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CAS No. : | 399-96-2 | MDL No. : | MFCD00671760 |
Formula : | C6H6FNO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | MXJQJURZHQZLNN-UHFFFAOYSA-N |
M.W : | 127.12 | Pubchem ID : | 2735918 |
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 |
---|---|---|
To the solution of 4-amino-2-fluorophenol (41 mg, 0.32 mmol) in dried DMF (3 mL), was added NaH (13 mg, 0.54 mmol). The mixture was stirred at 0 °C for 10 min, and then a solution of 4-chloro-5-(4-fluorophenyl)thieno[2,3-d]pyrimidine 4i (50 mg, 0.19 mmol) in dried DMF (1 mL) was added. The mixture was stirred at 0 °C for 1.5 h. Ice water (5 mL) was added to quench the reaction and the mixture was extracted by Et2O (3 .x. 10 mL). The organic layer was washed with brine, dried over Na2SO4, and concentrated under reduced pressure to obtain the crude product, which was purified by silica gel column chromatograph. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
36.5% | With toluene-4-sulfonic acid; In N,N-dimethyl-formamide; toluene; at 120℃; for 3h;microwave irradiation; | A mixture of 4-amino-2-fluorophenol (509 mg, 4.00 mmol), N-formylformohydrazide(426 mg, 4.84 mmol), and /?-toluenesulfonic acid (826 mg, 4.34 mmol) in toluene (15 mL) and DMF (1.5 mL) was heated under microwave irradiation at 120 °C for 3 h. The mixture was concentrated and the residue was partitioned between DCM and water. The organic phases were combined, dried over MgS04, filtered, and concentrated. The residue was purified by column chromatography (Si02, hexane/EtOAc gradient and then EtOAc/MeOH 10: 1) to give the title compound as a tan solid (262 mg, 36.5percent). Exact mass calculated for C8H6FN30: 179.05, found: LCMS mlz = 180.2 [M+H]+; lU NMR (400 MHz, DMSO- ) delta ppm 7.06-7.10 (m, 1H), 7.32- 7.35(m, 1H), 7.62-7.66 (m, 1H), 8.98 (s, 2H). 10.2 (s, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
56% | With sodium carbonate; sodium hydroxide; In tetrahydrofuran; 1,4-dioxane; water; at 80℃; | General procedure: P-aminophenol or 2-fluoro-4-aminphenol 18a-b (0.1 mol)whichwas dissolved in tetrahydrofuran (50 ml),was added to a 1,4-dioxane/H2O(50 ml, 5:1) solution of compounds 17a-b or 20a-b,sodium carbonate and hydrogen sodium at 80 C for 2 h. Then thesolution was concentrated in vacuum and washed with water,filtered to give a solid. |