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Chemical Structure| 442562-83-6 Chemical Structure| 442562-83-6

Structure of 442562-83-6

Chemical Structure| 442562-83-6

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Product Details of [ 442562-83-6 ]

CAS No. :442562-83-6
Formula : C14H9F2N
M.W : 229.22
SMILES Code : FC1=C(F)C(C2=CC=CC3=C2C=CN3)=CC=C1
MDL No. :MFCD18404324

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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.

  • Downstream synthetic route of [ 442562-83-6 ]

[ 442562-83-6 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 38573-88-5 ]
  • [ 388116-27-6 ]
  • [ 442562-83-6 ]
YieldReaction ConditionsOperation in experiment
70% With sodium hydroxide;tetrakis(triphenylphosphine) palladium(0); In tetrahydrofuran; at 70℃;Inert atmosphere; Step 2 4-(2,3-Difluoro-phenyl)-1H-indole 4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-indole 6b (1.22 g, 5 mmol) was dissolved in 20 ml of tetrahydrofuran under stirring, and added with <strong>[38573-88-5]1-bromo-2,3-difluoro-benzene</strong> (0.97 g, 5 mmol), tetrakis (triphenylphosphine)palladium (0.17 g, 0.15 mmol) and sodium hydroxide solution (7 ml, 2 mol/L) under an argon atmosphere. Upon completion of the addition, the reaction system was stirred at 75° C. in an oil bath overnight. After thin lay chromatography showed the disappearance of starting materials, the reaction mixture was naturally cooled down to room temperature and extracted with ethyl acetate (20 ml*3). The combined organic extracts were washed with saturated brine (10 ml), dried over anhydrous sodium sulfate, filtered to remove the drying agent and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain 4-(2,3-difluoro-phenyl)-1H-indole 6c (800 mg, yield 70percent) as a white solid. MS m/z (ESI): 228.4 [M-1]
70% With sodium hydroxide;tetrakis(triphenylphosphine) palladium(0); In tetrahydrofuran; at 75℃;Inert atmosphere; 4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-indole 6b (1.22 g, 5 mmol) was dissolved in 20 ml of tetrahydrofuran under stirring, and added with <strong>[38573-88-5]1-bromo-2,3-difluoro-benzene</strong> (0.97 g, 5 mmol), tetrakis (triphenylphosphine)palladium (0.17 g, 0.15 mmol) and sodium hydroxide solution (7 ml, 2 mol/L) under an argon atmosphere. Upon completion of the addition, the reaction system was stirred at 75°C in an oil bath overnight. After thin lay chromatography showed the disappearance of starting materials, the reaction mixture was naturally cooled down to room temperature and extracted with ethyl acetate (20 ml.x.3). The combined organic extracts were washed with saturated brine (10 ml), dried over anhydrous sodium sulfate, filtered to remove the drying agent and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain 4-(2,3-difluoro-phenyl)-1H-indole 6c (800 mg, yield 70percent) as a white solid. MS m/z (ESI): 228.4[M-1]
70% With sodium hydroxide;tetrakis(triphenylphosphine) palladium(0); In tetrahydrofuran; at 75℃;Inert atmosphere; 4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-indole 3b (1.22 g, 5 mmol) was dissolved in 20 mL of tetrahydrofuran under stirring under an argon atmosphere, and <strong>[38573-88-5]1-bromo-2,3-difluoro-benzene</strong> (0.97 g, 5 mmol), tetrakis (triphenylphosphine) palladium (0.17 g, 0.15 mmol) and 7 mL of sodium hydroxide solution (2M) were then added to the solution. Upon completion of the addition, the reaction system was stirred at 75°C in an oil bath overnight. The reaction was completed until TLC showed the disappearance of starting materials. The reaction mixture was naturally cooled down to room temperature and extracted with ethyl acetate (20 mL*3). The combined organic extracts were washed with saturated brine (10 mL), dried over anhydrous sodium sulfate, filtered to remove the drying agent and concentrated under reduced pressure. The resulting solid was purified by silica gel column chromatography to give the title compound 4-(2,3-difluoro-phenyl)-1H-indole 3c (800 mg, yield 70percent) as a white solid. MS m/z (ESI): 228.4[M-1]
70% With sodium hydroxide;tetrakis(triphenylphosphine) palladium(0); In tetrahydrofuran; water; at 75℃;Inert atmosphere; Step 2 4-(2,3-difluoro-phenyl)-1H-indole 4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-indole 3b (1.22 g, 5 mmol) was dissolved in 20 mL of tetrahydrofuran under stirring under an argon atmosphere, and <strong>[38573-88-5]1-bromo-2,3-difluoro-benzene</strong> (0.97 g, 5 mmol), tetrakis (triphenylphosphine) palladium (0.17 g, 0.15 mmol) and 7 mL of sodium hydroxide solution (2M) were then added to the solution. Upon completion of the addition, the reaction system was stirred at 75° C. in an oil bath overnight. The reaction was completed until TLC showed the disappearance of starting materials. The reaction mixture was naturally cooled down to room temperature and extracted with ethyl acetate (20 mL*3). The combined organic extracts were washed with saturated brine (10 mL), dried over anhydrous sodium sulfate, filtered to remove the drying agent and concentrated under reduced pressure. The resulting solid was purified by silica gel column chromatography to give the title compound 4-(2,3-difluoro-phenyl)-1H-indole 3c (800 mg, yield 70percent) as a white solid. MS m/z (ESI): 228.4[M-1]
2.92 g (82%) With nitrogen;Pd(PPh3)4; palladium; In tetrahydrofuran; water; ethyl acetate; Example A-26 4-(2,3-Difluoro-phenyl)-1H-indole To a mixture of 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-indole (3.78 g, 15.5 mmol), and <strong>[38573-88-5]1-<strong>[38573-88-5]bromo-2,3-difluorobenzene</strong></strong> (3 g, 15.5 mmol) in THF (55 mL) were added Palladium catalyst Pd(PPh3)4 (0.54 g, 0.47 mmol) and the freshly prepared sodium hydroxide solution (1.865 g, 47 mmol in 22 mL of water). The system was degassed and then charged with nitrogen. The degas procedure was repeated for three times. The mixture was stirred under nitrogen at 75° C. oil bath for overnight. TLC showed the completion of the coupling reaction. The mixture was cooled to room temperature, diluted with ethyl acetate, and separated from water layer. The ethyl acetate solution was washed with brine, and dried over Na2SO4. After filtration, the solvents were evaporated, and the crude product was purified by a silica gel column to give 2.92 g (82percent) of 4-(2,3-difluoro-phenyl)-1H-indole.

 

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