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[ CAS No. 178396-31-1 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 178396-31-1
Chemical Structure| 178396-31-1
Chemical Structure| 178396-31-1
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Product Details of [ 178396-31-1 ]

CAS No. :178396-31-1 MDL No. :MFCD11847622
Formula : C10H8BrN Boiling Point : -
Linear Structure Formula :- InChI Key :RYYKJLRAFMKRSC-UHFFFAOYSA-N
M.W : 222.08 Pubchem ID :22403410
Synonyms :

Safety of [ 178396-31-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 178396-31-1 ]

* 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 [ 178396-31-1 ]

[ 178396-31-1 ] Synthesis Path-Downstream   1~50

  • 1
  • [ 178396-31-1 ]
  • [ 75908-52-0 ]
YieldReaction ConditionsOperation in experiment
With sulfuric acid; nitric acid
  • 2
  • [ 56-81-5 ]
  • [ 583-75-5 ]
  • [ 178396-31-1 ]
YieldReaction ConditionsOperation in experiment
92% Stage #1: glycerol; 4-Bromo-2-methylaniline With sulfuric acid; sodium iodide In water at 140℃; for 3h; Stage #2: Stage #3: With sodium hydroxide In water 11 6-bromo-8-methylquinoline. Glycerol (2.3 ml, 32.2 mmol) was added dropwise via syringe to a solution of 4-bromo-2-methylaniline (5.00 g, 26.8 mmol) and sodium iodide (52 mg, 0.349 mmol) in 75% aq H2SO4 (15.81 ml, 120 mmol) at 140° C. The mixture was held at this temperature for 3 hours. The reaction mixture was neutralized to a pH of 7 with aq NaOH. This mixture was extracted with EtOAc and the combined organics were washed with brine, dried over MgSO4 and concentrated. Column chromatography on silica gel (5-25% EtOAc in hexanes) afforded intermediate 11 (5.50 g, 24.7 mmol, 92%). 1H NMR (400 MHz, CDCl3) δ ppm 8.93 (dd, J=4.28, 1.76 Hz, 1H), 8.03 (dd, J=8.31, 1.76 Hz, 1H), 7.82 (d, J=2.01 Hz, 1H), 7.65 (d, J=1.01 Hz, 1H), 7.40 (dd, J=8.18, 4.15 Hz, 1H), 2.78 (s, 3H). Mass 221 [M+H]+.
With sulfuric acid; 2-hydroxynitrobenzene at 160 - 180℃;
With sulfuric acid; sodium iodide In water at 140 - 145℃; for 4h; Inert atmosphere; Schlenk technique;
With sulfuric acid; sodium iodide In water at 140 - 145℃; for 4h; Schlenk technique;
With sulfuric acid; sodium iodide In water at 140 - 145℃; for 2.5h; Inert atmosphere; Schlenk technique;
With sulfuric acid; sodium iodide at 140℃; for 6h;
With sulfuric acid; sodium iodide at 140℃; for 6h;
With sulfuric acid; sodium iodide In water at 140 - 145℃; for 6h;

  • 3
  • [ 178396-31-1 ]
  • [ 99455-14-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 125 °C / Erwaermen einer wss .Loesung des Reaktionsprodukts mit Kalium-hexacyanoferrat(III) und wss. Kalilauge 2: phosphoryl chloride / -14 °C / und Erhitzen des Rktgem. mit Phosphor(V)-chlorid
  • 4
  • [ 178396-31-1 ]
  • [ 99465-08-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 125 °C / Erwaermen einer wss .Loesung des Reaktionsprodukts mit Kalium-hexacyanoferrat(III) und wss. Kalilauge 2: phosphoryl chloride / -14 °C / und Erhitzen des Rktgem. mit Phosphor(V)-chlorid 3: water; sulfuric acid / 180 °C
  • 5
  • [ 178396-31-1 ]
  • [ 50358-36-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: nitric acid; sulfuric acid 2: Raney nickel; acetone / Hydrogenation
  • 6
  • [ 178396-31-1 ]
  • <i>N</i>-(6-bromo-8-methyl-[5]quinolyl)-acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: nitric acid; sulfuric acid 2: Raney nickel; acetone / Hydrogenation 3: acetic acid
  • 7
  • [ 178396-31-1 ]
