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CAS No. : | 29682-15-3 | MDL No. : | MFCD04112493 |
Formula : | C7H6BrNO2 | Boiling Point : | No data available |
Linear Structure Formula : | - | InChI Key : | JEURNBCYNWNADN-UHFFFAOYSA-N |
M.W : | 216.03 | Pubchem ID : | 7016458 |
Synonyms : |
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Chemical Name : | Methyl 5-bromopicolinate |
Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | |
Hazard Statements: | H315-H319-H335 | Packing Group: | |
GHS Pictogram: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64% | With tetrakis(triphenylphosphine) palladium(0); cesium fluoride; In 1,2-dimethoxyethane; at 100℃; for 0.25h;Inert atmosphere; Microwave irradiation; | Step 1 To a solution of 5-bromo-pyridine-2-carboxylic acid methyl ester (500 mg, 2.3 mmol, 1 eq) in dimethoxyethane (6 mL) was added <strong>[216019-28-2]3-isopropylphenylboronic acid</strong> (495 mg, 3 mmol, 1.3 eq) and cesium fluoride (1.05 g, 6.9 mmol, 3 eq). The mixture was degassed for 15 min and tetrakis(triphenylphosphine)palladium (133 mg, 0.12 mmol, 0.05 eq) was added. The mixture was heated at 100 C. for 15 min under microwave irradiation. After cooling, the mixture was poured on water (10 mL) and extracted with ethyl acetate (3*20 mL). The organic layers were dried over magnesium sulphate, filtered and evaporated to dryness. The crude residue was purified by flash chromatography using cyclohexane and ethyl acetate (100/0 to 0/100) to afford 5-(3-isopropyl-phenyl)-pyridine-2-carboxylic acid methyl ester as a colorless oil (380 mg, 64% yield). |
64% | With tetrakis(triphenylphosphine) palladium(0); caesium carbonate; In 1,2-dimethoxyethane; at 100℃; for 0.25h;Microwave irradiation; | Step 1 To a solution of 5-bromo-pyridine-2-carboxylic acid methyl ester (500 mg, 2.3 mmol, 1 eq) in dimethoxyethane (6 mL) was added <strong>[216019-28-2]3-isopropylphenylboronic acid</strong> (495 mg, 3 mmol, 1.3 eq) and cesium fluoride (1.05 g, 6.9 mmol, 3 eq). The mixture was degassed for 15 min and tetrakis(triphenylphosphine)palladium (133 mg, 0.12 mmol, 0.05 eq) was added. The mixture was heated at 100 C. for 15 min under microwave irradiation. After cooling, the mixture was poured on water (10 mL) and extracted with ethyl acetate (3*20 mL). The organic layers were dried over magnesium sulphate, filtered and evaporated to dryness. The crude residue was purified by flash chromatography using cyclohexane and ethyl acetate (100/0 to 0/100) to afford 5-(3-isopropyl-phenyl)-pyridine-2-carboxylic acid methyl ester as a colorless oil (380 mg, 64% yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | With caesium carbonate; In 1,4-dioxane; water; at 110℃; for 1.5h;Sealed tube; Microwave irradiation; | General procedure: A mixture 2a or 2b (1 g, 1 equiv.), anappropriate pinacol boronate ester (1.2 equiv.), [1,10-bis(diphenylphosphino)ferrocene]dichloropalladium(II) complex withdichloromethane (10 mol %), cesium carbonate (2.0 equiv.), 1,4-dioxane (8 ml) and water (4 ml) was sealed in a 20 ml microwavereaction vial (Biotage). The vial was irradiated in a microwaveapparatus at 110 C, normal absorption for 30-90 min. The reactionmixture was cooled to room temperature and work up was performedas described in method 1 to obtain the esters 4b-i. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; ruphos; In toluene; at 100℃; for 18h;Inert atmosphere; | Under N2, a mixture <strong>[5978-75-6]9H-<strong>[5978-75-6]fluoren-9-amine hydrochloride</strong></strong> (100 mg, 0.46 mmol) and methyl 5-bromopicolinate (105 mg, 0.49 mmol), tris(dibenzylideneacetone)dipalladium (21 mg, 0.023 mmol), RuPhos (43 mg, 0.092 mmol) and cesium carbonate (450 mg, 1.38 mmol) in toluene (4 ml) was heated at 100 C. for 18 hrs. Then it was cooled to room temperature and filtrated. The filtrate was dissolved in methanol (1 ml) and acetic acid (1 ml). Sodium cyanoborohydride (58 mg, 0.92 mmol) was added at 0 C. It was stirred at 0 C. to room temperature for 6 hrs. Then it was concentrated in vacuo. The residue was mixed with saturated aqueous sodium bicarbonate solution and extracted with EtOAc. The combined organic layers were concentrated in vacuo and the residue was purified by pre-TLC to give compound methyl 5-(9H-fluoren-9-ylamino)picolinate as an oil. (130 mg, 90%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
