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CAS No. : | 401815-98-3 | MDL No. : | MFCD04112534 |
Formula : | C5H5BFNO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | WXGBZJJAGLSBPR-UHFFFAOYSA-N |
M.W : | 140.91 | Pubchem ID : | 2783396 |
Synonyms : |
|
Chemical Name : | (2-Fluoropyridin-4-yl)boronic acid |
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: |
* 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 |
---|---|---|
With potassium phosphate;dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate; In iso-butanol; at 100℃; for 10h;Inert atmosphere; | To a flask containing <strong>[197376-47-9]ethyl 2-(6-chloropyridin-3-yl)acetate</strong> 208-1 (300 mg, 1.5 mmol), 2-fluoropyridin-4-ylboronic acid 205-4 (318 mg, 2.25 mmol), Pd(OAc)2 (17 mg, 0.075 mmoL), 2-dicyclohexylphosphino-2',6'-dimethoxyybiphenyl (62 mg, 0.15 mmol), K3PO4 (800 mg, 9 mmol) under argon was added 2-butanol (1.5 rnL). The reaction mixture was stirred at 100 0C for 10 hours. After cooled to room temperature, the mixture was diluted with ethyl acetate, washed with water and brine, dried over Na2SO4, and concentrated to dryness by rotary evaporation. The crude was purified by silica gel flash chromatography, eluted with 40% ethyl acetate in dichloromethane to give ethyl 2-(2'-fluoro-2,4'-bipyridin-5-yl)acetate 208-2 as a yellow solid. MS m/z 261.1 (M + 1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; water; toluene; at 120℃; | To a sealed tube were added <strong>[121554-10-7]5-bromo-2-iodobenzonitrile</strong> 206-1 (500 mg, 1.6 mmol), 2-fluoropyridin-4-ylboronic acid 205-4 (229mg, 1.6 mmol), Pd(PPh3)4 (94 mg, 0.08 mmol), Na2CO3 ( 516 mg, 4.9 mmol), toluene (2 mL),H2O (2 mL) and ethanol (0.5 mL). The reaction mixture was stirred at 120 C overnight. After cooling to room temperature, the solvents were evaporated and the residue was redissolved in water (5 ml) and extracted with ethyl acetate (8 mL x 3). The combined organic phases were dried over Na2SO4, and concentrated. The residue was purified by silica gel flash chromatography and eluted with 15% ethyl acetate in hexane to give 5-bromo-2-(2-fluoropyridin-4-yl)benzonitrile 206-3. MS m/z 277 '.1 (M + 1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62.2% | With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate; In 1,2-dimethoxyethane; water; for 2.0h;Reflux; | A solution of 6g (771 mg, 2.012 mmol), (2-fluoro-4-pyridinyl)boronic acid (425 mg, 3.02 mmol),bis(triphenylphosphine)palladium(II) chloride (70.6 mg, 0.101 mmol) and Na2CO3 (1066 mg,10.06 mmol) in DME (20 mL) and water (2 mL) was stirred at reflux for 2 hours. The mixturewas then diluted with EA (50 mL) and water (50 mL). The organic layer was separated and theaqueous layer was extracted with ethyl acetate (50 mL*2). The combined organic layer wasconcentrated and the crude was purified by silica gel eluting with 0-10% MeOH/DCM (1%ammonia) to give the title compound 8i (500 mg, 1.252 mmol, 62.2 % yield) as an off-white solid. |
With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; for 2.0h;Reflux; | (2-Fluoro-4-pyridinyl)boronic acid (425 mg, 3.02 mmol),bis(triphenylphosphine)palladium(ll) chloride (70.6 mg, 0.10 mmol) and sodium carbonate (1066 mg, 10.06 mmol) as a solution in 2 ml of water was added to a solution of 5-bromo-2-[(phenylmethyl)oxy]-N-3-pyridinylbenzamide (may be prepared as described in example 2; 771 mg, 2.01 mmol) in 1 ,2-dimethoxyethane (20 ml). The mixture was heated to reflux for 2 hours. The mixture was diluted with ethyl acetate (50 ml) and water (50 ml). The organic layer was separated and the aqueous layer was extracted with ethyl acetate (2 x 50 ml). The organics were combined and evaporated. The residue was purified by chromatography on silica eluting with 0- 0% methanol/ dichloromethane 1 % ammonia to yield the title compound as an off-white solid. 500 mg. MS (electrospray): m/z [ +H]+ = 400H NMR (400 MHz, CHLOROFORM-tf) 5.36 (2 H, s), 7.18 - 7.32 (2 H, m), 7.32 - 7.44 (2 H, m), 7.49 - 7.66 (6 H, m) ,7.89 (1 H, dd, J=8.55, 2.19 Hz), 8.01 (1 H, d, J=7.45 Hz), 8.12 (1 H, d, J=1.53 Hz), 8.25 (2 H, t, J=5.04 Hz), 8.60 (1 H, d, J=2.19 Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With sodium carbonate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,2-dimethoxyethane; water; at 140℃; for 0.666667h;microwave irradiation; | To a solution of intermediate B (300 mg, 1.2 mmol) in 6 mL of DME and 2 mL of water, 2-(fluoro)pyridin-4-ylboronic acid (719 mg, 5.1 mmol), Pd(dppf)Ci2 (160 mg, 0.13 mmol), and 2M a2C03 (324 mg, 3.06 mL) were added. The mixture was microwave heated at 140 C for about 40 min. The mixture was concentrated under reduced pressure and extracted with EtOAc. The combined organic phase was 8576.98-304 dried with Na2S04 and concentrated under reduced pressure. The crude material was purified by silica gel flash column chromatography (PE: EA=75%) to give the title compound as a white solid (200 mg, 65% yield). |
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