  • [ 858467-33-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 125 °C / Erwaermen einer wss .Loesung des Reaktionsprodukts mit Kalium-hexacyanoferrat(III) und wss. Kalilauge 2: phosphoryl chloride / -14 °C / und Erhitzen des Rktgem. mit Phosphor(V)-chlorid 3: nitric acid; sulfuric acid 4: Raney nickel; acetone / Hydrogenation
  • 8
  • [ 178396-31-1 ]
  • [ 854834-69-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 125 °C / Erwaermen einer wss .Loesung des Reaktionsprodukts mit Kalium-hexacyanoferrat(III) und wss. Kalilauge 2: phosphoryl chloride / -14 °C / und Erhitzen des Rktgem. mit Phosphor(V)-chlorid 3: nitric acid; sulfuric acid 4: water; sulfuric acid 5: Raney nickel; ethanol / 80 °C / 14710.2 Torr / Hydrogenation
  • 9
  • [ 178396-31-1 ]
  • 6-bromo-2-chloro-8-methyl-5-nitro-quinoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 125 °C / Erwaermen einer wss .Loesung des Reaktionsprodukts mit Kalium-hexacyanoferrat(III) und wss. Kalilauge 2: phosphoryl chloride / -14 °C / und Erhitzen des Rktgem. mit Phosphor(V)-chlorid 3: nitric acid; sulfuric acid
  • 10
  • [ 178396-31-1 ]
  • [ 854834-59-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 125 °C / Erwaermen einer wss .Loesung des Reaktionsprodukts mit Kalium-hexacyanoferrat(III) und wss. Kalilauge 2: phosphoryl chloride / -14 °C / und Erhitzen des Rktgem. mit Phosphor(V)-chlorid 3: nitric acid; sulfuric acid 4: water; sulfuric acid
  • 11
  • [ 178396-31-1 ]
  • <i>N</i>-(6-bromo-2-hydroxy-8-methyl-[5]quinolyl)-acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: 125 °C / Erwaermen einer wss .Loesung des Reaktionsprodukts mit Kalium-hexacyanoferrat(III) und wss. Kalilauge 2: phosphoryl chloride / -14 °C / und Erhitzen des Rktgem. mit Phosphor(V)-chlorid 3: nitric acid; sulfuric acid 4: water; sulfuric acid 5: Raney nickel; ethanol / 80 °C / 14710.2 Torr / Hydrogenation
  • 12
  • [ 178396-31-1 ]
  • <i>N</i>-(6-bromo-2-chloro-8-methyl-[5]quinolyl)-acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 125 °C / Erwaermen einer wss .Loesung des Reaktionsprodukts mit Kalium-hexacyanoferrat(III) und wss. Kalilauge 2: phosphoryl chloride / -14 °C / und Erhitzen des Rktgem. mit Phosphor(V)-chlorid 3: nitric acid; sulfuric acid 4: Raney nickel; acetone / Hydrogenation 5: acetic acid
  • 13
  • [ 178396-31-1 ]
  • <i>N</i>-(6-bromo-8-methyl-[5]quinolyl)-benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: nitric acid; sulfuric acid 2: Raney nickel; acetone / Hydrogenation 3: aqueous NaOH
  • 14
  • [ 178396-31-1 ]
  • [ 926207-02-5 ]
YieldReaction ConditionsOperation in experiment
77% With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In tetrachloromethane Heating / reflux; 12 6-bromo-8-(bromomethyl)quinoline. To a solution of 6-bromo-8-methylquinoline (2.00 g, 9.00 mmol) in CCl4 (80 ml) was added NBS (1.76 g, 9.90 mmol) and AIBN (118 mg, 0.72 mmol). The mixture was refluxed overnight under N2 then cooled, diluted with DCM and quenched with 10% NaHSO3. The layers were separated and the organic layer was washed with sat NaHCO3 and brine then dried over MgSO4 and concentrated. Column chromatography on silica gel (5-25% EtOAc in hexanes) afforded intermediate 12 (2.10 g, 6.97 mmol, 77%). 1H NMR (400 MHz, CDCl3) δ ppm 8.99 (dd, J=4.28, 1.76 Hz, 1H), 8.07 (dd, J=8.31, 1.51 Hz, 1H), 7.93 (dd, J=14.98, 2.14 Hz, 2H), 7.46 (dd, J=8.31, 4.03 Hz, 1H), 5.16 (s, 2H). Mass 299 [M+H]+.
