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Chemical Structure| 63050-11-3 Chemical Structure| 63050-11-3

Structure of 63050-11-3

Chemical Structure| 63050-11-3

Ethyl 2-(bromomethyl)nicotinate

CAS No.: 63050-11-3

4.5 *For Research Use Only !

Cat. No.: A643587 Purity: 95+%

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Product Details of [ 63050-11-3 ]

CAS No. :63050-11-3
Formula : C9H10BrNO2
M.W : 244.09
SMILES Code : O=C(OCC)C1=C(CBr)N=CC=C1
MDL No. :MFCD05738912

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Application In Synthesis of [ 63050-11-3 ]

* 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 [ 63050-11-3 ]

[ 63050-11-3 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 1721-26-2 ]
  • [ 63050-11-3 ]
  • 2-Dibromomethyl-nicotinic acid ethyl ester [ No CAS ]
  • 2
  • [ 1721-26-2 ]
  • [ 63050-11-3 ]
YieldReaction ConditionsOperation in experiment
59.4% With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); In tetrachloromethane; for 8h;Inert atmosphere; Reflux; Under a nitrogen atmosphere, <strong>[1721-26-2]ethyl 2-methylnicotinate</strong> (1.65 g, 10 mmol) was dissolved in carbon tetrachloride, and N-bromosuccinimide (2.31 g, 13 mmol) and azoisobutyronitrile (164 mg, 1 mmol) were added thereto. The mixture was refluxed for 8 hours. After the completion of the reaction was confirmed by HPLC, the reaction mixture was allowed to cool down to a room temperature. The organic layer was washed with water 3 times and then with a saturated saline solution, and dried over magnesium sulfate. After the solvent was distilled off, the resulting residue was purified by flash column chromatography (Yamazen, Hi-Flash column, silica gel, hexane/ethyl acetate (volume ratio)=10:1) to give the title compound (1.45 g, 59.4percent) as an oily substance. 1H-NMR (CDCl3, delta): 1.39 (3H,t,J=7.3 Hz), 4.42 (2H,q,J=7.3 Hz), 5.04 (2H,s), 7.34 (1H,app-dd,J=4.6, 7.8 Hz), 8.29 (1H,dd,J=1.9, 8.1 Hz), 871 (1H,dd,J=1.6, 4.6 Hz)
49% With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); In tetrachloromethane; at 90℃; for 16h; A mixture of <strong>[1721-26-2]ethyl 2-methylnicotinate</strong> (3.1 mL, 20 mmol), azoisobutyronitrile (300 mg, 1.83 mmol) and N-bromosuccinimide (4.6 g, 26 mmol) in carbon tetrachloride (70 mL) was heated to 90° C. for 16 hours. The solution was filtered, the precipitate was washed with carbon tetrachloride, and the combined solutions were washed with saturated bicarbonate (2*) and brine, dried over magnesium sulfate and concentrated to dryness. The product was isolated by flash-chromatography (dichloromethane) as an oil (2.37 g, 49percent).
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); acetic acid; In tetrachloromethane; for 4h; Stage A 8 ml (51.6 mmoles) of <strong>[1721-26-2]ethyl 2-methylnicotinate</strong> is dissolved in 93 ml of carbon tetrachloride. Then 2.9 ml of acetic acid, 17.73 g of N-bromosuccinimide and 0.185 g of AIBN are added. The mixture is placed under a 500 W lamp for 4 ours. Then the red solution and the gum obtained are poured into an ice-cold solution of sodium bicarbonate. The aqueous phase is extracted with dichloromethane, dried and the solvent is evaporated off under reduced pressure. 14.74 g of red oil is obtained containing the expected brominated derivative. Then the oil obtained is dissolved in 90 ml of anhydrous THF in the presence of 6 ml of triethylamine and 15 g (72 mmoles) of tert-butyl N-benzyl-glycinate. Agitation is carried out for 24 hours at ambient temperature, followed by diluting with water then extracting with ethyl acetate. The organic phase is dried over magnesium sulphate then the solvent is evaporated off under reduced pressure. 25 g of product is obtained in the form of a resin which is purified by chromatography on silica eluding with a cyclohexane/ethyl acetate mixture (80/20). After evaporation of the solvent, 14.18 g of ethyl 2-[[[2-(1,1-dimethylethoxy)-2-oxoethyl](phenylmethyl)amino]methyl]-3-pyridinecarboxylate, of molecular formula C21H26N2O4 (M=370.45 g) is obtained in the form of an orange-coloured oil. The yield obtained is 71.6percent.
