iodide more than 3 stages; 9 Example 9; Preparation of Compound 22 To 0.605 g of 4'-bromobenzyldiethylamine in 10 mL of THF at -78° C. under nitrogen is added 0.8 mL of a 2.5 M butyl lithium in THF, followed by a solution of 0.173 g of 1,4-dimethyl-2-quinolone in 10 mL of THF. After one hour at -78° C., 1 mL of acetic acid is added. After warming to room temperature for another hour the volatiles are evaporated and the residue is dissolved in 10 mL CH2Cl2. To this solution is added 0.67 g of Compound 2, followed by 1 mL triethylamine. After one hour at room temperature the volatiles are evaporated and the residue is dissolved in 7 mL of methanol. This solution is added to a solution of 2.25 g NaI and 0.8 g NaOH in 50 mL water. Compound 22 is filtered, dried and recrystallized from a mixture of DMF and ethyl acetate.
  • 4
  • [ 28240-69-9 ]
  • [ 4885-19-2 ]
  • [ 1329705-04-5 ]
YieldReaction ConditionsOperation in experiment
60% Stage #1: 1-(4-bromophenyl)-N,N-diethylmethanamine With n-butyllithium In tetrahydrofuran; hexane at -45℃; for 0.5h; Inert atmosphere; Stage #2: 1,2-bis(dichlorophosphino)ethane In tetrahydrofuran; hexane at -65℃; for 0.5h; Inert atmosphere;
  • 5
  • [ 927801-23-8 ]
  • [ 4885-19-2 ]
  • N-(4-(6-bromoquinolin-4-yl)benzyl)-N-ethylethanamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
42.35% N- (4- bromobenzyl) -N- diethylamine (0.56 g, 2.31 mmol) was dissolved in dioxane (15 mL), bis (pinacolato) diboron was added (0.647g, 2.55 mmol), potassium acetate (0.452 g, 4.62 mmol) and palladium catalyst PdCl2 (dppf) CH2Cl2 (0.057 g, 0.069 mmol) were added, heated and refluxed for 3h at 110C under nitrogen protected condition, the reaction was stopped after detected that the raw material point had disappeared. 6-bromo-4-iodo quinoline (0.694g, 2.079mmol) and another part of palladium catalyst PdCl2 (dppf) CH2Cl2 (0.057 g, 0.069 mmol) and a solution of 1M K2CO3 (5.00 mL) were added to the mixed system, heated and refluxed for 10h at 110C under nitrogen protected condition and then the reaction was stopped. The solvent was evaporated to dry, and water (50 mL) was added, and extracted with dichloromethane (4 × 15 mL), the organic layers were combined, washed with brine (15 mL), dried with anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, purified by silica gel column chromatography (eluent: dichloromethane / methanol = 20: 1) to obtain 0.36 g product, yield 42.35%. MS(ESI)m/z : 369.71 (M + H+, 79Br), 371.71 (M + H+, 81Br).
  • 6
  • [ 4885-19-2 ]
  • [ 73183-34-3 ]
  • [ 1012785-44-2 ]
YieldReaction ConditionsOperation in experiment
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In 1,4-dioxane at 100℃; for 2.5h; Inert atmosphere; 4.2.2.1 N-(4-(6-bromoquinolin-4-yl)benzyl)-N-ethylethanamine (12a) To a stirred solution of 10 (1.00g, 4.00mmol) and K2CO3 (1.66g, 12.00mmol) in acetonitrile (20mL) was added dropwise diethylamine solution (1.20g, 16.00mmol) at room temperature for 2h. The solvent was evaporated in vacuo and the residue was then dissolved in EtOAc (50mL) and washed with water (20mL×3), the organic layers were washed with brine, and dried over anhydrous Na2SO4. The solvent was evaporated under reduced pressure to provide the 11a (0.83g, 84.7% yield) as an off-white liquid. (0041) Then, a mixture of 11a (0.83g, 3.43mmol), bis(pinacolato)diboron (0.96g, 3.77mmol), PdCl2(dppf)-CH2Cl2 (0.084g, 0.103mmol) and potassium acetate (0.67g, 6.86mmol) in anhydrous 1,4-dioxane (15mL) was purged with argon and heated at 100°C for 2.5h. The reaction was then treated with 6 (1.20g, 3.60mmol), 2.0M aqueous Na2CO3 (5mL) and another portion of PdCl2(dppf)-CH2Cl2 (0.084g, 0.103mmol), then heated at 110°C for 12h under argon. The reaction mixture was cooled to room temperature, filtered, and concentrated. The final compound was purified by MPLC (ISCO CombiFlash purification system) (MeOH/DCM, eluted from 0% to 10%), The fractions were collected, concentrated to afford 12a (0.72g, 57.2% yield).
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