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CAS No. : | 1214336-88-5 | MDL No. : | MFCD14698110 |
Formula : | C7H5BrFNO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 234.02 g/mol | Pubchem ID : | - |
Synonyms : |
|
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 |
---|---|---|
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 19 h / 65 °C 2: Dess-Martin periodane / dichloromethane / 20 °C | ||
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 19 h / 65 °C 2: Dess-Martin periodane / dichloromethane / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 19 h / 65 °C 2.1: Dess-Martin periodane / dichloromethane / 20 °C 3.1: isopropylmagnesium chloride; lithium chloride / 2-methyltetrahydrofuran / 1 h / Cooling with ice 3.2: 20 °C | ||
Multi-step reaction with 3 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 19 h / 65 °C 2.1: Dess-Martin periodane / dichloromethane / 20 °C 3.1: TurboGrignard / 2-methyltetrahydrofuran / 1 h / Cooling with ice 3.2: 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate In N,N-dimethyl-formamide at 65℃; for 19h; | 8.1 Step 1: methyl 5-fluoro-6-(3-hydroxyazetidin-1-yl)nicotinate Step 1: methyl 5-fluoro-6-(3-hydroxyazetidin-1-yl)nicotinate (0261) A mixture of 102 azetidin-3-ol hydrochloride (2.8 g, 26 mmol), 103 methyl 6-bromo-5-fluoronicotinate (5.0 g, 21 mmol), and 23 potassium carbonate (7.4 g, 53 mmol) up in 8 DMF (100 mL) was heated at 65° C. for 19 hours. The mixture was purified by flash chromatography (silica gel) to provide the desired 104 product. LCMS-ESI+(m/z): [M+H]+ calcd for C10H12FN2O3: 227.1; found: 227.0. | |
With potassium carbonate In N,N-dimethyl-formamide at 65℃; for 19h; | 3.1 Step 1: methyl 5-fluoro-6-(3-hydroxyazetidin-1-yl)nicotinate (3a) Step 1: methyl 5-fluoro-6-(3-hydroxyazetidin-1-yl)nicotinate (3a) A mixture of azetidin-3-ol hydrochloride (2.8 g, 26 mmol), methyl 6-bromo-5-fluoronicotinate (5.0 g, 21 mmol), and potassium carbonate (7.4 g, 53 mmol) in DMF (100 mL) was heated at 65 °C for 19 hours. The mixture was purified by flash chromatography (silica gel) to provide the desired product. LCMS-ESI+ (m/z): [M+H]+ calcd for C10H12FN2O3: 227.1; found: 227.0. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 19 h / 65 °C 2.1: Dess-Martin periodane / dichloromethane / 20 °C 3.1: isopropylmagnesium chloride; lithium chloride / 2-methyltetrahydrofuran / 1 h / Cooling with ice 3.2: 20 °C 4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 °C | ||
Multi-step reaction with 4 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 19 h / 65 °C 2.1: Dess-Martin periodane / dichloromethane / 20 °C 3.1: TurboGrignard / 2-methyltetrahydrofuran / 1 h / Cooling with ice 3.2: 20 °C 4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 19 h / 65 °C 2.1: Dess-Martin periodane / dichloromethane / 20 °C 3.1: isopropylmagnesium chloride; lithium chloride / 2-methyltetrahydrofuran / 1 h / Cooling with ice 3.2: 20 °C 4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 °C 5.1: potassium carbonate; sodium iodide / N,N-dimethyl-formamide / 18 h / 60 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 19 h / 65 °C 2.1: Dess-Martin periodane / dichloromethane / 20 °C 3.1: isopropylmagnesium chloride; lithium chloride / 2-methyltetrahydrofuran / 1 h / Cooling with ice 3.2: 20 °C 4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 °C 5.1: potassium carbonate; sodium iodide / N,N-dimethyl-formamide / 18 h / 60 °C 6.1: lithium hydroxide monohydrate / tetrahydrofuran; water / 18 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 19 h / 65 °C 2.1: Dess-Martin periodane / dichloromethane / 20 °C 3.1: TurboGrignard / 2-methyltetrahydrofuran / 1 h / Cooling with ice 3.2: 20 °C 4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 °C 5.1: potassium carbonate; sodium iodide / N,N-dimethyl-formamide / 65 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 19 h / 65 °C 2.1: Dess-Martin periodane / dichloromethane / 20 °C 3.1: TurboGrignard / 2-methyltetrahydrofuran / 1 h / Cooling with ice 3.2: 20 °C 4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 °C 5.1: potassium carbonate; sodium iodide / N,N-dimethyl-formamide / 65 °C 6.1: lithium hydroxide monohydrate / tetrahydrofuran; water / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane at 110℃; for 18h; Inert atmosphere; Sealed tube; | 3.1 Step 1: Methyl 5-fluoro-6-methylnicotinate The commercially available methyl 6-bromo 5-fluoronicotinate (360 mg, 1.54 mmol) was mixed with trimethyl-1,3,5,2,4,6-trioxatriborinane (966 mg, 7.69 mmol), K2CO3 (319 mg, 2.31 mmol), and Pd(Ph3P)4 (196 mg, 0.169 mmol) in 1,4-dioxane (5 mL). The mixture was sparged with N2 and stirred at 110 o C in a sealed tube under N2 atmosphere for 18 h. After cooled, the reaction was added ethyl acetate and washed with water. The organic layer was dried (Na2SO4) and filtered through Celite. Solvent was evaporated and the resulting residue was purified by chromatography (Silica gel, hexane/ethyl acetate, 1:0 to 1:1) to afford the title compound, 198 mg (76%). LC-MS: m/z [M+H]+ 170.1 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate In 1-Methylnaphthalene at 120℃; for 18h; Inert atmosphere; | 8.1 Step 1: Methyl 6-((2.3-dihydro-1H-inden-2-yl)amino-5-fluoronicotinate General procedure: To a solution of methyl 5-fluoro-6-bromonicotinate (100 mg, 0.47 mmol) in NMP (2 mL) was added 2,3-dihydro-1H-inden-2-amine (62.6 mg, 0.47 mmol) and K2CO3 (195 mg, 1.41 mmol) in a vial. The reaction mixture was stirred and heated at 120 o C under N2 for 18 h. After cooled and diluted with ethyl acetate, the organic layer was washed with water. Dried (Na2SO4), filtered and concentrated, the resulting residue was purified by chromatography (Silica gel, hexane/ethyl acetate, 1:0 to 0:1) to afford the title compound as a brown oil, 38 mg (31%). LC- MS: m/z [M+H]+ 287.3 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / 1,4-dioxane / 18 h / 110 °C / Inert atmosphere; Sealed tube 2: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 48 h / 75 °C |
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