With N-Bromosuccinimide; dibenzoyl peroxide; In acetic acid methyl ester; at 110 - 130℃; for 1.16667h;Microwave irradiation; 2.3 Example 3 (prepared according to Scheme 3)6-((3-Cyclobutyl-2,3,4,5-tetrahydro-lH-3-benzazepin-7-yl)methyl)-6,7-dihyd:pyrrolo[3,4-b]pyridin-5-oneStep a) Intermediate 8Ethyl 2-(bromomethyl)pyridine-3-carboxylate A mixture of <strong>[1721-26-2]ethyl 2-methyl nicotinate</strong> (1 ml, 6.49 mmol), NBS (1.15 g, 6.49 mmol) and benzoyl peroxide (0.08 g, 0.32 mmol) in methyl acetate (2 ml) was heated under microwave conditions at 1 10 °C for 1 h, then 130 °C for a further 10 min. EtOAc (250 ml) and aqueous saturated sodium metabisulphite solution (250 ml) were added and the mixture stirred and the layers separated. The organics were washed with more sodium metabisulphite (150 ml), dried (MgSC^) and evaporated to yield ethyl 2-(bromomethyl)pyridine-3-carboxylate as a brown liquid in ~ 20 percent purity. MS (ES+) 244/246
1 g With N-Bromosuccinimide; dibenzoyl peroxide; In tetrachloromethane; at 100℃; for 6h; To a solution of <strong>[1721-26-2]ethyl 2-methylnicotinate</strong> (1 g, 6.05 mmol) in CCl4 (30 ml) was added N- bromosuccinimide (2.15 g, 12.1 mmol) and benzoyl peroxide (2.19 g, 9.07 mmol). The reaction mixture was heated to 100 °C and stirred at that temperature for 6 h. Water (20 mL) was added to the reaction vessel and was extracted with DCM(3 x 20 mL). The layers were separated and the organic phase was washed with saturated aqueous NaCl (2 x 20 mL). The combined organics were dried over anhydrous Na2SO4, filtered and concentrated in vacuo. After concentration, the residue was purified by silica column chromatography (Hexanes: EtOAc = 10:1) to give the desired product (1 g) as a yellow oil.
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); In tetrachloromethane; at 50℃; for 0.75h;UV-irradiation; Intermediate 25; (3-Ethoxycarbonyl-pyridin-2-ylmethyl)-trimethyl-phosphonium Bromide; A stirred mixture of N-bromosuccinimide (5.6 g, 31 mmol), 2-Methyl-nicotinic acid ethyl ester (4.1 g, 24 mmol), AIBN (0.05 g, 0.3 mmol) in 50 mL of carbon tetrachloride at 500C is irradiated with a 250 Watt heat lamp for 45 minutes. The reaction was cooled to room temperature and is poured into saturated sodium bicarbonate. The products are extracted into dichloromethane and the combined organic layers are dried over sodium sulfate, filtered, and concentrated under reduced pressure to afford a residue which is immediately dissolved in 100 mL of toluene. To the solution is added triphenyl phosphine (8.1 g, 31 mmol) and the reaction is heated at reflux for 2 hours. The heat source is removed and filtration gives the title compound. 1HNMR MS (m/e): 426 (M+l)

  • 3
  • [ 1721-26-2 ]
  • [ 13822-09-8 ]
  • [ 63050-11-3 ]
YieldReaction ConditionsOperation in experiment
With N-Bromosuccinimide; In tetrachloromethane; EXAMPLE 152A Ethyl 2-bromomethylpyridine-3-carboxylate Ethyl 2-methylpyridine-3-carboxylate is refluxed with N-bromosuccinimide in carbon tetrachloride with 1percent equivalent dibenzyl peroxide to give the title compound.
 

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