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[ CAS No. 911210-49-6 ]

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Chemical Structure| 911210-49-6
Chemical Structure| 911210-49-6
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Product Details of [ 911210-49-6 ]

CAS No. :911210-49-6 MDL No. :MFCD10697414
Formula : C8H8BNO2 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W :160.97 g/mol Pubchem ID :-
Synonyms :

Safety of [ 911210-49-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 911210-49-6 ]

  • Downstream synthetic route of [ 911210-49-6 ]

[ 911210-49-6 ] Synthesis Path-Downstream   1~9

  • 1
  • [ 156001-51-3 ]
  • [ 911210-49-6 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 3-Bromo-6-methyl-benzonitrile With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.583333h; Stage #2: With Triisopropyl borate In tetrahydrofuran; hexane at -78℃; for 1h; Stage #3: With hydrogenchloride; water In tetrahydrofuran; hexane at -78 - 20℃; 61.a 17.5 ml of n-butyllithium solution (1.6M in hexane) are added dropwise to a solution of 5 g of 5-bromo-2-methylbenzonitrile in 80 ml of dry tetrahydrofuran at -78°C. After stirring at this temperature for 35 minutes, 7.3 ml of triisopropyl borate are added. After one hour, 50 ml of 1 N HCl are added to the reaction mixture at -78°C, and the mixture is warmed to room temperature. The phases are separated and the aqueous phase is extracted three more times with 100 ml of diethyl ether each time. The combined organic phases are dried with sodium sulphate, and the solvent is concentrated to 5 ml. The residue is mixed with 150 ml of pentane. The precipitate which has separated out is filtered off with suction and washed twice with pentane. Drying under high vacuum results in 2.85 g of the title compond as a pale yellow solid. Rt = 2.98.
Stage #1: 3-Bromo-6-methyl-benzonitrile With n-butyllithium In tetrahydrofuran; hexane at -78℃; Stage #2: With Triisopropyl borate In tetrahydrofuran; hexane for 1h; Stage #3: With hydrogenchloride; water In tetrahydrofuran; hexane at -78 - 20℃; 61.a 17.5 ml of n-butyllithium solution (1.6M in hexane) are added dropwise to a solution of 5 g of 5-bromo-2-methylbenzonitrile in 80 ml of dry tetrahydrofuran at -78° C. After stirring at this temperature for 35 minutes, 7.3 ml of triisopropyl borate are added. After one hour, 50 ml of 1N HCl are added to the reaction mixture at -78° C., and the mixture is warmed to room temperature. The phases are separated and the aqueous phase is extracted three more times with 100 ml of diethyl ether each time. The combined organic phases are dried with sodium sulphate, and the solvent is concentrated to 5 ml. The residue is mixed with 150 ml of pentane. The precipitate which has separated out is filtered off with suction and washed twice with pentane. Drying under high vacuum results in 2.85 g of the title compond as a pale yellow solid. Rt=2.98.
Stage #1: 3-Bromo-6-methyl-benzonitrile With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.583333h; Stage #2: With Triisopropyl borate In tetrahydrofuran; hexane at -78℃; for 1h; Stage #3: With hydrogenchloride; water In tetrahydrofuran; hexane at -78 - 20℃; 61.a 17.5 ml of n-butyllithium solution (1.6M in hexane) are added dropwise to a solution of 5 g of 5-bromo-2-methylbenzonitrile in 80 ml of dry tetrahydrofuran at -78°C. After stirring at this temperature for 35 minutes, 7.3 ml of triisopropyl borate are added. After one hour, 50 ml of 1 N HCI are added to the reaction mixture at -78°C, and the mixture is warmed to room temperature. The phases are separated and the aqueous phase is extracted three more times with 100 ml of diethyl ether each time. The combined organic phases are dried with sodium sulphate, and the solvent is concentrated to 5 ml. The residue is mixed with 150 ml of pentane. The precipitate which has separated out is filtered off with suction and washed twice with pentane. Drying under high vacuum results in 2.85 g of the title compond as a pale yellow solid. Rt = 2.98.
  • 3
  • [ 911210-49-6 ]
  • tert-Butyl 2-((2-bromoquinolin-4-yl) (hydroxy)methyl)piperidine-1-carboxylate [ No CAS ]
  • tert-butyl (S)-2-((R)-(2-(3-cyano-4-methylphenyl)quinolin-4-yl)(hydroxy)methyl)piperidine-1-carboxylate [ No CAS ]
  • tert-butyl (R)-2-((S)-(2-(3-cyano-4-methylphenyl)quinolin-4-yl)(hydroxy)methyl)piperidine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
