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CAS No. : | 1190862-68-0 | MDL No. : | MFCD14698212 |
Formula : | C8H7Br2NO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 308.95 | Pubchem ID : | - |
Synonyms : |
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Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P362-P403+P233-P501 | 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 |
---|---|---|
39% | at 85℃; for 48 h; Sealed tube | Step-1 : Methyl 5-bromo-6-methoxynicotinate: To a solution of ethyl-5,6- dibromonicotinate (5.0 g, 16.2 mmol, 1.0 eq) in methanol (5 mL) was added sodium methoxide (2.18g, 40.5 mmol, 2.5 eq) and the resulting mixture was heated in a sealed tube at 85 °C for 48 h. The reaction was cooled back down to RT and the solvent was evaporated under vacuum. The crude residue was taken into water (20 mL) and ethyl acetate (50 mL). The layers were separated and the aqueous layer was extracted with ethyl acetate (2x50 mL). The combined organic layers were washed with brine (50 mL), dried (Na2S04) and filtered. The filtrate was evaporated and the resultant crude product was purified by flash column chromatography (silica gel, ethyl acetate:hexane system as eluent) to afford 1.55 g (39percent) of the desired product as a white solid. HNMR (400 MHz, CDC13) δ 8.76 (d, = 2.0 Hz, 1H), 8.41 (d, = 2.0 Hz, 1H), 4.09 (s, 3H), 3.93 (s, 3H); ESI-MS (m/z) 246, 248 [(MH)+, Br79'81]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45% | With potassium carbonate In 1,4-dioxane at 110℃; for 72 h; Inert atmosphere | An oven-dried resealable Schlenk tube was charged with ethyl 5,6-dibromonicotinate (preparation 47b, 1.09 g, 3.5 mmol), methylboronic acid (0.24 g, 4.0 mmol), potassium carbonate (1.46 g, 10.6 mmol) and 1,4-dioxane (27 mL). The Schlenk tube was subjected to three cycles of evacuation-backfilling with argon, and then tetrakis(triphenylphosphine)palladium(0) (0.41 g, 0.35 mmol) was added. After three new cycles of evacuation-backfilling with argon, the Schlenk tube was sealed and the mixture was stirred and heated in an oil bath to 110 °C. After 3 days, the mixture was cooled, filtered through Celite.(R). and the filtrate was evaporated. Purification of the residue by flash chromatography (97:3 to 9:1 hexanes/ethyl acetate) gave the title compound (0.41 g, 45percent) as a solid. LRMS (m/z): 244/246 (M+1)+. 1H-NMR δ (CDCl3): 1.41 (t, J=9.0Hz, 3H), 2.74 (s, 3H), 4.41 (q, J=9.0Hz, 2H), 8.40 (d, J=3.0Hz, 1H), 9.01 (d, J=3.0Hz, 1H). |