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CAS No. : | 875781-43-4 | MDL No. : | MFCD09834822 |
Formula : | C6H4BrN3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | KTKMLXBEBKGQGL-UHFFFAOYSA-N |
M.W : | 198.02 | Pubchem ID : | 25067308 |
Synonyms : |
|
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 |
---|---|---|
97% | A solution of 2-bromo-5H-pyrrolo[2,3-b]pyrazine (78.0 g, 394 mmol, Ark Pharm) in anhydrous DMF (272 mL) was added drop-wise over about 60 min to a stirred suspension of NaH (12.8 g, 532 mmol) in anhydrous DMF (543 mL) at about 0-5 C. The brown reaction solution was stirred for about 30 min at about 0-5 C. then a solution of p-toluenesulfonyl chloride (94.0 g, 492 mmol) in anhydrous DMF (272 mL) was added drop-wise over about 60 min at about 0-5 C. The reaction mixture was stirred at about 0-5 C. for about 1 h then allowed to warm to ambient temperature and stirred for about 18 h at ambient temperature. The reaction mixture was poured slowly into ice water (6 L), followed by the addition of aqueous 2.5 N NaOH (50.0 mL, 125 mmol). The precipitate was collected by filtration and stirred with cold water (3×200 mL). The solid was collected by filtration and dried to constant weight in a vacuum oven at about 55 C. to yield 2-bromo-5-tosyl-5H-pyrrolo[2,3-b]pyrazine (134.6 g, 97%) as a pale beige solid: LC/MS (Table 2, Method d) Rt=1.58 min; MS m/z: 352/354 (M+H)+. | |
86% | With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 30℃; for 8h;Inert atmosphere; | Under the protection of nitrogen content 60% of NaH 12 mmol suspended in DMF 30 ml in, adding dissolved in 10 ml DMF of the B - 110 37.4 mmol, reaction 1 h after, adding dissolved in 20 ml DMF to toluene sulfonyl chloride 12 mmol, 30 C reaction 8 h after, the reaction mixture of ethyl acetate extraction 2 time, the combined ethyl acetate after drying, after recovering ethyl acetate, petroleum ether ethyl acetate column chromatography (5:1), the obtained product is 3.0 g, yield 86% |
79.3% | With sodium hydride; In tetrahydrofuran; mineral oil; at -15 - 20℃; for 1h; | 2-bromo-5H-pyrrolo [2,3-b] pyrazine (10 g, 50.5 mmol)Of tetrahydrofuran (150 mL)Was added sodium hydride (60%, 3.1 g, 78 mmol)The mixture was stirred at room temperature for 1 hour,P-toluenesulfonyl chloride (12.6 g, 65.4 mmol) was added under ice-Continue to stir at room temperature,Diluted with water (100 mL)Dichloromethane extraction (100 mL x 3),Dried over anhydrous sodium sulfate,Concentrated column chromatography (petroleum ether / ethyl acetate (v / v) = 8/1)To give 14.1 g of a pale yellow flocculent solid in a yield of 79.3%. |
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