  • 15
  • [ 557-21-1 ]
  • [ 178396-31-1 ]
  • [ 1100207-54-2 ]
YieldReaction ConditionsOperation in experiment
92% In water; N,N-dimethyl-formamide at 120℃; 32 8-methylquinoline-6-carbonitrile. A solution of 6-bromo-8-methylquinoline (500 mg, 2.251 mmol) in DMF (8 ml) and water (160 μl) was degassed by bubbling through N2 for 5 minutes. Then 1,1'-bis(diphenyphosphino)ferrocene (250 mg, 0.450 mmol) and Pd2 dba3 (206 mg, 0.225 mmol) were added followed by zinc cyanide (0.143 ml, 2.251 mmol). The mixture was heated at 120° C. overnight then cooled, filtered through a pad of celite and washed with EtOAc. The filtrate was washed with water and brine, dried over MgSO4, filtered and concentrated. The crude residue was purified by column chromatography on silica gel (5-30%) EtOAc in hexanes to afford intermediate 18 (347 mg, 2.06 mmol, 92%). 1H NMR (500 MHz, CDCl3) δ ppm 8.99-9.11 (m, 1H), 8.16-8.22 (m, 1H), 8.07 (s, 1H), 7.70 (s, 1H), 7.52 (dd, J=8.24, 4.27 Hz, 1H), 2.83 (s, 3H). Mass 169 [M+H]+.
  • 16
  • [ 178396-31-1 ]
  • [ 501-65-5 ]
  • 6-bromo-8-(2,3-diphenylallyl)quinoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; copper(II) acetate monohydrate In N,N-dimethyl-formamide at 80℃; for 24h; Schlenk technique; Inert atmosphere;
  • 17
  • [ 178396-31-1 ]
  • 6-bromo-8-(nitromethyl)quinoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
94% With tert.-butylnitrite; oxygen; palladium diacetate In 1,2-dichloro-ethane at 90℃; for 48h; Schlenk technique;
63% With N-chloro-succinimide; palladium diacetate; silver nitrate In acetonitrile at 90℃; for 30h; 10 0.5 mmol of 6-bromo-8-methylquinoline, 0.05 mmol of palladium diacetate, 1 mmol of N-chlorosuccinimide, 1 mmol of silver nitrite and 5 ml of acetonitrile were successively added to a 25 ml sealed pressure vessel. The mixture was heated in a 90 ° C oil bath30 hours. After the TLC test reaction was complete, the reaction solution was diluted with dichloromethane to give a clear solution which was separated by column chromatography (eluent ratio: petroleum ether to ethyl acetate volume ratio of 10: 1). The solvent was distilled off to give 6-bromo-8-(nitromethyl)quinoline (63% yield).
  • 18
  • [ 178396-31-1 ]
  • [ 133745-75-2 ]
  • N-((6-bromoquinolin-8-yl)methyl)-N-(phenylsulfonyl)benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
53% With copper diacetate; lithium carbonate In 1,2-dichloro-ethane; acetonitrile at 110℃; for 22h; Inert atmosphere;
  • 19
  • [ 1638287-52-1 ]
  • [ 178396-31-1 ]
  • N-((6-bromoquinolin-8-yl)methyl)-4-fluoro-N-((4-nitrophenyl)sulfonyl)benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% With copper diacetate; lithium carbonate In 1,2-dichloro-ethane; acetonitrile at 110℃; for 22h;
  • 20
  • [ 1942-46-7 ]
  • [ 178396-31-1 ]
  • C20H26BrN [ No CAS ]
YieldReaction ConditionsOperation in experiment
82% With carbonyl(pentamethylcyclopentadienyl)cobalt diiodide; 1-Adamantanecarboxylic acid; silver trifluoromethanesulfonate In 2,2,2-trifluoroethanol at 80℃; for 24h; Inert atmosphere; regioselective reaction;
  • 21
  • [ 271-58-9 ]
  • [ 178396-31-1 ]
  • 2-((6-bromoquinolin-8-yl)methylamino)benzaldehyde [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With silver hexafluoroantimonate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; Trimethylacetic acid In 1,2-dichloro-ethane at 80℃; Schlenk technique;
67% With tris(acetonitrile)(η5-pentamethylcyclopentadienyl)rhodium(III) hexafluoroantimonate; Trimethylacetic acid In dichloromethane at 100℃; for 20h; Inert atmosphere;
  • 22
  • [ 1460-08-8 ]
  • [ 178396-31-1 ]
  • 2-((6-bromoquinolin-8-yl)methyl)-3-hydroxycyclohex-2-en-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
