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[ CAS No. 124432-63-9 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 124432-63-9
Chemical Structure| 124432-63-9
Chemical Structure| 124432-63-9
Structure of 124432-63-9 * Storage: {[proInfo.prStorage]}
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Product Details of [ 124432-63-9 ]

CAS No. :124432-63-9 MDL No. :MFCD09972202
Formula : C7H5BrF3NO Boiling Point : -
Linear Structure Formula :- InChI Key :YUDYUCKEWCVXTE-UHFFFAOYSA-N
M.W : 256.02 Pubchem ID :14837018
Synonyms :

Calculated chemistry of [ 124432-63-9 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.29
Num. rotatable bonds : 2
Num. H-bond acceptors : 5.0
Num. H-bond donors : 0.0
Molar Refractivity : 43.43
TPSA : 22.12 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.92 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.31
Log Po/w (XLOGP3) : 2.73
Log Po/w (WLOGP) : 4.02
Log Po/w (MLOGP) : 2.38
Log Po/w (SILICOS-IT) : 3.05
Consensus Log Po/w : 2.9

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.36
Solubility : 0.113 mg/ml ; 0.00044 mol/l
Class : Soluble
Log S (Ali) : -2.85
Solubility : 0.363 mg/ml ; 0.00142 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.9
Solubility : 0.0326 mg/ml ; 0.000127 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 2.02

Safety of [ 124432-63-9 ]

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:

Application In Synthesis of [ 124432-63-9 ]

* 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 [ 124432-63-9 ]

