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[ CAS No. 913373-43-0 ]

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Chemical Structure| 913373-43-0
Chemical Structure| 913373-43-0
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Product Details of [ 913373-43-0 ]

CAS No. :913373-43-0 MDL No. :MFCD03094988
Formula : C5H4BClFNO2 Boiling Point : 332.6°C at 760 mmHg
Linear Structure Formula :- InChI Key :-
M.W :175.35 g/mol Pubchem ID :-
Synonyms :

Safety of [ 913373-43-0 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 913373-43-0 ]

  • Downstream synthetic route of [ 913373-43-0 ]

[ 913373-43-0 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 913373-43-0 ]
  • [ 52522-99-3 ]
  • [ 952402-70-9 ]
YieldReaction ConditionsOperation in experiment
27% With sodium carbonate;palladium diacetate; triphenylphosphine; In propan-1-ol; for 4h;Heating / reflux; Preparation 70: 5-(2-Chloro-5-fluoro-pyridin-3-yl)-2,4-dimethoxy-pyrimidine (Prep70); <n="100"/>5-lodo-2,4-dimethoxy-pyrimidine (868 mg, 3.3 mmol) was dissolved in degassed n-PrOH (30 ml) and then 2-chloro-5-fluoropyridine-3-boronic acid (858 mg, 4.9 mmol), Na2CO3 (700 mg, 6.6 mmol), PPh3 (88 mg, 0.33 mmol) and Pd(OAc)2 (90 mg) were added. The suspension was stirred at reflux for 4 hours. The solvent was evaporated under vacuum and the crude was partitioned between brine and ethyl acetate. The organic phase was dried (Na2SO4) and evaporated. The crude was purified by flash chromatography with ethyl acetate-petroleum ether 2-8 affording 240 mg of the title compound (27% yield). MS (ES) (m/z): 270 [M+H]+.
  • 2
  • [ 913373-43-0 ]
  • [ 943152-85-0 ]
  • [ 943153-01-3 ]
YieldReaction ConditionsOperation in experiment
44% With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; at 150℃; for 0.166667h;Irradiation; (R)-N-{1-[4-(2-Chloro-5-fluoro-pyridin-3-yl)-phenyl]-ethyl}-3,4-difluoro-benzenesulfonamide To a solution of (R)-2-[1-(4-bromo-phenyl)-ethyl]-isoindole-1,3-dione (1.19 g, 3.6 mmol) (Example 26) in 1,2-dimethoxyethane (3 ml) was added <strong>[913373-43-0]2-chloro-5-fluoropyridine-3-boronic acid</strong> (0.95 g, 5.4 mmol), tetrakis(triphenylphosphine)palladium (0) (0.21 g, 0.2 mmol) and 2M aqueous sodium carbonate (3.2 ml, 6.4 mmol). The reaction mixture was heated in a microwave oven at 150 C. for 10 min and the solvent evaporated. The residue was partitioned between ethyl acetate and water. The organic phase washed with brine, dried over anhydrous magnesium sulfate and the solvent evaporated. The residue was purified over silica gel eluting with heptane/ethyl acetate to give (R)-2-{1-[4-(2-chloro-5-fluoro-pyridin-3-yl)-phenyl]-ethyl}-isoindole-1,3-dione (0.62 g, 1.6 mmol, 44%) as a clear glass. To a solution of (R)-2-[1-(4-bromo-phenyl)-ethyl]-isoindole-1,3-dione (0.16 g, 0:4 mmol) in methanol (4 ml) was added hydrazine hydrate (0.43 g, 8.6 mmol). The reaction mixture was stirred at room temperature for 18 h and then concentrated under reduced pressure. Dichloromethane was added and the resultant white precipitate filtered off. The solvent was evaporated to give 1-[4-(2-chloro-5-fluoro-pyridin-3-yl)-phenyl]-ethylamine (0.11 g, 0.4 mmol, 100%) as a yellow gum. To a solution of (R)-1-[4-(2-chloro-5-fluoro-pyridin-3-yl)-phenyl]-ethylamine (26 mg, 0.1 mmol) in dichloromethane (1 ml) was added triethylamine (31.6 mg, 0.31 mmol) followed by 3,4-difluorobenzenesulfonyl chloride (28.7 mg, 0.14 mmol). The reaction mixture was agitated for 64 h at room temperature and the solvent evaporated. The crude product was taken up in dimethyl sulfoxide (1 ml) and purified by preparatory LCMS. The solvent was evaporated under reduced pressure to give the title compound (6.7 mg, 0.04 mmol, 38%). 1H NMR (400 MHz, DMSO-d6): δ 8.48 (m, 2H), 7.78 (dd, 1H), 7.45-7.60 (m, 3H), 7.27-7.34 (m, 4H), 4.50 (q, 1H), 1.33 (d, 3H) ppm; MS (ESI) m/z: 427 [M+H]+.
  • 3
  • [ 913373-43-0 ]
  • [ 1065481-12-0 ]
  • [ 1065481-45-9 ]
YieldReaction ConditionsOperation in experiment
With cesium fluoride;copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; at 100℃; for 1h;Microwave irradiation; Example 80; <n="132"/>A mixture of (S)-2-(l-(2,8-dichloroquinolin-3-yl)ethyl)isoindoline-l,3-dione (120.0 mg, 323 μmol), <strong>[913373-43-0]2-chloro-5-fluoropyridin-3-ylboronic acid</strong> (57 mg, 323 μmol), tetrakis(triphenylphosphine)palladium (37 mg, 32 μmol), cesium fluoride (147 mg, 970 μmol) and copper(I) iodide (12 mg, 65 μmol) in 1 ,2-ethanediol, dimethyl ether (3.0 mL, 323 μmol) was subjected to microwave at 100 0C for 1 h, cooled to room temperature. Filtration of the resultant mixture and rinsed with EtOAc, the filtrates were collected and concentrated. Purification of the residue by flash chromatography over silica gel, gradient elution, 0-100% EtOAc in hexane, gave 2-((S)- 1 -(8-chloro-2-(2-chloro-5-fluoropyridin-3-yl)quinolin-3-yl)- ethyl)isoindoline-l,3-dione, Mass Spectrum (ESI) m/e = 466.0 (M + 1).
  • 4
  • [ 5419-55-6 ]
  • [ 884494-36-4 ]
  • [ 913373-43-0 ]
YieldReaction ConditionsOperation in experiment
To a solution of n-BuLi/THF (1.45 mL, 2.5 mol/L) in THF (5 mL) was added asolution of <strong>[884494-36-4]3-bromo-2-chloro-5-fluoropyridine</strong> (630 mg, 3.0 mmol) in THF (5 mL) dropwise at-78 C. The reaction mixture was stirred at -78 C for another 30 minutes, followed by the addition of B(OiPr)3 (677 mg, 3.6 mmol) in THF (2 mL). The mixture was stirred at -78C for another 2 h, and quenched with 5% NaOH aqueous solution (10 mL). The mixture was acidified to pH 12 with dilute aqueous HC1 solution, and extracted with EA (60 mL x 3). Thecombined organic phases were dried over anhydrous MgSO4 and filtered. The filtrate was concentrated in vacuo to afford 2-chloro-5-fluoropyridin-3-ylboronic acid (1.5 g, crude) as grey oil, which was used in the next step without further purifications. LC-MS m/z: 176.1 [M+Hjt tR= 0.64 min.
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