97% With tris(acetonitrile)(η5-pentamethylcyclopentadienyl)rhodium(III) hexafluoroantimonate; copper diacetate In 1,2-dichloro-ethane at 55℃; for 3h; regioselective reaction;
  • 23
  • [ 930-88-1 ]
  • [ 178396-31-1 ]
  • 3-((6-bromoquinolin-8-yl)methyl)-1-methylpyrrolidine-2,5-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With carbonyl(pentamethylcyclopentadienyl)cobalt diiodide; 1-Adamantanecarboxylic acid; silver trifluoromethanesulfonate In 2,2,2-trifluoroethanol at 100℃; for 24h; Sealed tube; Inert atmosphere;
79% With C11H16CoI2O; zinc diacetate; silver trifluoromethanesulfonate at 100℃; for 24h; Inert atmosphere; Representative Procedure for 1,4-Addition of C(sp3)-H Bondsto Maleimides General procedure: A mixture of 8-methylquionoline (28.6 mg, 0.2 mmol, 1.0equiv), N-methylmaleimide (44.4 mg, 0.4 mmol, 2.0 equiv),[Cp*Co(CO)I2] (4.8 mg, 0.01 mmol, 5 mol%), AgOTf (7.7 mg, 0.03mmol, 15 mol%), and Zn(OAc)2 (11.0 mg, 0.06 mmol, 30 mol%)in HFIP (1.0 mL) was stirred under argon at 100 °C for 24 h. Aftercooling to room temperature, the solvent was removed underreduced pressure. The contents were subjected to flash chromatography(petrol ether/EtOAc 2:1) to give the product as whitesolid (46.7 mg, 0.184 mmol, 92%).
62% With silver hexafluoroantimonate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; 1-Adamantanecarboxylic acid In 1,2-dichloro-ethane at 70℃; for 24h; Sealed tube;
  • 24
  • [ 1373758-55-4 ]
  • [ 178396-31-1 ]
  • N-((6-bromoquinolin-8-yl)methyl)thiophene-2-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
60% With silver hexafluoroantimonate; ((η5-cyclopentadienyl)cobalt(I2))2; sodium pivalate In 1,2-dichloro-ethane at 100℃; for 12h; Schlenk technique; Inert atmosphere;
  • 25
  • [ 598-32-3 ]
  • [ 178396-31-1 ]
  • 5-(6-bromoquinolin-8-yl)pentan-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; copper(II) acetate monohydrate; acetic acid In water at 100℃; for 20h; Sealed tube; chemoselective reaction;
  • 26
  • [ 178396-31-1 ]
  • [ 107-02-8 ]
  • 4-(6-bromoquinolin-8-yl)butanal [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% With silver hexafluoroantimonate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; silver(I) acetate In 1,2-dichloro-ethane at 20℃; for 12h; Schlenk technique; Inert atmosphere;
  • 27
  • [ 178396-31-1 ]
  • [ 886-38-4 ]
  • (E)-1-(6-bromoquinolin-8-yl)-3,4-diphenylbut-3-en-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; silver(I) triflimide; Trimethylacetic acid In chlorobenzene; toluene at 90℃; for 24h; Molecular sieve; Inert atmosphere; Sealed tube;
  • 28
  • [ 5256-74-6 ]
  • [ 178396-31-1 ]
  • diethyl 2-((6-bromoquinolin-8-yl)methyl)malonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
53% With silver hexafluoroantimonate; carbonyl(pentamethylcyclopentadienyl)cobalt diiodide; manganese(II) acetate In dichloromethane at 120℃; for 12h; Inert atmosphere;
  • 29
  • [ 1022094-52-5 ]
  • [ 178396-31-1 ]
  • (Z)-methyl 4-(3-(6-bromoquinolin-8-yl)-2-fluoroprop-1-en-1-yl)benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
63% With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; zinc diacetate; calcium hydroxide; silver(I) triflimide In 2,2,2-trifluoroethanol at 45℃; for 24h; Molecular sieve; Inert atmosphere; Sealed tube; stereoselective reaction;
  • 30
  • [ 2446-83-5 ]
  • [ 178396-31-1 ]
  • diisopropyl 1-((6-bromoquinolin-8-yl)methyl)hydrazine-1,2-dicarboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% With silver hexafluoroantimonate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; lithium acetate; lithium carbonate In 1,2-dichloro-ethane at 120℃; for 20h;
  • 31
  • [ 20452-67-9 ]
  • [ 178396-31-1 ]
  • C20H18BrNO [ No CAS ]
YieldReaction ConditionsOperation in experiment