[ 124432-63-9 ] Synthesis Path-Downstream   1~21

  • 1
  • [ 124432-63-9 ]
  • [ 74-88-4 ]
  • 2-methoxy-3-methyl-5-(trifluoromethyl)pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With n-butyllithium; EXAMPLE 6 Preparation of 2-Methoxy-3-methyl-5-(trifluoromethyl)pyridine A solution of 5.12 g (0.020 mol) of <strong>[124432-63-9]3-bromo-2-methoxy-5-(trifluoromethyl)pyridine</strong> in 60 ml of ether was cooled to -70 C. and blanketed with nitrogen. A solution containing 0.021 mole of butyl lithium (8.4 ml of 2.5 M) was added slowly with stirring keeping the temperature below about -65 C. and the mixture allowed to react for another 30 min. Methyl iodide (0.62 ml, 0.01 mol) was added to the mixture and stirring continued at -70 C. for about 30 min. The mixture was allowed to warm to about 20 C. and was then poured onto a mixture of ice and saturated aqueous ammonium chloride. The organic layer that formed was recovered. The aqueous layer was extracted with ether and the extract added to the organic layer. The combined organic materials were dried over sodium sulfate and concentrated by evaporation under reduced pressure. The residue was distilled to obtain 2.1 g (54 percent of theory) of the title compound as a colorless oil boiling at 67-69 C. at 24 mm pressure. The proton nmr spectrum was consistent with the assigned structure.
  • 2
  • [ 124432-63-9 ]
  • [ 124432-66-2 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; n-butyllithium; In N-methyl-acetamide; hexane; EXAMPLE 8 Preparation of 2-Methoxy-5-(trifluoromethyl)-3-pyridinecarboxaldehyde A solution of 5.18 g (0.020 mol) of <strong>[124432-63-9]3-bromo-2-methoxy-5-(trifluoromethyl)pyridine</strong> in 50 ml of ether was cooled to -100 C. and blanketed with nitrogen. A solution containing 0.024 mole of butyl lithium in hexane (15.0 ml of 1.6 M) was added slowly with stirring keeping the temperature below about -95 C. and the mixture was allowed to react for another 15 min. Dimethylformamide (7.5 ml, 0.097 mol) was added to the mixture at below -95 C. and stirring continued for about 30 min. The mixture was allowed to warm to about 20 C. and was then poured onto a mixture of ice and 1N hydrochloric acid. The mixture that formed was extracted with ether and the extract was dried over sodium sulfate and concentrated by evaporation under reduced pressure. The residue was distilled in a Kugelrohr apparatus to obtain 3.6 g (86 percent of theory) of the title compound as an oil which solidified to a white crystalline solid. The proton nmr spectrum was consistent with the assigned structure.
  • 3
  • [ 71701-92-3 ]
  • [ 124432-63-9 ]
YieldReaction ConditionsOperation in experiment
With sodium methylate; In methanol; EXAMPLE 5 (Preparation of 3-Bromo-2-methoxy-5-(trifluoromethyl)pyridine A mixture of 7.6 g of <strong>[71701-92-3]2-chloro-3-bromo-5-(trifluoromethyl)pyridine</strong>, 6.2 ml of 25 percent sodium methoxide in methanol (0.027 mol), and 20 ml of anhydrous methanol was prepared and allowed to react at ambient temperature with stirring for 16 hours. The mixture was then poured onto ice and the resulting mixture extracted with ether. The ether extract was extracted with water, dried over sodium sulfate, and concentrated by evaporation under reduced pressure and the residue was purified by distillation under reduced pressure to obtain 4.1 g (65 percent of theory) of the title compound as a colorless oil boiling at 86-88 C. at 21 mm pressure and having a refractive index at 19 C. of 1.4816. The proton nmr spectrum was consistent with the assigned structure. Anal: Calc for C7 H5 BrF3 NO % C, 32.84; % H, 1.97: % N, 5.47. Found % C, 32.79; % H, 1.95: % N, 5.52.
  • 4
  • [ 52334-81-3 ]
  • [ 124432-63-9 ]
  • 5
  • 2-methoxy-5-(trifluoromethyl)pyridine [ No CAS ]
  • [ 124432-63-9 ]
YieldReaction ConditionsOperation in experiment
34.7% In acetonitrile; at 0 - 20℃;Inert atmosphere; [0190] To a stirred solution of 2-methoxy 5-(trifluoromethyl)pyridine (4 g, 22.58 mmol) was dissolved in acetonitrile(50 ml) was added NBS (6 g, 33.87 mmol) portion wiseat oo C. The reaction mixture was stirred for overnight at RT.The solvent was removed under vacuum, quenched withwater (100 mL) and extracted with ethyl acetate. The combinedorganic layer was washed with water, brine, dried oversodium sulfate, and concentrated at reduced pressure to yield3-bromo-2-methoxy-5-(trifluoromethyl)pyridine (12) as apale yellow liquid (2 g, 34.7%).
