4-Fluoro-1,3-phenylenediamine

In Example 1, the m-nitroacetophenone used was replaced with equimolar 4-fluoro-3-nitroaniline, the reaction was carried out at 80 °C for 48 hours at 4.0 MPa. The other procedure was the same as in to give 4-fluoro-1, 3-diaminobenzene in a yield of 94percent, _: A solution of 16.44 mg (0.04 mmol) 4, 4'-dimethoxy-2, 2'-bipyridine silver 11.22 mg (0.1 mmol) of potassuim t-butoxide and 1 mL of 1, 4-dioxane were charged into an autoclave. After stirring, 165.15 mg (1 mmol) of m-nitroacetophenone was added and the mixture was stirred at 80 °C. The reaction was carried out for 8 hours. After the reaction has finishedm the reaction solution was extracted with water and dichloromethane to collect the organic phase. Then, the organic phase was dried over anhydrous NaGeneral procedure: Before each run, the system (see Fig.4) was allowed to equilibrate by pumping solvent through for 30min with the Tube-in-Tube device at 16bar of hydrogen. An omnifit cartridge (20.0mm OD, 15.0mm ID) containing 1g of Pd-C catalyst was used. To avoid an overpressure of the system in the event of blockage, the upper pressure cut-off limit on the Knauer pump was set to 25bar. With the injection loop disconnected from the flow line, the loop was opened and filled manually (using a syringe) with 3.6mL of a 0.076M solution of starting material in ethanol (excess starting material solution exiting the loop was recovered for reuse). The injection loop was then closed off and switched into the flow stream. The outlet from the system (downstream of the back-pressure regulator) was collected for 120min. The solvent was removed under reduced pressure (using a rotary evaporator followed by a 2-stage rotary vane pump) to afford the product.In a nitrogen-atmosphere, 5 ml of glacial acetic acid and 0.5 ml of water were mixed to prepare a 20 ml round-bottomed flask. To the flask was added 2, 4-dinitro-1-fluorobenzene (1 mmol) was dispersed. 670 mg of iron powder (100 mesh) was added slowly for 10 minutes while vigorously stirring the high temperature was maintained at 25 °C . After reacting for 6 hours, it was diluted with 15 ml of ethyl acetate (EtOAc)Lt; / RTI & gt; After filtration, it was thoroughly washed with water and 10percent NaHCO3 solution and dried in a vacuum oven. Stationary phaseAs eluent and neutral aluminum and purification by chromatography using a solution of 4percent EtOAc in hexane to give the target compound. Yield: 82percent.4-Bromo-6-methyl-1H-indole-2-carboxylic acid ethyl ester (90 mg, 0.25 mmol) and Pd / C (45 mg) were dissolved in THF (5 mL), and the hydrogenation reaction was catalyzed at room temperature for 8 hours. The reaction was complete. The diatomaceous earth was filtered to remove Pd / C, and the filtrate was concentrated and ether was added to recrystallize to obtain 60 mg of a white solid with a yield of 72.8% and a melting point of 151-152 C.General procedure: Before each run, the system (see Fig.4) was allowed to equilibrate by pumping solvent through for 30min with the Tube-in-Tube device at 16bar of hydrogen. An omnifit cartridge (20.0mm OD, 15.0mm ID) containing 1g of Pd-C catalyst was used. To avoid an overpressure of the system in the event of blockage, the upper pressure cut-off limit on the Knauer pump was set to 25bar. With the injection loop disconnected from the flow line, the loop was opened and filled manually (using a syringe) with 3.6mL of a 0.076M solution of starting material in ethanol (excess starting material solution exiting the loop was recovered for reuse). The injection loop was then closed off and switched into the flow stream. The outlet from the system (downstream of the back-pressure regulator) was collected for 120min. The solvent was removed under reduced pressure (using a rotary evaporator followed by a 2-stage rotary vane pump) to afford the product.In a nitrogen-atmosphere, 5 ml of glacial acetic acid and 0.5 ml of water were mixed to prepare a 20 ml round-bottomed flask. To the flask was added 2, 4-dinitro-1-fluorobenzene (1 mmol) was dispersed. 670 mg of iron powder (100 mesh) was added slowly for 10 minutes while vigorously stirring the high temperature was maintained at 25 C . After reacting for 6 hours, it was diluted with 15 ml of ethyl acetate (EtOAc)Lt; / RTI & gt; After filtration, it was thoroughly washed with water and 10% NaHCO3 solution and dried in a vacuum oven. Stationary phaseAs eluent and neutral aluminum and purification by chromatography using a solution of 4% EtOAc in hexane to give the target compound. Yield: 82%.

Molecular Weight:126.13
XLogP3:0.8
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:3
Exact Mass:126.05932639
Monoisotopic Mass:126.05932639
Topological Polar Surface Area:52
Heavy Atom Count:9
Complexity:97.1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes