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CAS No. : | 1214326-89-2 | MDL No. : | MFCD13185327 |
Formula : | C5H4BrFN2 | Boiling Point : | No data available |
Linear Structure Formula : | - | InChI Key : | AANCKJPIOOGVPS-UHFFFAOYSA-N |
M.W : | 191.00 | Pubchem ID : | 53485488 |
Synonyms : |
|
Signal Word: | Warning | Class: | |
Precautionary Statements: | P280-P305+P351+P338-P310 | UN#: | |
Hazard Statements: | H302-H315-H319-H332-H335 | Packing Group: | |
GHS Pictogram: |
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* 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 |
---|---|---|
49% | To a solution of 3-bromo-5- fluoro-pyridin-4-amine (20.0 mmol, 3.82 g) in DMF (40 niL) was added NaH (40.0 mmol, 1.6 g).The mixture was stirred at room temperature for 30 min, then cooled to 0 C. A soluntion of 2-chloro-6-fluoro-benzoyl chloride (30.0 mmol, 5.79 g) in DCM (10 niL) was then added dropwise. The reaction mixture was stirred at room temperature for 16 hours. The reaction was then quenched with ice water, extracted with EtOAc. The combined organics were dried (Na2S04), filtered and concentrated.The resultant oil was dissolved in MeOH (40 mL) and THF (40 mL). 2N NaOH (30 mL) was added. The mixture was stirredat room temperature for 16 hours. The volatile solvents were then removed under reduced pressure. Water (100 mL) was added. The aqueous layer was saturated with NaCl, extracted with CHCL/zPrOH (3/1). The combined organics were dried (Na2S04), filtered and concentrated. The crude product was purified by silica gel chromatography (0-8% EtOAc/DCM) to give the title compound as an off- white solid (3.4 g, 49% yield). ? NMR (400 MHz, DMSO) delta 11.07 (s, IH), 8.74 (s, IH), 8.71 (s, IH), 7.59 (dd, J= 14.8, 7.8 Hz, IH), 7.47 (d, J= 8.1 Hz, IH), 7.40 (t, J= 8.6 Hz, IH). LCMS (ESI) m z 348.9 [M+H+]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | In 1-methyl-pyrrolidin-2-one; at 170℃; for 0.75h;Microwave irradiation; | A mixture of 4-bromo-2-fluoro-pyridin- 3-amine (2.29 g, 12.0 mmol) and potassium ethoxymethanedithioate (3.85 g, 24.0 mmol) in NMP (12 mL) was heated in a microwave at 170 C for 45 min when the reaction mixture turned dark red. The reaction mixture was cooled to 23 C, poured into AcOH and water (10% v/v, 200 mL). The resulting precipitate was collected by filtration to give the title compound (2.94 g, 99% yield) as yellow solid. 1H NMR (400 MHz, DMSO-d6) delta 8.72 (s, 1H), 8.60 (s, 1H). LCMS m/z: 249 [M+H+]. |
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