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CAS No. : | 1045809-78-6 | MDL No. : | MFCD08061126 |
Formula : | C9H14BNO2S | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | UPECZVDBUMIIIL-UHFFFAOYSA-N |
M.W : | 211.09 | Pubchem ID : | 16761714 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H332-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 |
---|---|---|
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; caesium carbonate; In 1,4-dioxane; at 110℃; for 2.0h;Inert atmosphere; | A suspension of 100 mg (0.19 mmol) of 2-[(3R)-3-methylmorpholin-4-yl]-8-[1-(tetrahydro-2H- pyran-2-yl)-1H-pyrazol-5-yl]-1,7-naphthyridin-4-yl trifluoromethanesulfonate, 80 mg (0.38 mmol) <strong>[1045809-78-6]5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2-thiazole</strong>, 15 mg (0.019 mmol) of [1,1?-bis(diphenylphosphino)ferrocene]dichloropalladium(II) complex with dichloromethane (1:1, Pd(dppf)C12) and 247 mg (0.76 mmol) of ceasium carbonate in 1.3 ml of dioxane was degased with argon. Under argon, the reaction mixture was stirred at 110C for 2 hours. After cooling the reaction mixture was diluted with saturated aqueous sodium chloride solution and extracted with ethyl acetate (2x). The combinded organic phases were filtered using a Whatman filter and thenconcentrated to give the crude product that was used without further purification in the next step. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
26% | With potassium phosphate; methanesulfonic acid(2-dicyclohexylphosphino-2?,4?,6?-triisopropyl-1,1?-biphenyl)[2-(2?-amino-1,1?-biphenyl)]palladium(II); In 1,4-dioxane; water; at 80 - 110℃;Inert atmosphere; | To a suspension of tert-butyl 4-{3-bromo-5-[(4-methoxybenzyl)oxy]pyrazolo[l,5-a]pyrimidin-7- yl}piperidine-l-carboxylate (100 mg, 193 muiotaetaomicron) in 1,4-dioxan (4.0 ml) were added 5-(4,4,5,5- tetramethyl-l,3,2-dioxaborolan-2-yl)-l,2-thiazole (81.6 mg, 387 muiotaetaomicron), tripotassium phosphate (970 mu, 1.0 M in water, 970 muiotaetaomicron) and XPhos Pd G3 (4.09 mg, 4.83 muiotaetaomicron). The mixture was degased with argon for 2 min and stirred overnight at 110 C. A new portion of 5-(4,4,5,5-tetramethyl-l,3,2- dioxaborolan-2-yl)-l,2-thiazole (81.6 mg, 387 muiotaetaomicron) and XPhos Pd G3 (4.09 mg, 4.83 muiotaetaomicron) was added and the mixture was stirred for 2 h at 110 C. A last portion of 5-(4,4,5,5-tetramethyl-l,3,2- dioxaborolan-2-yl)-l,2-thiazole (81.6 mg, 387 muiotaetaomicron) and XPhos Pd G3 (4.09 mg, 4.83 muiotaetaomicron) was added and the mixture was stirred overnight at 80 C and 1 h more at 110 C. After cooling to room temperature, the mixture was purified by preparative HPLC (gradient acetonitrile/water with 0.1 % formic acid). Evaporation of the combined product fractions yielded the title compound. The obtained amount was 26.0 mg (100 % purity, 26 % of theory). LC-MS (Method 8B): Rt = 1.67 min; MS (ESIpos): m z = 522 [M+H]+ |
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4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)isothiazole
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