89% With silver hexafluoroantimonate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer In 1,2-dichloro-ethane at 45℃; for 20h; regioselective reaction;
  • 32
  • [ 178396-31-1 ]
  • [ 611-73-4 ]
  • (6-bromoquinolin-8-yl)methyl 2-oxo-2-phenylacetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% With tris-(dibenzylideneacetone)dipalladium(0); [bis(acetoxy)iodo]benzene In chloroform at 70℃; for 12h; Sealed tube; regiospecific reaction;
80% With tris-(dibenzylideneacetone)dipalladium(0); [bis(acetoxy)iodo]benzene In chloroform at 70℃; for 12h; Sealed tube; 8 Example 8 6-bromo-8-methylquinoline (22.1 mg, 0.1 mmol),Benzoylformic acid (30.0 mg, 0.2 mmol), tris(dibenzylideneacetone)dipalladium (9.2 mg, 0.01 mmol), iodobenzene diacetate (80.5 mg, 0.25 mmol),A stir bar was placed in the reaction tube, and 1 ml of a solvent CHCl 3 was added to seal the reaction tube.The reaction tube was placed in a 70 ° C oil bath reaction pot and stirred for 12 hours. After cooling to room temperature,It was neutralized with a saturated sodium hydrogencarbonate solution and extracted with ethyl acetate. The combined extracts were dried over anhydrous sodium sulfate, filtered and evaporated.Petroleum ether = 1 : 4 (volume ratio) as an eluent The crude product was subjected to column chromatography to give a pure product. Yellow solid, melting point 47-49 ° C, yield 80%.
  • 33
  • [ 178396-31-1 ]
  • [ 73183-34-3 ]
  • 8-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
59.5% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,2-dimethoxyethane at 80℃; for 12h; Inert atmosphere; 1.1 8-Methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinoline 1b 6-Bromo-8-methylquinoline 1a (444 mg, 2.00 mmol, prepared according to the known method disclosed in "Journal of Organic Chemistry, 2014, 79(11), 5379-5385"), bis(pinacolato)diboron (508 mg, 2.00 mmol), [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium (292 mg, 0.40 mmol) and potassium acetate (588 mg, 6.00 mmol) were dissolved successively in 10 mL of glycol dimethyl ether under an argon atmosphere. The reaction solution was heated to 80°C, and stirred for 12 hours. The reaction was stopped, and the reaction solution was cooled to room temperature and filtrated. The filtrate was added with 20 mL of ethyl acetate, washed with water (10 mL) and saturated sodium chloride solution (10 mL) successively, dried over anhydrous sodium sulfate, and filtrated. The filtrate was concentrated under reduced pressure, and the residue was purified by thin layer chromatography with developing solvent system B to obtain the title product 1b (320 mg), yield: 59.5%. MS m/z (ESI): 270.1 [M+1].
59.5% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate at 80℃; for 12h; Inert atmosphere; 5.1 Step 1
8-Methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinoline 5c 6-Bromo-8-methylquinoline 5b (444 mg, 2.00 mmol, prepared according to the known method disclosed in ""), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) 5a (508 mg, 2.00 mmol), [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium (292 mg, 0.40 mmol) and potassium acetate (588 mg, 6.00 mmol) were dissolved successively in 10 mL of glycol dimethyl ether under an argon atmosphere. The reaction solution was heated to 80°C, and stirred for 12 hours. The reaction was stopped, and the reaction solution was cooled to room temperature and filtrated. The filtrate was added with 20 mL of ethyl acetate, washed successively with water (10 mL) and saturated sodium chloride solution (10 mL), dried over anhydrous sodium sulfate, and filtrated. The filtrate was concentrated under reduced pressure, and the residue was purified by thin layer chromatography with developing solvent system B to obtain the title compound 5c (320 mg, yield: 59.5%).
