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CAS No. : | 21190-87-4 | MDL No. : | MFCD00093197 |
Formula : | C6H4BrNO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | XURXQNUIGWHWHU-UHFFFAOYSA-N |
M.W : | 202.01 | Pubchem ID : | 593919 |
Synonyms : |
|
Chemical Name : | 6-Bromo-2-pyridinecarboxylic acid |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
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 |
---|---|---|
100% | With bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; | 4-[(6-Bromo-pyridine-2-carbonyl)-amino]-1-methyl-1H-pyrazole-3-carboxylic acid methyl ester A mixture of 6-Bromo-pyridine-2-carboxylic acid (3000 mg; 14.85 mmol; 1.00 eq.), 4-Amino-1-methyl-1H-pyrazole-3-carboxylic acid methyl ester (2765 mg; 17.82 mmol; 1.20 eq.), Ethyl-diisopropyl-amine (6.57 mL; 37.13 mmol; 2.50 eq.) and 3-[chloro-(2-oxooxazolidin-3-yl)phosphoryl]oxazolidin-2-one (4536 mg; 17.82 mmol; 1.20 eq.) in DCM (20 mL) were stirred at RT for overnight. The reaction was filtered, the solid was washed with water, and then acetonitile, the title compound was obtained as a white solid. The filtrate was washed with water, the organic layer was separated, concentrated, washed with methanol, and collected the title compound (combined portions: gave product 5000 mg, which was quantitative yield). LC-MS (M+1): 339/341. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
23% | With acetic acid; at 70℃; for 12h; | 6-bromo-2-picolinic acid 2 (0.40 g, 2.00 mmol), tetraaminobenzene hydrochloride 3 (0.28 g, 1.00 mmol) in glacial acetic acid,The reaction was stirred at 70 ° C for 12 hours.After cooling to room temperature, filter the diatomaceous earth.Wash the dichloromethane several times until there is no product.Spin the solvent and separate it by column chromatography.Yellow solid 1 was obtained as the objective product (0.11 g, yield 23percent). The target product was confirmed by nuclear magnetic resonance spectroscopy. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
6.9% | General procedure: The corresponding carboxylic acid (1 equiv), benzotriazol-1-yloxytripyrrolidinophosphoniumhexafluorophosphate (PyBOP) (1equiv), and triethylamine (TEA) (3 equiv) were dissolved in anhydrousDMF under argon and stirred for 15 min at RT. The appropriate primaryamine (2 equiv) was then added in one portion and the reaction wasallowed to stir for 18 h at RT and then poured into 75 mLs EtOAc and25 mLs deionized water. The aqueous layer was discarded and the organiclayer was washed twice with water (25 mLs) and once with brine(25 mLs). The organic layer was dried with magnesium sulfate andevaporated under reduced pressure. The crude solids were purified byflash chromatography (5-20% EtOAc/Hexanes) to afford pure products. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
900 mg | To the suspension of 6-bromopicolinic acid (scheme 8-32 compound S1, 606 mg, 3.0mmol) in DCM (15.0mL), a catalytic amount of DMF was added, followed by dropwise addition of oxalyl chloride (495 mg, 3.9mmol, 0.34mL) at 0 C. The reaction mixture was warmed up to rt and kept stirring for additional 1 h. The volatiles were evaporated and the remaining material was dissolved in DCM (15.0 mL). The solution was cooled in an ice bath. To the solution, <strong>[140645-24-5]tert-butyl (S)-3-(aminomethyl)piperidine-1-carboxylate</strong> (535 mg, 2.5mmol) was added, followed by addition of TEA. The mixture was stirred overnight and quenched with saturated NaHCO3. The two layers are separated and the organic phase was dried over MgSO4, filtered and concentrated. The residue was purified to afford the title compound (900 mg). LC (method A): tR = 2.21min. LC/MS (EI) m/z: [M + H]+ 398.34, 400.37 |
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