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CAS No. : | 13195-50-1 | MDL No. : | MFCD00022493 |
Formula : | C4H2BrNO2S | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | ZPNFMDYBAQDFDY-UHFFFAOYSA-N |
M.W : | 208.03 | Pubchem ID : | 83222 |
Synonyms : |
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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: |
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* 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 potassium acetate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In N,N-dimethyl-formamide; at 20 - 60℃; for 2h; | A solution of compound 52ii (100 mg, 0.48 mmol), 52iii (73 mg, 0.48 mmol), and KOAc (190 mg, 1.92 mmol) in DMF (5 ml) was degassed thrice and PdCl2(drhopf) (36 mg, 0.048 mmol) added to it at rt under an argon atmosphere. The reaction mixture was heated at 6O0C for two hours, diluted with ethyl acetate (EA) and washed with brine. The organic layer was dried, concentrated, and the residue separated by column chromatography on silica gel employing as eluent EA/Hex (0 - 80percent) to yield 52i. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; copper(l) iodide; In N,N-dimethyl-formamide; at 20 - 60℃; for 2h; | A solution of compound 59ii (200 mg, 0.96 mmol) and 59iii (127 mg, 0.96 mmol) in DMF (3 ml) was degassed thrice and PdCl2(dppf) (50 mg, 0.07 mmol) was added to it, EPO <DP n="135"/>followed by CuI (8.5 mg, 0.043 mmol) and TEA (0.27 ml, 1.92 mmol), at rt, under argon atmosphere and the reaction mixture was heated at 60 0C for two hours. The reaction mixture was diluted with EA, washed with brine, the organic layer separated, dried, and concentrated to yield a residue which was separated by column chromatography on silica gel employing as eluent EA\\Hex (0-70percent) to yield compound 5Si. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium fluoride;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; ethanol; water; toluene; at 90℃; | Example 6B methyl flJR,2i')-2-f4-(5-ni<tauothien-2-yl')benzoyl]cvclopentanecarboxylate To an ambient slupiy of 6A (270 rng, 0.75 mmol), 2-brorno-5-nittauo-thiophene (156 mg, 0.75 mmol) and potassium fluoride (130 mg, 2,24 mmol) in dimethyoxyethane/toluene/ethanol/HiO (10/1/6/3 ratio, 3 mL) was added palladium tettauakis(triphenylphosphipie) (10 mg, 0 0086 mmol) in a single portion The reaction was heated at 90 0C overnight, cooled Io room iemperatipie, filtered through celite, washed with ethyl acetate, concent. aled and puiified by flash chromatography on SiO? column (0 - 5percent ethyl acetate in hexanes) to provide the title compound as yellow solid 1H NMR (500 MHz, DMSO-d6) delta ppm 1 .54-1 87 (m, 4H), 1 99-2 20 (m, 2H), 3 30 (m, IH), 3.57 (s, 3H), 4. 12 (m, 1 H), 7 ,84 (d, ./ = 4.27 Hz, 1 H), 8 ,01 (d, J = 8.54 Hz, 2H), 8 10 (d, J = 8 54 Hz, 2H), 8 23 (d, J = 427 Hz, IH); MS (DCl/NHj) m/z 360 [M+I-lf |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
11% | With caesium carbonate;palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In 1,4-dioxane; water; at 100℃; for 6h; | A mixture of potassium methoxymethyl trifluoroborate (33 mg, 0.22 mmol), <strong>[13195-50-1]2-bromo-5-nitrothiophene</strong> (30 mg, 0.14 mmol), 1,4-dioxane (1.5 ml), water (0.15 ml), cesium carbonate (235 mg, 0.72 mmol) , palladium (II) acetate (3.2 mg, 0.014 mmol), and 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (9.0mg, 0.014 mmol) was stirred at 100C (external temperature) for 6 hours. After the reaction mixture was cooled at room temperature, water and ethyl acetate were added to the mixture, followed by filtration using Celite. The organic layer was washed with an aqueous saturated sodium chloride solution, and the solvent was distilled off under reduced pressure. The residue was purified by NH silica gel column chromatography (heptane:ethyl acetate=3:1) to obtain the title compound (2.7 mg, 0.016 mmol, 11%). 1H-NMR Spectrum (CD3OD) delta (ppm): 3.43 (3H, s), 4.65 (2H, d, J=0.9 Hz), 7.04 (1H, dt, J=4.2, 0.9 Hz), 7.89(1H, d, J=4.2 Hz). |
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