With bis-triphenylphosphine-palladium(II) chloride; potassium acetate In 1,4-dioxane at 120℃; for 0.5h; Inert atmosphere; Microwave irradiation; S23.1 Step 1 ;Synthesis of 8-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinoline To a solution of 6-bromo-8-methylquinoline (100 mg, 0.45 mmol, 1 eq.) in 1,4-dioxane (10 mL) was added 5-(4,4,5,5-bis(pinacolato)diboron (127 mg, 0.49 mmol, 1.1 eq.), KOAc (88 mg, 0.90 mmol, 2 eq.), PdCl2(PPh3)2(15.7 mg, 0.02 mmol, 0.05 eq.). The reaction mixture was deoxygenated with N2 and the reaction mixture was heated under microwave irradiation for 30 min at 120° C. The reaction was monitored by LCMS and found to be complete after 30 min. The reaction mixture was cooled to RT, diluted with water (10 mL) and extracted with ethyl acetate (2*20 mL). Combined organic layer was washed with brine (20 mL) and dried over sodium sulfate. Removal of solvent under reduced pressure gave crude (150 mg) which was carried to next step without any further purification.
  • 34
  • silver hexafluoroantimonate [ No CAS ]
  • 2-methyl-non-2-en-4-yne [ No CAS ]
  • [ 178396-31-1 ]
  • C20H23BrN(1+)*F6Sb(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
79% With [Cp*Rh(OAc)2]; silver(I) acetate In 1,2-dichloro-ethane at 100℃; regioselective reaction;
79% With [Cp*Rh(OAc)2]; silver(I) acetate In 1,2-dichloro-ethane at 100℃; for 24h; Inert atmosphere; Sealed tube; Irradiation; 16 example 16: Under the protection of inert gas, [Cp*Rh(OAc)2] (8mol%), AgSbF6 (0.2mmol), was added to the sealed tube.AgOAc (0.3 mmol) and DCE (2.0 mL) were stirred for 10 minutes under backlight conditions.Compound 1j (0.2 mmol) and compound 2a (0.3 mmol) were subsequently added.The reaction was carried out in an oil bath at 100 ° C, after completion of the reaction (24 hours),The sealed tube was taken out of the oil bath and cooled to ambient temperature.The reaction was filtered through Celite, using DCM: MeOH = 10: 1 was eluted and concentrated.The crude product is then transferred to a tube with a magnetic stir bar.DCM (2.0 mL), water (2.0 mL) and NasbF6 (100 mg) were then added at room temperature.After the reaction mixture was stirred for 10 min, the org.The organic layer was evaporated and purified by silica gel chromatography elutingThe product 3ja was obtained.
  • 35
  • [ 21652-58-4 ]
  • [ 178396-31-1 ]
  • C20H10BrF16N [ No CAS ]
YieldReaction ConditionsOperation in experiment
89% With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; zinc diacetate; calcium hydroxide; silver(I) triflimide In 2,2,2-trifluoroethanol at 100℃; for 12h; Molecular sieve; Sealed tube; Inert atmosphere; Schlenk technique; stereoselective reaction;
  • 36
  • [ 27126-76-7 ]
  • [ 178396-31-1 ]
  • (6-bromoquinolin-8-yl)methyl 4-methylbenzenesulfonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
57% With palladium diacetate In 1,4-dioxane at 20℃; for 13h; Schlenk technique;
  • 37
  • [ 1809-20-7 ]
  • [ 178396-31-1 ]
  • diisopropyl ((6-bromoquinolin-8-yl)methyl)phosphonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
45% Stage #1: 6-bromo-8-methylquinoline With silver(I) acetate; sodium acetate; palladium diacetate; p-benzoquinone In tert-Amyl alcohol at 120℃; for 0.166667h; Sealed tube; Inert atmosphere; Stage #2: diisopropyl hydrogenphosphonate In tert-Amyl alcohol at 120℃; for 10h; Sealed tube; Inert atmosphere; chemoselective reaction;
  • 38
  • [ 178396-31-1 ]
  • potassium trifluoro(methyl)boranuide [ No CAS ]
  • [ 91348-33-3 ]
YieldReaction ConditionsOperation in experiment
52% With silver hexafluoroantimonate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; silver carbonate In 1,2-dimethoxyethane at 100℃; for 48h; regioselective reaction;
  • 39
  • [ 178396-31-1 ]
  • [ 140-88-5 ]
