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CAS No. : | 486422-05-3 | MDL No. : | MFCD07368237 |
Formula : | C14H22BNO4S | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | YFEWVSRTWWHXFP-UHFFFAOYSA-N |
M.W : | 311.20 | Pubchem ID : | 16414207 |
Synonyms : |
|
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 |
---|---|---|
57% | With water; sodium hydrogencarbonate;tetrakis(triphenylphosphine) palladium(0); In N,N-dimethyl-formamide; at 100.0℃; for 15.0h; | To a solution of Compound 1 (lOOmg, 0.228mmol) and 3-(4,4,5,5-tetramethyl- l,3,2-dioxaborolan-2-yl)-N,N-dimethylbenzenesulfonamide (106mg, 0.34mmol) in DMF (3mL) were added 2M aq. NaHCO3 (350μL) and Pd[PPh3J4 (26mg, 0.02mmol). The reaction was heated at 10O 0C for 15 h, allowed to cool, and then diluted with water (2OmL). The resultant precipitate was collected by filtration and air-dried. The crude product was re-dissolved in hot methanol/DMF, filtered hot, and then sufficient water was added to cause the solution to become cloudy. After cooling to room temperature and then further in an ice-bath, the solid was collected by filtration, washed with water and air-dried, followed by further drying under reduced pressure. This provided Compound 12 as a yellow/brown solid (65mg, 57%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
30% | With potassium phosphate; palladium diacetate; catacxium A; In butan-1-ol; at 50.0℃; for 16.0h;Inert atmosphere; | A solution of 8-iodo-N-[(l S)-2-methoxy-l-methyl-ethyl]-5-tetrahydropyran-4-yloxy- pyrido [4,3-d]pyrimidin-2-amine (100 mg, 225 umol, 1 eq), N,N-dimethyl-3-(4,4,5,5- tetramethyl-l,3,2-dioxaborolan-2-yl)benzenesulfonamide (106 mg, crude), K3PO4 (143 mg, 675 umol, 3 eq), Pd(OAc)2 (5 mg, 23 umol, 0.1 eq) and bis(l-adamantyl)-butylphosphane (8 mg, 23 umol, 0.1 eq) in n-BuOH (2 mL) was degassed and purged with N2 3 times, and then the mixture was stirred at 50 C for 16 hours under N2 atmosphere. On completion, the mixture was diluted with ethyl acetate (20 mL) and water (30 mL). The mixture was extracted with ethyl acetate (2 x 30 mL). The combined organic layer was washed with water (30 mL) and brine (2 x 30 mL), dried over Na2S04 and concentrated in vacuo. The residue was purified by prep-HPLC. The eluent was concentrated to remove organic solvent, and the aqueous solution was lyophilized to give the title compound (33.6 mg, 30% yield) as a white solid. The title compound was confirmed by 1H NMR and LCMS. |
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