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CAS No. : | 128071-75-0 | MDL No. : | MFCD04966945 |
Formula : | C6H4BrNO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | GNFWMEFWZWXLIN-UHFFFAOYSA-N |
M.W : | 186.01 | Pubchem ID : | 4714951 |
Synonyms : |
|
Chemical Name : | 2-Bromonicotinaldehyde |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H317-H319 | 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 |
---|---|---|
With sodium hydroxide; sodium tris(acetoxy)borohydride; In acetic acid; 1,2-dichloro-ethane; | Step A N-((2-Bromo(3-pyridyl))methyl)-<strong>[5754-35-8]2-(1,3-dioxolan-2-yl)ethylamine</strong> To a solution of 2-bromopyridine-3-carbaldehyde (3.53 g, 19.0 mmol, 1.0 eq) (Melnyk et al., Synthetic Commun. 23(19):2727-2730, 1993) in 1,2-dichloroethane (50 mL) was added <strong>[5754-35-8]2-(1,3-dioxolan-2-yl)ethylamine</strong> (TCI-GR, 2.67 g, 22.8 mmol, 1.2 eq), sodium triacetoxyborohydride (Aldrich, 1.61 g, 76 mmol, 4.0 eq) and glacial acetic acid (1.14 g, 19 mmol, 1.0 eq). The reaction mixture was stirred under nitrogen at room temperature for 2 h. The reaction was quenched with 1.0 N aqueous NaOH to about pH 8 and the solution was extracted with EtOAc (200 mL*3). The organic extracts were washed with saturated NaCl, dried with MgSO4, filtered and concentrated. Flash column chromatography (silica gel, 0-10% EtOAc-Hexane) afforded the title compound as a colorless oil. MS m/z 377 (Br=79, M+H), 379 (Br=81, M+H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With sodium sulfate; triethylamine; In tetrahydrofuran; at 80℃; for 3h;Microwave irradiation; | General procedure: In a 20 mL glass tube equipped with septa, the aldehyde, dry Na2SO4 (2.81 equiv) and triethylamine (2 equiv) were suspended in dry THF. Then, the hydroxylamine hydrochloride (2 equiv) was added. The mixture was stirred for 30 s, and then exposed to MWI (250 W) at 80 °C during the time indicated for each compound. When the reaction was over (TLC analysis), the reaction mixture was diluted with water, extracted with CH2Cl2, dried over anhydrous sodium sulphate, filtered and the solvent was evaporated. The resultant solid was purified by column chromatography to give pure compounds. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In tetrahydrofuran; water; for 5h;Reflux; | After 2-bromo-3-formyl-pyridine (1.86 g, 10 mmol) and <strong>[458532-98-4]3-chloro-4-pyridylboronic acid</strong> (1.57 g, 10 mmol) were dissolved in tetrahydrofuran (THF) (30 mL), 2M potassium carbonate aqueous solution (20 mL) was added thereto, and tetrakistriphenylphosphino palladium (Pd(PPh3)4 (231 mg, 2 mol%) was put thereinto, agitated and refluxed for 5 hours. The temperature was lowered to normal temperature, the water layer was removed, and the organic layer was dried with anhydrous magnesium sulfate and filtered. The filtered solution was concentrated under the reduced pressure to prepare the compound A-39 (1.31 g, 60%). MS: [M+H]+=219 |
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