  • 6
  • [ 124432-63-9 ]
  • (2-methoxy-5-(trifluoromethyl)pyridin-3-yl)methanol [ No CAS ]
  • 7
  • [ 124432-63-9 ]
  • 3-(chloromethyl)-2-methoxy-5-(trifluoromethyl)pyridine [ No CAS ]
  • 8
  • [ 67-56-1 ]
  • [ 124432-63-9 ]
  • [ 201230-82-2 ]
  • methyl 2-methoxy-5-(trifluoromethyl)nicotinate [ No CAS ]
YieldReaction ConditionsOperation in experiment
45.4% With triethylamine; In toluene; at 80℃; for 12.0h;Inert atmosphere; [0192] To a stirred solution of<strong>[124432-63-9]3-bromo-2-methoxy-5-(trifluoromethyl)pyridine</strong> (23) (1.2 g, 4.68 mmol) dissolved inmixture of methanol (1 0 ml)/toluene (1 0 was added triethylamine(1 ml, 7.65 mmol), [1,1'-Bis(diphenylphosphino)ferrocene]palladium(II) dichloride (70 mg, 0.102 mmol). Thereaction mixture was carbonylated under CO [ 5 kg] at 80 C.for 12 h. Then the solvent was filtered through celite andsolvent was concentrated on vacuum, get crude. The crudecompound was purified by using silica gel chromatographyeluting 30% ethyl acetate in hexaen to afford methyl2-methoxy-5-(trifluoromethyl)nicotinate (13) as a liquid (0.5 g,45.4%).
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; triethylamine; at 100℃; for 16.38h;Inert atmosphere; Example 129D methyl 2-methoxy-5-(trifluoromethyl)nicotinate To <strong>[124432-63-9]3-bromo-2-methoxy-5-(trifluoromethyl)pyridine</strong> (50 g, 195 mmol) and Pd-dppf (Heraeus) (1.32 g, 1.804 mmol) in a 300 mL stainless steel reactor was added methanol (250 mL) and triethylamine (54.4 mL, 391 mmol). The reactor was degassed with nitrogen several times carbon monoxide was added and the reaction was heated to 100+-5 C., for about 16.38 hours. The pressure was at 60 psi+-4 psi for 2.7 hours and at 21+-7 psi for rest of the reaction time ˜14 hours. Additional Pd-dppf (Heraeus) (0.82 g, 1.121 mmol) catalyst was added. The reactor was repeatedly degassed with nitrogen several times, carbon monoxide was added and the reaction was heated to 100+-5 C. for 10 hours. The crude product was concentrated to remove methanol. Ethyl acetate (400 mL) was added, followed by the addition of 150 mL saturated aqueous NH4Cl, and the organic layer was isolated. The aqueous layer was extracted with ethyl acetate (200 mL). The organic layers were combined, washed with brine, dried over Na2SO4, filtered, and passed through a silica gel plug to remove dark Pt/C. The filtrate was concentrated to provide 40.62 g of the desired crude product, which was directly used in the next step. 1H NMR (400 MHz, DMSO-d6) δ ppm=3.84 (s, 3H) 3.96 (s, 3H) 8.40 (br s, 1H) 8.81 (br s, 1H); MS (ESI+) m/z 236.1 (M+H)+.
  • 9
  • [ 124432-63-9 ]
  • (2S,3S,4S,5S)-ethyl 4-amino-3-(tert-butyl)-1-(cyclohexanecarbonyl)-5-phenylpyrrolidine-2-carboxylate [ No CAS ]
  • (2S,3S,4S,5S)-ethyl 3-(tert-butyl)-1-(cyclohexanecarbonyl)-4-((2-methoxy-5-(trifluoromethyl)pyridin-3-yl)amino)-5-phenylpyrrolidine-2-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tris-(dibenzylideneacetone)dipalladium(0); (4-(N,N-dimethylamino)phenyl)-di-tert-butylphosphine; caesium carbonate; In 1,4-dioxane; at 40℃; for 16.0h; The mixture of (2S,3S,4S,5S)-ethyl 4-amino-3-(tert-butyl)-1-(cyclohexanecarbonyl)-5-phenylpyrrolidine-2-carboxylate (Example 114B, 100 mg, 0.250 mmol), <strong>[124432-63-9]3-bromo-2-methoxy-5-(trifluoromethyl)pyridine</strong> (70.3 mg, 0.275 mmol), 4-(di-tert-butylphosphino)-N,N-dimethylaniline (6.63 mg, 0.025 mmol), cesium carbonate (96 mg, 0.499 mmol) and 1,4-dioxane (2 mL) in a vial was purged with N2 for ˜30 minutes when Pd2 (dba)3 (tris(dibenzylideneacetone)dipalladium(0), 11.43 mg, 0.012 mmol) was added. The reaction mixture was purged with N2 again for 10 minutes, and then heated at 40 C. for 16 hours. The mixture was filtered, and washed with ethyl acetate. The combined organic layer was concentrated. The residue was purified by chromatography, eluting with ethyl acetate in heptanes 0-40% to provide (2S,3S,4S,5S)-ethyl 3-(tert-butyl)-1-(cyclohexanecarbonyl)-4-((2-methoxy-5-(trifluoromethyl)pyridin-3-yl)amino)-5-phenylpyrrolidine-2-carboxylate, which was dissolved in methanol (4 mL) and aqueous 4 M aqueous HCl (1 mL). The mixture was stirred at 40 C. overnight. The solvent was removed and the residue was adjusted with 1 N HCl aqueous