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[ CAS No. 114153-09-2 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
Chemical Structure| 114153-09-2
Chemical Structure| 114153-09-2
Structure of 114153-09-2 * Storage: {[proInfo.prStorage]}
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Product Details of [ 114153-09-2 ]

CAS No. :114153-09-2 MDL No. :MFCD11519029
Formula : C7H7F2N Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 143.13 Pubchem ID :-
Synonyms :

Safety of [ 114153-09-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 114153-09-2 ]

* 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 [ 114153-09-2 ]

[ 114153-09-2 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 64695-79-0 ]
  • [ 114153-09-2 ]
  • 2
  • [ 1211589-41-1 ]
  • [ 114153-09-2 ]
  • [ 2785392-63-2 ]
YieldReaction ConditionsOperation in experiment
72.9% Stage #1: methyl 5-bromo-2-(trifluoromethyl)isonicotinate; 3,4-difluoro-2-methylaniline With tris-(dibenzylideneacetone)dipalladium(0); Cs2CO3; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In 1,4-dioxane at 100℃; Inert atmosphere; Stage #2: With sodium hydroxide In 1,4-dioxane at 65℃; for 29220h; Inert atmosphere; Stage #3: With hydrogenchloride In lithium hydroxide monohydrate Cooling; 5-((3,4-Difluoro-2-methylphenyl)amino)-2-(trifluoromethyl)isonicotinic acid, hydrochloride To a mixture of methyl 5-bromo-2-(trifluoromethyl)isonicotinate (14 g, 49.3 mmol) and 3,4-difluoro-2-methylaniline (8.47 g, 59.1 mmol) in 1,4-dioxane (224 mL) was added cesium carbonate (32.1 g, 99 mmol), then Pd2(dba)3 (2.257 g, 2.465 mmol) and 2,2'- bis(diphenylphosphaneyl)-1,1'-binaphthalene (3.07 g, 4.93 mmol). The mixture was stirred at 100 °C under nitrogen overnight. The reaction was cooled and then filtered through celite. The crude solution was heated at 65°C with 5N sodium hydroxide (49.3 mL, 246 mmol) for 40m. The solution was cooled, and 75mL of 6N HCl was added and allowed to stir to give a yellow suspension. This was filtered to give solid, a second crop was also collected and the solids combined and slurried with 100mL diethyl ether, sonicated and filtered to give a lemon yellow solid, which was dried for 18h under vacuum to provide 5-((3,4-difluoro-2- methylphenyl)amino)-2-(trifluoromethyl)isonicotinic acid, hydrochloride as a yellow solid (13.25g, 35.9 mmol, 72.9% yield). MS (m/z) 331.1 (M+H)+.1H NMR (400 MHz, DMSO-d6) δ 9.47 (s, 1 H) 8.06 - 8.16 (m, 1 H) 7.97 - 8.06 (m, 1 H) 7.30 - 7.41 (m, 1 H) 7.18 - 7.31 (m, 1 H) 3.37 (br s, 3 H) 2.17 (s, 3 H).
72.9% Stage #1: methyl 5-bromo-2-(trifluoromethyl)isonicotinate; 3,4-difluoro-2-methylaniline With tris-(dibenzylideneacetone)dipalladium(0); Cs2CO3; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In 1,4-dioxane at 100℃; Inert atmosphere; Stage #2: With sodium hydroxide In 1,4-dioxane at 65℃; for 29220h; Inert atmosphere; Stage #3: With hydrogenchloride In lithium hydroxide monohydrate Cooling; 5-((3,4-Difluoro-2-methylphenyl)amino)-2-(trifluoromethyl)isonicotinic acid, hydrochloride To a mixture of methyl 5-bromo-2-(trifluoromethyl)isonicotinate (14 g, 49.3 mmol) and 3,4-difluoro-2-methylaniline (8.47 g, 59.1 mmol) in 1,4-dioxane (224 mL) was added cesium carbonate (32.1 g, 99 mmol), then Pd2(dba)3 (2.257 g, 2.465 mmol) and 2,2'- bis(diphenylphosphaneyl)-1,1'-binaphthalene (3.07 g, 4.93 mmol). The mixture was stirred at 100 °C under nitrogen overnight. The reaction was cooled and then filtered through celite. The crude solution was heated at 65°C with 5N sodium hydroxide (49.3 mL, 246 mmol) for 40m. The solution was cooled, and 75mL of 6N HCl was added and allowed to stir to give a yellow suspension. This was filtered to give solid, a second crop was also collected and the solids combined and slurried with 100mL diethyl ether, sonicated and filtered to give a lemon yellow solid, which was dried for 18h under vacuum to provide 5-((3,4-difluoro-2- methylphenyl)amino)-2-(trifluoromethyl)isonicotinic acid, hydrochloride as a yellow solid (13.25g, 35.9 mmol, 72.9% yield). MS (m/z) 331.1 (M+H)+.1H NMR (400 MHz, DMSO-d6) δ 9.47 (s, 1 H) 8.06 - 8.16 (m, 1 H) 7.97 - 8.06 (m, 1 H) 7.30 - 7.41 (m, 1 H) 7.18 - 7.31 (m, 1 H) 3.37 (br s, 3 H) 2.17 (s, 3 H).
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