  • ethyl 4-(6-bromoquinolin-8-yl)butanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
61% With silver hexafluoroantimonate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; 1,1,1,3',3',3'-hexafluoro-propanol; Trimethylacetic acid at 120℃; for 24h; Inert atmosphere; Glovebox; regioselective reaction;
  • 40
  • [ 178396-31-1 ]
  • [ 121219-12-3 ]
  • 6-bromo-8-(4-pentylbenzyl)quinoline [ No CAS ]
  • 41
  • [ 1679-18-1 ]
  • [ 178396-31-1 ]
  • 8-(bis(4-chlorophenyl)methyl)-6-bromoquinoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; trifluoromethylsulfonic anhydride; silver(l) oxide In 1,2-dichloro-ethane at 100℃; for 24h; Inert atmosphere; Sealed tube; chemoselective reaction;
  • 42
  • [ 930-88-1 ]
  • [ 178396-31-1 ]
  • 3-((6-bromoquinolin-8-yl)methyl)-1-methyl-1H-pyrrole-2,5-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
77% With silver hexafluoroantimonate; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; oxygen; copper diacetate In 1,4-dioxane at 70℃; for 30h; Schlenk technique;
  • 43
  • [ 3240-34-4 ]
  • [ 178396-31-1 ]
  • (6-bromoquinolin-8-yl)methyl acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With tris(acetonitrile)(η5-pentamethylcyclopentadienyl)rhodium(III) hexafluoroantimonate; acetic anhydride In 1,2-dimethoxyethane at 100℃; for 6h; Schlenk technique; Inert atmosphere; Sealed tube;
71% With tris-(dibenzylideneacetone)dipalladium(0); potassium peroxodisulfate In 1,2-dichloro-ethane at 20℃; for 1h;
  • 44
  • [ 178396-31-1 ]
  • 6-bromoquinoline-8-carbaldehyde [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% Stage #1: 6-bromo-8-methylquinoline With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In 1,2-dichloro-ethane for 5h; Reflux; Stage #2: In water for 5h; Reflux;
  • 45
  • [ 1679-18-1 ]
  • [ 178396-31-1 ]
  • 6-bromo-8-(4-chlorobenzyl)quinoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
58% With [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; silver trifluoromethanesulfonate; copper(II) bis(trifluoromethanesulfonate); silver(l) oxide In tetrahydrofuran; 2,2,2-trifluoroethanol at 100℃; for 12h; Inert atmosphere; chemoselective reaction;
  • 46
  • [ 5176-28-3 ]
  • [ 178396-31-1 ]
  • tert-butyl (2-((6-bromoquinolin-8-yl)methyl)-1,2-dihydronaphthalen-1-yl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% With silver hexafluoroantimonate; carbonyl(pentamethylcyclopentadienyl)cobalt diiodide; iron(II) acetate at 70℃; for 24h; Inert atmosphere; Schlenk technique;
  • 47
  • [ 178396-31-1 ]
  • [ 86396-02-3 ]
  • 2-((6-bromoquinolin-8-yl)methyl)-3-hydroxycyclohex-2-en-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
84% With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; silver(I) acetate at 80℃; for 12h; Sealed tube;
  • 48
  • [ 178396-31-1 ]
  • [ 458532-84-8 ]
  • 6-bromo-8-((2-chloropyridin-4-yl)methyl)quinoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
74% With [Cp*Rh(MeCN)3](SbF6)2; lithium fluoride; silver(l) oxide In chlorobenzene for 21h; Schlenk technique; Sealed tube; Inert atmosphere; Heating;
  • 49
  • [ 178396-31-1 ]
  • 1-((trifluoromethyl)thio)pyrrolidine-2,5-dione [ No CAS ]
  • 6-bromo-8-(((trifluoromethyl)thio)methyl)quinoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
77% With silver hexafluoroantimonate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; 1,1,1,3',3',3'-hexafluoro-propanol; sodium carbonate at 80℃; for 24h; Inert atmosphere; Glovebox; Molecular sieve;
  • 50
  • [ 178396-31-1 ]
  • 6-bromo-8-(iodomethyl)quinoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% With tris-(dibenzylideneacetone)dipalladium(0); [bis(acetoxy)iodo]benzene; iodine In 1,2-dichloro-ethane at 20℃; for 0.5h;
Same Skeleton Products
Historical Records

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