In 1,4-dioxane Mixture of tert-butyl (R)-2-((S)-(2-bromoquinolin-4-yl) (hydroxy)methyl)piperidine-1-carboxylate and tert-butyl (S)-2-((R)-(2-bromoquinolin-4-yl) (hydroxy)methyl)piperidine-1-carboxylate (Intermediate 27) and mixture of tert-butyl (R)-2-((R)-(2-bromoquinolin-4-yl) (hydroxy)methyl)piperidine-1-carboxylate tert-butyl (S)-2-((S)-(2-bromoquinolin-4-yl) (hydroxy)methyl)piperidine-1-carboxylate (Intermediate 28) The relative stereochemistry of the intermediates 27 and 28, respectively, were determined by comparison to the relative retention order of the same intermediates in the synthesis of compounds S20-S23. A solution of intermediate 27 (21 mg, 0.050 mmol), 3-cyano-4-methylphenylboronic acid (10 mg, 0.062 mmol), Pd(dppf)Cl2*CH2Cl2 (2.7 mg, 0.003 mmol) and DIPEA (40 μL, 0.230 mmol) in aqueous dioxane (0.55 mL, 10% H2O) was heated at 80° C. under N2 atmosphere for 15 h. The reaction mixture was diluted with MeCN, filtrated and purified by preparative reverse-phase HPLC using basic conditions. The pure fractions were combined and the solvent was removed under reduced pressure giving a mixture of tert-butyl (S)-2-((R)-(2-(3-cyano-4-methylphenyl)quinolin-4-yl)(hydroxy)methyl)piperidine-1-carboxylate and tert-butyl (R)-2-((S)-(2-(3-cyano-4-methylphenyl)quinolin-4-yl)(hydroxy)methyl)piperidine-1-carboxylate (8.5 mg). MS (ESI+) m/z 458 [M+H]+.
  • 4
  • [ 911210-49-6 ]
  • (erithro) tert-butyl 2-[(2-bromoquinolin-4-yl)hydroxymethyl]piperidine-1-carboxylate [ No CAS ]
  • tert-butyl 2-[[2-(3-cyano-4-methylphenyl)quinolin-4-yl]hydroxymethyl]piperidine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; N-ethyl-N,N-diisopropylamine In 1,4-dioxane; water at 80℃; for 15h; Inert atmosphere;
  • 5
  • [ 911210-49-6 ]
  • (erithro) tert-butyl 2-[(2-bromoquinolin-4-yl)hydroxymethyl]piperidine-1-carboxylate [ No CAS ]
  • (erythro) 5-{4-[hydroxyl(piperidin-2-yl)methyl]quinolin-2-yl}-2-methyl-benzonitrile dihydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; N-ethyl-N,N-diisopropylamine / 1,4-dioxane; water / 15 h / 80 °C / Inert atmosphere 2: hydrogenchloride / dichloromethane; diethyl ether / 24 h / 18 - 25 °C / Inert atmosphere
  • 6
  • [ 911210-49-6 ]
  • C25H18BrN3 [ No CAS ]
  • C33H24N4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
0.96 g With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 120℃; for 72h; 1 Synthesis of Ligand 14 millimoles (mmol) (6.16 grams (g)) of Intermediate 1, 14 mmol (2.25 g) of (3-cyano-4-fluorophenyl)boronic acid, 0.45 mmol (0.52 g) of tetrakis-(triphenylphosphine) palladium (0), and 45 mmol (6.21 g) of potassium carbonate were mixed with 120 milliliters (mL) of a solution of 1,4-dioxane and water (mixed at a volume ratio of 3:1), and the mixed solution was refluxed at a temperature of 120° C. for 72 hours. The reaction mixture was cooled down and extracted by using ethyl acetate and water. The organic layer was washed with water three times and dried by using magnesium sulfate) MgSO4(. The solvent was removed under reduced pressure to obtain a crude product. The crude product was purified by silica gel chromatography (eluent: dichloromethane and hexane), thereby obtaining 2 mmol (0.96 g) of a ligand. The structure and purity of the ligand were identified by NMR, HPLC, and LCMS analyses. 1H NMR (300 MHz, CDCl3, rt): δ 8.80 (d, J=7.26 Hz, 2H), 7.80 (m, 4H), 7.61-7.41 (m, 13H), 7.16 (s, 1H), 6.47 (s, 1H), 2.50 (s, 3H).
  • 7
  • [ 911210-49-6 ]
  • 5-(3-cyano-4-methylphenyl)hex-5-enoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / toluene; water / 80 °C / Inert atmosphere 2: lithium hydroxide monohydrate / methanol; water; tetrahydrofuran / 20 °C
  • 8
  • [ 911210-49-6 ]
  • (S)-5-(2-(bromomethyl)-6-oxotetrahydro-2H-pyran-2-yl)-2-methylbenzonitrile [ No CAS ]
  • (R)-5-(2-(bromomethyl)-6-oxotetrahydro-2H-pyran-2-yl)-2-methylbenzonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / toluene; water / 80 °C / Inert atmosphere 2: lithium hydroxide monohydrate / methanol; water; tetrahydrofuran / 20 °C 3: C27H38N4O6; N-bromophthalimide / acetone / 24 h / -78 °C
  • 9
  • [ 911210-49-6 ]
  • methyl 5-bromohex-5-enoate [ No CAS ]
  • methyl 5-(3-cyano-4-methylphenyl)hex-5-enoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
36% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In water; toluene at 80℃; Inert atmosphere; General procedure for the synthesis of aryl alkenoic acids General procedure: Step 1. Methyl 5-bromohex-5-enoate (6, 1.0 equiv), the specific aryl boronic acid 5a-5h (1.2 equiv), Pd(PPh3)4 (1 mol %), 2.0 M Na2CO3 aq. solution (0.32 M), and toluene (0.20 M) were placed in a round-bottom flask under argon atmosphere. The reaction mixture was stirred at 80 °C overnight. The mixture was treated with sat. aq. NH4Cl and extracted with Et2O. The combined organic extracts were washed with brine, dried (Na2SO4), and filtered, and the solvent was evaporated in vacuo. The residue was purified by flash chromatography on silica (hexanes/EtOAc in various proportions) to afford the coupled product.
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