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CAS No. : | 380430-57-9 | MDL No. : | MFCD02179473 |
Formula : | C7H10BNO4S | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | NDVJJEADFLTFCD-UHFFFAOYSA-N |
M.W : | 215.04 | Pubchem ID : | 2773537 |
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 |
---|---|---|
With sodium hydrogencarbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; water; toluene; for 4.5h;Heating / reflux; | To toluene 24mL solution of tert-butyl 4-bromo-2-nitrobenzoate 3.0g were added ethanol 9.0mL, water 4.5mL, 4-N-(methanesulfonamide)phenylboronic acid 2.6g, sodium hydrogen carbonate 2.1g and tetrakis(triphenylphosphine)palladium(0) 0.57g, and it was heated and refluxed under nitrogen atmosphere for 4 hours and 30 minutes. After the reaction mixture was cooled to room temperature, ethyl acetate and water were added to it. After insoluble matter was filtrated, the organic layer was separated and collected, dried over anhydrous magnesium sulfate after washing with saturated sodium chloride aqueous solution, and the solvent was removed under reduced pressure. Hexane and diisopropyl ether were added to the obtained residue, solid matter was filtrated to give tert-butyl 4-(4-N-(methanesulfonamido)phenyl)-2-nitrobenzoate 3.9g of white solid. 1H-NMR(DMSO-d6) delta value: 1.51(9H,s),3.06(3H,s),7.32-7.37(2H,m),7.79-7.84(2H,m),7.89(1H,d,J=8.2Hz),8.07(1H,dd,J=8.2,1.8Hz),8 .23(1H,d,J=1.8Hz),10.02-10.08(1H,broad). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
3% | With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; ethanol; water; at 80℃; | Synthesis of N-[4-(4-Amino-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidin-3-yl)-phenyl]-methanesulfonamide (BA40); A solution of 4-Methanesulfonylaminophenylboronic acid (24 mg, 0.11 mmol) in EtOH (3.3 ml) was added to a solution of 3-iodo-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine (30 mg, 0.10 mmol) in DME (12 ml). Pd(PPh3)4 (30 mg, 0.03 mmol) and saturated Na2CO3 (1.9 ml) were added and the reaction was heated to 80 C. under an argon atmosphere overnight. After cooling, the reaction was extracted with saturated NaCl and CH2Cl2. Organic phases were combined, concentrated in vacuo and purified by RP-HPLC (MeCN:H2O:0.1% TFA) to yield BA40 (0.9 mg, 3% yield). ESI-MS (M+H)+ m/z calcd 347.1, found 347.0. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium carbonate;bis-triphenylphosphine-palladium(II) chloride; In 1,2-dimethoxyethane; water; for 1h;Heating / reflux; | To a mixture of 3-iodo-7-({4-methyl-2-[4-(trifluoromethyl)phenyl](1,3-thiazol-5-yl)}methoxy)chromen-4-one (55.0 mg, 0.10 mmol), 4-(dihydroxyboron)-(methylsulfonyl)phenylamine (22.5 mg, 0. 15 mmol), bis-(triphenylphosphine) palladium (II) dichloride(3.5 mg, 0.005 mmol) was added dimethoxyethane (2 ml) and aqueous sodium carbonate solution (2M, 0.1 ml, 2 equivs). The mixture was refluxed for 1 hour, cooled to ambient temperature, filtered through celite (3 g), and the celite washed with ethyl acetate (50 ml). The filtrate was washed with brine (30 ml), and dried over sodium sulfate. The solvent was removed under reduced pressure, and the residue chromatographed on silica gel, eluting with ethyl acetate/hexanes 50/1, after which the product was crystallized from ethyl acetate (3 ml), to provide 3-{4-[(methylsulfonyl)amino]phenyl}-7-({2-[4-(trifluoromethyl)phenyl](1,3-thiazol-5-yl)}methoxy)chromen-4-one. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium carbonate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; water; at 180℃; for 0.05h;Microwave irradiation; | 1,1 -Dimethylethyl (4-bromo-1/-/-pyrrolo[2,3-o]pyridin-2-yl)acetate (0.311g, 1mmol), {4- [(methylsulfonyl)amino]phenyl}boronic acid (0.32Og, 1.5mmol), sodium carbonate (0.09Og) and bis(diphenylphosphino)ferrocene palladium (II) chloride (0.026g) were mixed in dioxan/water (5:1, 3ml). The mixture was heated in the Biotage Initiator mw at 18O0C for 3 mins. The mixture was separated between DCM (50ml) and water (10ml). The organic phase was evaporated and purified by silica SPE cartridge eluting with EtOAc/DCM (0- 50%) over an hour. The main fraction was evaporated to give the title compound as a mustard coloured crystalline solid (0.301 g). MH+402, rt= 3.0 mins |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium carbonate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; water; at 180℃; for 0.05h;Microwave irradiation; | 2-(4-Bromo-1 H-pyrrolo[2,3-b]pyridin-2-yl)-lambda/-methylacetamide (0.14mmol), {4-[(methylsulfonyl)amino]phenyl}boronic add (0.045g, 0.21 mmol), sodium carbonate (0.014g) and bis(diphenylphosphino)ferr?cene palladium (II) chloride (0.004g) were treated with dioxan/water (5:1 , 1ml). The mixture was heated in the Biotage Initiator mw at 180 0C for 3 mins. The reaction was diluted with DCM (15ml) and washed with water (5ml). The organic phase was evaporated and purified by MDAP. The main peak was evaporated to give the title compound as a cream solid (0.005g). MH+359, rt= 2.26 mins |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium carbonate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; water; at 180℃; for 0.05h;Microwave irradiation; | 2-(4-Bromo-1/-/-pyrrolo[2,3-/3]pyridin-2-yl)-lambda/,lambda/-dimethylacetamide (0.14mmol), {4- [(methylsulfonyl)amino]phenyl}boronic acid (0.045g, 0.21 mmol), sodium carbonate (0.014g) and bis(diphenylphosphino)ferrocene palladium (II) chloride (0.004g) were treated with dioxan/water (5:1 , 1ml). The mixture was heated in the Biotage Initiator mw at 180 0C for 3 mins. The reaction was diluted with DCM (15ml) and washed with water <n="178"/>(5ml). The organic phase was evaporated and purified by MDAP. The main peak was evaporated to give the title compound as a brown gum (0.014g). MH+373, rt= 2.33 mins |