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CAS No. : | 116026-99-4 | MDL No. : | MFCD04035594 |
Formula : | C11H14N2O3 | Boiling Point : | No data available |
Linear Structure Formula : | - | InChI Key : | AHTZIHDCJWVLKK-UHFFFAOYSA-N |
M.W : | 222.24 | Pubchem ID : | 10911130 |
Synonyms : |
|
Chemical Name : | tert-Butyl (2-formylpyridin-3-yl)carbamate |
Signal Word: | Warning | Class: | |
Precautionary Statements: | P305+P351+P338 | UN#: | |
Hazard Statements: | H302-H319 | 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 |
---|---|---|
65% | Step 2: fert-Butyl 2-formylpyridin-3-ylcarbamate (10b)To a solution of compound 10a (2.9 g, 10.7 mmol) in THF (30 mL) was added n-BuLi (2.5M, 8.5 mL, 21.4 mmol) at -78C under N2 atmosphere and the resulting mixture was stirred for 1 h at this temperature. /V-Formylpiperidine (1.3 mL, 11.8 mmol) was added with rapid stirring. The mixture was stirred at 0C for 1 h and then partitioned with 1.5M HCI solution. The pH was adjusted to 7 by the addition of solid Na2C03. The aqueous layer was extracted with EA twice and the combined organic layers were dried over Na2S04, concentrated under reduced pressure and purified by CC (PE/EA = 3/1) to give compound 10b (1.5 g, 65%) as a white solid. | |
64.9% | Add the compound (2-bromopyridin-3-yl) tert-butyl carbamate (20.1 g, 73.3 mmol), 200 mL of dry tetrahydrofuran to a 500 mL three-necked flask, and then N2 replacement protection after the temperature in the reaction flask drops to Slowly add n-BuLi (2.4 M, 73 mL) dropwise after -75C, keep the temperature in the reaction flask not to exceed -65C during the dropwise addition, continue to keep the temperature after the drop, and react for 1 h before adding 4-piperidinaldehyde (9.1 g, 80 mmol), stir for about 10 min after the addition, and then raise the temperature to 0C to react for 1 h. After the reaction was monitored by TLC, saturated ammonium chloride solution was added to quench the reaction, the reaction solution was extracted with ethyl acetate, the organic phases were combined, dried and purified by column chromatography (eluent: ethyl acetate-petroleum ether 1:9) to obtain the compound (2-Formylpyridin-3-yl) tert-butyl carbamate (10.6 g, 64.9%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
43% | Into a 1-L 4-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed <strong>[116026-98-3]tert-butyl N-(2-bromopyridin-3-yl)carbamate</strong> (33.8 g, 123.8 mmol, 1.0 equiv) in THF (500 mL). The reaction was cooled to -78 C. This was followed by the addition of n-BuLi (124.2 mL, 1318.5 mmol, 2.5 equiv) and the reaction stirred for 1 h at the same temperature. DMF (10.9 g, 148.5 mmol, 1.2 equiv) was added and the temperature was allowed to warm to 0 C. Following this, the reaction was stirred for 1 h. The reaction was then quenched by the addition of NH4Cl(aq) (300 mL). The resulting solution was extracted with 3*200 mL of ethyl acetate, dried over anhydrous sodium sulfate, filtered, and concentrated. The residue was purified by silica gel column with ethyl acetate/petroleum ether (3:1). 11.9 g (43%) of tert-butyl N-(2-formylpyridin-3-yl)carbamate was obtained as a yellow solid. LCMS (ES) [M+1]+ m/z: 222. |
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