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CAS No. : | 874792-20-8 | MDL No. : | MFCD04036192 |
Formula : | C10H8BrNO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | AWLGLUBASOBKNM-UHFFFAOYSA-N |
M.W : | 238.08 | Pubchem ID : | 45790929 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | 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 |
---|---|---|
90.8% | In methanol; at 20 - 120℃; for 15h; | To a solution of 6-bromo-4-chloro-quinoline (12.12 g, 50 mmol) in methanol (200 mL) was added sodium methoxide (13.50 g, 250 mmol) at room temperature. Then, the reaction mixture was heated to 120 C. for 15 h in a sealed reaction flask. After cooling to room temperature, the methanol was removed under the vacuum and the residue was diluted with water. Then, the solids were collected by filtration and washed with water. After drying in air, 10.8 g (90.8% yield) of 6-bromo-4-methoxy-quinoline was isolated as a white solid which can be crystallized from acetonitrile: EI-HRMS m/e calcd for C10H8BrNO (M+) 236.9789, found 236.9784. |
36% | In methanol; at 120℃; for 1h;Microwave irradiation; | 300 mg (1.24 mmol) of 6-bromo-4-chloroquinoline [Lin et al., J. Med. Chem. 1978, 21, 268] was taken up in 4 ml methanol and 1.15 ml (6.19 mmol) methanolic sodium methylate solution (30 wt.%) was added. Then it was reacted in a single mode microwave for 1 h at 1200C. The solvent was removed in a rotary evaporator and the residue was partitioned between water and ethyl acetate. The aqueous phase was extracted with ethyl acetate and the combined organic phases were dried over magnesium sulfate. The solvent was removed by distillation at reduced pressure. In this way we obtained 150 mg (36% of theor.) of the target compound.LC-MS (method 2): R, = 1.24 min; MS (EIpos): m/z = 238 [M]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium acetate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In 1,4-dioxane; at 110℃;Inert atmosphere; | Under an argon atmosphere, 150 mg of example 87A was dissolved in 4 ml dioxane. Then 111.3 mg (1.134 mmol) potassium acetate, 41.2 mg (0.050 mmol) of 1, l'-bis-(diphenylphosphino)- ferrocene palladium(II) chloride-dichloromethane complex and 176 mg (0.693 mmol) of 4,4,4'4'5,5,5'5'-octamethyl-2,2'-bi-l,3,2-dioxaborolan were added. The reaction mixture was stirred overnight at 1100C oil bath temperature. After cooling, dichloromethane was added to the reaction mixture and it was filtered on kieselguhr. It was washed again with ethyl acetate. The filtrate was concentrated in a rotary evaporator at reduced pressure and dried under high vacuum. We obtained 227 mg of 4-methoxy-6-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)quinoline [47%, (LC-MS)] as raw product. This was reacted subsequently without further purification. |