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CAS No. : | 201940-08-1 | MDL No. : | MFCD09953049 |
Formula : | C13H16BrNO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | GOKHEUCWNVPUSC-UHFFFAOYSA-N |
M.W : | 298.18 | Pubchem ID : | 16102683 |
Synonyms : |
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | 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 |
---|---|---|
76% | With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate; In 1,4-dioxane; at 95℃;Inert atmosphere; | Synthesis of AM362-A. To a degassed mixture of tert-butyl 5-bromoisoindoline-2- carboxylate (1 g, 3.3 mmol), <strong>[454482-11-2]1-methyl-1,2,3,6-tetrahydropyridine-4-boronic acid pinacol ester</strong> (1.12 g, 5.031 mmol ) and Cs2CO3 (3.2 g, 9.9 mmol ) in 1,4-dioxane (10 mL) was added Pd(dppf)Cl2 under N2 atmosphere and the mixture was heated at 95° C overnight. The reaction mixture was diluted with DCM (25 mL) and the catalyst was removed by filtration through the celite. The filtrate was concentrated in vacuo and the residue was purified by column chromatography on silica gel (PE:EtOAc = 80:20~60:40) to give AM362-A (0.8 g, 76percent) as a brown gum. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
420 mg | With (2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1 ‘-biphenyl)[2-(2’-amino-1,1‘-biphenyl)]palladium(II) methanesulfonate; caesium carbonate; In 1,4-dioxane; at 100℃; for 12.0h;Inert atmosphere; | To a solution of ferf-butyl 5-bromoisoindoline-2-carboxylate (compound 15a, 1.12 g, 3.75 mmol) in l,4-dioxane (10 mL) was added Ol-benzyl 02-methyl piperazine- l,2-dicarboxylate (CAS: 126937-43-7, Vendor: BePharm, 950 mg, 3.41 mmol), CS2CO3 (1.67 g, 5.12 mmol) and XPhos Pd G3 (289 mg, 0.34 mmol). The mixture was stirred at 100 C under N2 for 12 hrs. After being cooled down, the mixture was filtered and concentrated. The residue was diluted with EtOAc (10 mL) and washed with water (3 mL) and brine (3 mL), dried over anhydrous Na2S04, concentrated to give a cmde product which was purified by flash column (PE/EtOAc = 3/1) to give compound 15b (420 mg) as a yellow oil. MS: calc’d 496 (MH+), measured 496 (MH+). |
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