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Chemical Structure| 82671-06-5 Chemical Structure| 82671-06-5
Chemical Structure| 82671-06-5

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CAS No.: 82671-06-5

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Product Details of 2,6-Dichloro-5-fluoronicotinic acid

CAS No. :82671-06-5
Formula : C6H2Cl2FNO2
M.W : 209.99
SMILES Code : O=C(C1=CC(F)=C(Cl)N=C1Cl)O
MDL No. :MFCD00799517
InChI Key :LTDGKGCHRNNCAC-UHFFFAOYSA-N
Pubchem ID :2733659

Safety of 2,6-Dichloro-5-fluoronicotinic acid

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of 2,6-Dichloro-5-fluoronicotinic acid

* 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 [ 82671-06-5 ]

[ 82671-06-5 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 33024-60-1 ]
  • [ 82671-06-5 ]
  • [ 1352624-89-5 ]
YieldReaction ConditionsOperation in experiment
39% With N-ethyl-N,N-diisopropylamine; In acetonitrile; at 130℃; for 21h;Microwave irradiation; PREPARATION 79 5-Chloro-6-fluoro-3-(tetrahydro-2H-pyran-4-yl)-1-[2-(trimethylsilyl)ethoxy] methyl}-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one [Show Image]a) 6-Chloro-5-fluoro-2-(tetrahydro-2H-pyran-4-ylamino)nicotinic acid A mixture of 2,6-dichloro-5-fluoronicotinic acid (1.01 g, 4.8 mmol), diisopropylethylamine (11 mL, 62.5 mmol) and <strong>[33024-60-1]tetrahydro-2H-pyran-4-amine hydrochloride</strong> (3.30 g, 24 mmol) in acetonitrile (5 mL) was stirred and heated under microwave irradiation ("Initiator sixty" from Biotage.(R).) at 130 °C for 21 hours. The mixture was then cooled and dichloromethane was added and the organic layer was washed with 5percent aqueous citric acid, water, brine, dried (MgSO4) and the solvent was evaporated. The residue was purified by reverse phase chromatography (C-18 silica from Waters.(C)., water/acetonitrile/methanol as eluents [0.1percent v/v formic acid buffered] 0percent to 100percent) to give the title compound (0.51 g, 39percent) of as a white solid. LRMS (m/z): 273 (M-1)+.1H NMR (300 MHz, CDCl3) delta ppm 1.48 - 1.69 (m, 2H), 1.97 - 2.14 (m, 2H), 3.58 (t, 2H), 4.03 (dd, 2H), 4.29 (ddd, 1H), 5.04 (d, 1H), 7.84 (d, 1H).
39% With N-ethyl-N,N-diisopropylamine; In acetonitrile; at 130℃; for 21h;Microwave irradiation; PREPARATION 79 5-Chloro-6-fluoro-3-(tetrahydro-2H-pyran-4-yl)-1-[2-(trimethylsilyl)ethoxy] methyl}-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one a) 6-Chloro-5-fluoro-2-(tetrahydro-2H-pyran-4-ylamino)nicotinic acid A mixture of 2,6-dichloro-5-fluoronicotinic acid (1.01 g, 4.8 mmol), diisopropylethylamine (11 mL, 62.5 mmol) and <strong>[33024-60-1]tetrahydro-2H-pyran-4-amine hydrochloride</strong> (3.30 g, 24 mmol) in acetonitrile (5 mL) was stirred and heated under microwave irradiation ("Initiator sixty" from Biotage.(R).) at 130 °C for 21 hours. The mixture was then cooled and dichloromethane was added and the organic layer was washed with 5percent aqueous citric acid, water, brine, dried (MgSO4) and the solvent was evaporated. The residue was purified by reverse phase chromatography (C-18 silica from Waters.(C)., water/acetonitrile/methanol as eluents [0.1percent v/v formic acid buffered] 0percent to 100percent) to give the title compound (0.51 g, 39percent) of as a white solid. LRMS (m/z): 273 (M-1)+.1H NMR (300 MHz, CDCl3) delta ppm 1.48 - 1.69 (m, 2H), 1.97 - 2.14 (m, 2H), 3.58 (t, 2H), 4.03 (dd, 2H), 4.29 (ddd, 1H), 5.04 (d, 1H), 7.84 (d, 1H).
39% a)6-Chloro-5-fluoro-2-(tetrahydro-2H-pyran-4-ylamino)nicotinic acidA mixture of 2,6-dichloro-5-fluoronicotinic acid (1.01 g, 4.8 mmol), diisopropylethylamine (11 mL, 62.5 mmol) and <strong>[33024-60-1]tetrahydro-2H-pyran-4-amine hydrochloride</strong> (prepared as described in ), 3.30 g, 24 mmol) in acetonitrile (5 mL) was stirred and heated under microwave irradiation at 130 °C for 21 hours.The mixture was then cooled, dichloromethane was added and the organic layer was washed with 5percent aqueous citric acid solution, water and brine, dried (MgSO4) and the solvent was evaporated.The residue was purified by reverse phase chromatography (C-18 silica from Waters?, water/acetonitrile/methanol as eluents [0.1percent v/v formic acid buffered] 0percent to 100percent) to give the title compound (0.51 g, 39percent) as a white solid.LRMS (m/z): 273 (M-1)+.1H NMR delta (300 MHz, CDCl3): 1.48-1.69 (m, 2H), 1.97-2.14 (m, 2H), 3.58 (t, 2H), 4.03 (dd, 2H), 4.29 (ddd, 1H), 5.04 (d, 1H), 7.84 (d, 1H).
39% With N-ethyl-N,N-diisopropylamine; In acetonitrile; at 130℃; for 21h;microwave irradiation; a) 6-Chloro-5-fluoro-2-(tetrahydro-2H-pyran-4-ylamino)nicotinic acidA mixture of 2,6-dichloro-5-fluoronicotinic acid (1 .01 g, 4.8 mmol), diisopropylethylamine (1 1 ml_, 62.5 mmol) and tetrahydro-2/-/-pyran-4-amine hydrochloride (prepared as described in WO200424728(A2), 3.30 g, 24 mmol) in acetonitrile (5 mL) was stirred and heated under microwave irradiation at 130 °C for 21 hours. The mixture was then cooled, dichloromethane was added and the organic layer was washed with 5percent aqueous citric acid solution, water and brine, dried (MgS04) and the solvent was evaporated. The residue was purified by reverse phase chromatography (C-18 silica from Waters.(C)., water/acetonitrile/methanol as eluents [0.1 percent v/v formic acid buffered] 0percent to 100percent) to give the title compound (0.51 g, 39percent) as a white solid.LRMS (m/z): 273 (M-1 )+.1H NMR delta (300 MHz, CDCI3): 1 .48-1 .69 (m, 2H), 1 .97-2.14 (m, 2H), 3.58 (t, 2H), 4.03 (dd, 2H), 4.29 (ddd, 1 H), 5.04 (d, 1 H), 7.84 (d, 1 H).

  • 2
  • [ 33024-60-1 ]
  • [ 82671-06-5 ]
  • [ 1352624-90-8 ]
  • 3
  • [ 82671-06-5 ]
  • [ 932705-78-7 ]
  • 4
  • [ 82671-06-5 ]
  • [ 959616-64-9 ]
  • 5
  • [ 82671-06-5 ]
  • [ 886372-63-0 ]
 

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