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CAS No. : | 1211331-43-9 | MDL No. : | MFCD12827553 |
Formula : | C5H2BrF2N | Boiling Point : | 162.7±35.0°C at 760 mmHg |
Linear Structure Formula : | - | InChI Key : | N/A |
M.W : | 193.98 | Pubchem ID : | - |
Synonyms : |
|
TPSA :Topological Polar Surface Area | - | H-Bond Acceptor Count : | - |
XLogP3 : | - | H-Bond Donor Count : | - |
SP3 : | - | Rotatable Bond Count : | - |
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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Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | NaN02 (1.4 g, 14.4 mmol) was added in portions to a solution of 3-bromo-5- fluoro-pyridin-2-ylamine (5.2 g, 17.3 mmol) in a HF/pyridine mixture (40 mL) in a polyethylene reaction vessel. The resulting mixture was stirred at 0 C for 0.5 h, then heated to 50 C and stirred for 1 h. The reaction mixture was poured onto crushed ice, partially neutralized with Na2C03, and extracted with EtOAc. The organic phase was washed with brine, dried over Na2S04, filtered and concentrated to give the product (4.1 g, 68%) as a white solid. | |
42% | (8a) 3-Bromo-2,5-difluoropyridine Sodium nitrite (1.97 g, 28.6 mmol) was added in small portions to a solution of <strong>[869557-43-7]3-bromo-5-fluoropyridin-2-amine</strong> (WO20062578 A1, 3.64 g, 19.1 mmol) in hydrofluoric acid pyridine (10 mL) at -10C. After stirring at room temperature for two hours, water (100 mL) and sodium bicarbonate were added to the reaction mixture at 0C, followed by extraction with ethyl acetate (100 mL). Then, the organic layer was washed with water (100 mL) twice and dried over anhydrous sodium sulfate. After concentration under reduced pressure, the residue was purified by silica gel chromatography (methylene chloride) to obtain the title compound (1.56 g, 42%) as a brown liquid. 1H-NMR (400 MHz, CDCl3): delta ppm: 7.78 (1H, dt, J = 2.7, 6.7 Hz), 8.02 (1H, dd, J = 1.6, 2.4 Hz). | |
42% | With pyridine hydrogenfluoride; sodium nitrite; at -10 - 20℃; for 2h; | Sodium nitrite (1.97 g, 28.6 mmol) was added in small portions to a solution of <strong>[869557-43-7]3-bromo-5-fluoropyridin-2-amine</strong> (, 3.64 g, 19.1 mmol) in hydrogen fluoride-pyridine (10 mL) at -10C. After stirring at room temperature for two hours, water (100 mL) and sodium bicarbonate were added to the reaction mixture at 0C, followed by extraction with ethyl acetate (100 mL). Then, the organic layer was washed with water (100 mL) twice and dried over anhydrous sodium sulfate. After concentration under reduced pressure, the residue was purified by silica gel chromatography (methylene chloride) to obtain the title compound (1.56 g, 42%) as a brown liquid. 1H-NMR (400 MHz, CDCl3): delta ppm: 7.78 (1H, dt, J = 2.7, 6.7 Hz), 8.02 (1H, dd, J = 1.6, 2.4 Hz). |
With pyridine hydrogenfluoride; sodium nitrite; at 10 - 20℃; for 2h; | To a mixture of <strong>[869557-43-7]3-bromo-5-fluoropyridin-2-amine</strong> (1.50 g, 7.85 mmol) and hydrogen fluoride pyridine (4 mL, 44 mmol), sodium nitrite (0.813 g, 11.8 mmol) was added at -10C in a several portions, and the mixture was stirred at room temperature for 2 hours. The mixture was diluted by addition of a saturated aqueous solution of sodium bicarbonate until it became basic, followed by extraction with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate. After filtration, the solvent was distilled off under reduced pressure to obtain a crude product of 3-bromo- 2, 5-difluoropyridine . | |
With pyridine hydrofluoride; sodium nitrite; at -10 - 20℃; for 2h; | To a mixture of 3-bromo-5-fluoro-pyridin-2-amine(1.50 g, 7.85 mmol) and hydrogen fluoride pyridine (4 mL, 44 mmol), sodium nitrite was added at -10C in a several portions, and the mixture was stirred at room temperature for 2 hours. The mixture was diluted by addition of asaturated aqueous solution of sodium bicarbonate until it became basic, followed by extraction with ethyl acetate.The organic layer was washed with a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate. After filtration, the solvent was distilled off under reduced pressure to obtain a crude product of 3-bromo-2,5-difluoro-pyridine (1.00 g) . To a solution of a crude product of 3-bromo-2,5-difluoro- pyridine (1.00 g) obtained in the above step in ethanol (20 mL), a 20% ethanol solution of sodium ethoxide (2.84 mL, 6.61 mmol) was added at room temperature, andthe mixture was stirred at 80C for 1 hour in an oil bath.The mixture was cooled, and concentrated under reducedpressure. The residue was purified in an automaticchromatography apparatus (n-hexane/ethyl acetate = 100/0- 90/10) to obtain the title compound (1.04 g, yield for2 steps: 66%)?H NNR spectrum (CDC13, 400MHz) oe: 8.02 (1H, d, J =2.3 Hz), 7.80 (1H, d, J= 2.3 Hz), 4.41 (2H, q, J=7.0 Hz), 1.43 (3H, t, J = 7.0 Hz) | |
With pyridine hydrofluoride; sodium nitrite; at -10 - 60℃; for 1.5h; | 3-Bromo-5-fluoro-pyridin-2-ylamine (2.17 g, 11.361 mmol) was taken in pyridine hydrogen fluoride (15 mL) and cooled at -10 C. Sodium nitrite (1.176 g, 17.042 mmol) was added portionwise over 30 minutes. The mixture was allowed to come to room temperature and finally heated at 60 C. for 1 h. The mixture was poured onto crushed ice (ca 50 g). The mixture was neutralized with 1M Na2CO3 and organics extracted with EA (2*100 mL). The organic layers were further washed with brine, dried over MgSO4, filtered and concentrated to the crude 3-bromo-2,5-difluoro-pyridine as a brownish oil (1.48 g, 66%). |