706 mg | With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In ethanol; water; toluene; for 3h;Reflux; | 10500] A mixture of the Compound 1 (830 mg), the Compound 2 (1.0 g), tetrakis(triphenylphosphine)palladium (802 mg), an aqueous solution of sodium carbonate (2 mol/L, 4.63 mE), toluene (15 mE), ethanol (5 mE), and water (2 mE) was heated under reflux for 3 hours. The reaction mixture was allowed to cool to room temperature, and then ethyl acetate was added thereto, and the resulting mixture was stirred, and then the resulting organic layers were separated, washed with water, dried, and concentrated under reduced pressure. The resulting residues were purified by silica gel column chromatography (hexane:ethyl acetate=90:10 to 55:45) to give the Compound 3 (706 mg) as a colorless powdet MS (APCI): mlz 256 [M+H] |
706 mg | With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In ethanol; water; toluene; for 3h;Reflux; | Compound 1 (830 mg),Compound 2 (1.0 g),Tetrakis (triphenylphosphine) palladium(802 mg),Aqueous sodium carbonate solution(2 mol / L, 4.63 mL),Toluene (15 mL),Ethanol (5 mL),Water (2 mL)Was heated to reflux for 3 hours.The reaction mixture was allowed to cool to room temperature,After adding ethyl acetate and stirring,The organic layer was separated,Wash with water,Dried and concentrated under reduced pressure.The residue was purified by silica gel column chromatography (hexane: ethyl acetate = 90: 10 to 55: 45) to obtain compound 3 (706 mg) as a colorless powder. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
49% | With tetrakis(triphenylphosphine) palladium(0); sodium hydrogencarbonate; In 1,2-dimethoxyethane; water; at 85℃; for 3h;Inert atmosphere; | General procedure: δIn a 100 mL two-necked round-bottomed flask, commercially available Methyl 5-bromopyridine-2-carboxylate (0.75 mmol) and 4-alkoxyboronic acids 2a-e (0.75 mmol) were dissolved in 1,2-dimetoxyethane (15 mL) and then catalytic amount of Pd(PPh3)4 (0.0325 mmol) under Argon atmosphere. To this solution, saturated aqueous solution of NaHCO3 was added and the reaction mixture was heated to reflux for 3 h at 85 C. The end of the reaction was monitored by TLC (hexane: ethyl acetate/3:1). After removing the volatile components in vacuo, the resulting mixture was extracted into CHCl3 (x 3) and the combined organic phases were washed with saturated aqueous NaCl solution and dried over Na2SO4. The solvent was removed under reduced pressure. The residue was dissolved in chloroform and filtered on silica gel in order to remove the catalyst. After evaporation of the solvent, the crude product was purified by column chromatography on silicagel eluting with hexane:ethyl acetate/3:1.The optical rotation of compounds 3d and 3e was measured for the proof of the optical purity.The characterization of the final compounds is based on 1H, 13C NMR (Bruker Avance III 500 spectrometer, in CDCl3 solution, with tetramethylsilane as internal standard). The detection of molecular ions was performed by full MS electrospray ionization [MS ESI (+)].The proposed structures are in full agreement with the spectroscopic data.2.2.2. Methyl 5-(4-n-octyloxyphenyl)pyridine-2-carboxylate (3a)Yield: 49%, 0.125 g; colorless crystals. 1H-NMR (500 MHz,CDCl3): δ(ppm) 8.95 (dd, Jz2.4 Hz and 0.6 Hz, Pyridine Ar-H),8.19 (dd, Jz8.2 Hz and 0.6 Hz, Pyridine Ar-H), 7.99 (dd, Jz8.2 Hzand 2.4 Hz, Pyridine Ar-H), 7.58 (d, Jz8.8 Hz, 2 Ar-H), 7.03 (d,Jz8.8 Hz, 2 Ar-H), 4.04-4.01 (m, 5H, OCH2 and OCH3), 1.85-1.80(m, 2H, CH2), 1.52-1.46 (m, 2H, CH2), 1.41-1.26 (m, 8H, 4 CH2), 0.90(t, Jz7.0 Hz, 3H, CH3). 13C-NMR (125 MHz, CDCl3):δ (ppm) 165.74 (CO), 160.07, 145.68, 139.48, 128.64 (Ar-C), 147.81,134.33, 128.47, 125.22, 115.31 (Ar-CH), 68.22 (OCH2), 52.87 (OCH3),31.80, 29.34, 29.23, 29.19, 26.02, 22.65 (CH2), 14.09 (CH3).C21H27NO3 MW: 341.44 g/mol. Full MS ESI (electrospray ionization)(+) [50.00-1000.00]: 341 (58) [M], 282 (59) [M-C2H3O2], 170(100) [C11H8NO]. |
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