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CAS No. : | 182163-96-8 | MDL No. : | MFCD01075676 |
Formula : | C9H13BO5 | Boiling Point : | No data available |
Linear Structure Formula : | - | InChI Key : | RULQUTYJXDLRFL-UHFFFAOYSA-N |
M.W : | 212.01 | Pubchem ID : | 2734390 |
Synonyms : |
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Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P305+P351+P338 | 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 |
---|---|---|
76% | With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In methanol; water; toluene;Inert atmosphere; Reflux; | General procedure: To a solution of bromobiphenylaldehyde (6, 260 mg, 1 mmol) and various phenyl boronic acids (7a-j, 1 mmol) in 2 M aqueous sodium carbonate (2 mL) and toluene/ethanol (9:3 mL) is added a catalytic amount (0.4% mol) of tetrakis-triphenylphosphine palladium, and the mixture was reflux under argon atmosphere for 2-3 h. After completion of reaction, the suspension is cooled and extracted with ethyl acetate (3 × 30 mL) and the organic phase was washed with water and brine, dried over anhydrous Na2SO4 and the solvent was removed under reduced pressure to get the crude product. This residue was further purified by column chromatography using ethyl acetate and hexane to afford the pure terphenylaldehydes (8). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1.0 g | With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,4-dioxane; water; at 90℃; for 12h; | [13011 6-Bromo-3 -(3,4,5 -trimethoxyphenyl)imidazo [1 ,2-a]pyridine can be prepared asshown in Scheme 44: A reaction flask was charged with <strong>[474706-74-6]6-bromo-3-iodoimidazo[1,2-a]pyridine</strong> (2.0 g, 6.2 mmol), (3,4,5-trimethoxyphenyl)boronic acid (1.44 g, 6.8 mmol), 2M. aq. Na2CO3 (8 mL, 16 mmol), 1 ,4-dioxane (50 mL) and a stir bar. The contents were degassed by vacuum and back filled with argon in three times while stirring. Subsequently, catalyst Pd(PPh3)4 (0.35 g, 0.30 mmol) was added to the reaction contents, repeated degassing cycles and heated at 90 C for 12h. Reaction mixture was cooled and filtered the biphasic reaction mixture through Celite and concentrated the filtrate. The crude solid residue was partitioned between CH2C12(150 mL)/water (50 mL). The organic layer was separated, dried over Mg504, filtered and concentrated. The crude concentrate (2.2 g) was subjected to purification by flash column chromatography (Combiflash companion system with RediSep silica gel column 40 g, 30-60% EtOAC/hexanes as an eluting solvent) to obtain 6-bromo-3 -(3,4,5 -trimethoxyphenyl)imidazo [1 ,2-a]pyridine as a white solid(1.0 g). |