to pH ˜5. Purification of the resulting mixture using reverse phase HPLC with trifluoroacetic acid method provided (2S,3S,4S,5S)-3-(tert-butyl)-1-(cyclohexanecarbonyl)-4-((2-methoxy-5-(trifluoromethyl)pyridin-3-yl)amino)-5-phenylpyrrolidine-2-carboxylic acid (46 mg, 0.084 mmol, 33.6% yield) as trifluoroacetic acid salt. 1H NMR (400 MHz, dimethyl sulfoxide-d6) δ ppm 7.54-7.44 (m, 3H), 7.09 (dd, J=8.1, 6.5 Hz, 2H), 7.03 (t, J=7.2 Hz, 1H), 6.97 (d, J=2.1 Hz, 1H), 5.35 (d, J=7.2 Hz, 1H), 4.85 (d, J=10.5 Hz, 1H), 4.54 (s, 1H), 4.45 (d, J=3.7 Hz, 1H), 3.74 (s, 3H), 2.26 (t, J=3.7 Hz, 1H), 2.17 (s, 1H), 1.64 (s, 2H), 1.45 (s, 2H), 1.29-1.07 (m, 4H), 1.04 (s, 9H), 1.02 (s, 2H); MS (ESI+) m/z 548.2 (M+H)+.
  • 10
  • [ 124432-63-9 ]
  • methyl 2-methoxy-5-(trifluoromethyl)nicotinate [ No CAS ]
YieldReaction ConditionsOperation in experiment
40.62 g With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; triethylamine; In methanol; at 100℃; under 1086.04 - 3102.97 Torr; for 33.18h;Inert atmosphere; methyl 2-methoxy-5-(trifluoromethyl)nicotinate To <strong>[124432-63-9]3-bromo-2-methoxy-5-(trifluoromethyl)pyridine</strong> (50 g, 195 mmol) and Pd-dppf ([1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II), Heraeus, 1.32 g, 1.804 mmol) in a 300 mL stainless steel reactor was added methanol (250 mL) and triethylamine (54.4 mL, 391 mmol). The reactor was degassed with nitrogen several times and carbon monoxide and was heated to 100+-5 C. for 16.38 hours and at 60 psi.+-4 psi for 2.7 hours and 21+-7 psi (˜14 hours). Additional Pd-dppf (Heraeus) (0.82 g, 1.121 mmol) catalyst was added. The crude product was concentrated to remove methanol. Ethyl acetate (400 mL) was added, followed by addition of 150 mL of saturated aqueous NH4Cl, and the organic layer was isolated. The aqueous layer was extracted with ethyl acetate (200 mL). The organic layers were combined, washed with brine, dried over Na2SO4, filtered, and passed through a silica gel plug to remove dark Pt/C. The filtrate was concentrated to provide 40.62 g of the desired crude product, which was used directly in the next step. 1H NMR (400 MHz, DMSO-d6) δ ppm=3.84 (s, 3H) 3.96 (s, 3H) 8.40 (br s, 1H) 8.81 (br s, 1H); MS (ESI+) m/z 236.1 (M+H)+.
  • 11
  • [ 124432-63-9 ]
  • (2S,3R,4S,5S)-3-tert-butyl-4-([2-methoxy-5-(trifluoromethyl)pyridin-3-yl](2H2)methyl}oxy)-5-(2-methylphenyl)-1-[(2S)-oxane-2-carbonyl]pyrrolidine-2-carboxylic acid [ No CAS ]
  • 12
  • [ 124432-63-9 ]
  • (2-methoxy-5-(trifluoromethyl)pyridin-3-yl)methanol-d2 [ No CAS ]
  • 13
  • [ 124432-63-9 ]
  • 3-(bromomethyl-d<SUB>2</SUB>)-2-methoxy-5-(trifluoromethyl)pyridine [ No CAS ]
  • 14
  • [ 124432-63-9 ]
  • (2S,3R,4S,5S)-2-ethyl 1-isopropyl 3-(tert-butyl)-5-phenyl-4-(prop-2-yn-1-yloxy)pyrrolidine-1,2-dicarboxylate [ No CAS ]
  • (2S,3R,4S,5S)-2-ethyl 1-isopropyl 3-(tert-butyl)-4-((3-(2-methoxy-5-(trifluoromethyl)pyridin-3-yl)prop-2-yn-1-yl)oxy)-5-phenylpyrrolidine-1,2-dicarboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); Example 277B (2S,3R,4S,5S)-2-ethyl 1-isopropyl 3-(tert-butyl)-4-((3-(2-methoxy-5-(trifluoromethyl)pyridin-3-yl)prop-2-yn-1-yl)oxy)-5-phenylpyrrolidine-1,2-dicarboxylate (2S,3R,4S,5S)-2-Ethyl 1-isopropyl 3-(tert-butyl)-4-((3-(2-methoxy-5-(trifluoromethyl)pyridin-3-yl)prop-2-yn-1-yl)oxy)-5-phenylpyrrolidine-1,2-dicarboxylate from Example 277A (58 mg, 0.098 mmol), <strong>[124432-63-9]3-bromo-2-methoxy-5-(trifluoromethyl)pyridine</strong> (30.5 mg, 0.119 mmol), copper(I) iodide (2.063 mg, 10.83 μmol) and tetrakis(triphenylphosphine)palladium(0) (12.51 mg, 10.83 μmol) were combined under nitrogen with nitrogen sparged toluene (289 μL) and triethylamine (144 μL). The resulting solution was heated to 60 C. for 3.5 hours. The solvent was removed under a stream of nitrogen. Diethyl ether was added, leaving behind a precipitate (PPh3O), which was filtered out. The filtrate was purified using a 10 g silica gel cartridge eluting with 0-20% ethyl acetate/heptanes over 20 minutes to give (2S,3R,4S,5S)-2-ethyl 1-isopropyl 3-(tert-butyl)-4-((3-(2-methoxy-5-(trifluoromethyl)pyridin-3-yl)prop-2-yn-1-yl)oxy)-5-phenylpyrrolidine-1,2-dicarboxylate. MS (APCI+) m/z 591 (M+H)+.
  • 15
  • [ 124432-63-9 ]
  • (2S,3R,4S,5S)-2-ethyl 1-isopropyl 3-(tert-butyl)-5-phenyl-4-(prop-2-yn-1-yloxy)pyrrolidine-1,2-dicarboxylate [ No CAS ]
  • (2S,3R,4S,5S)-3-(tert-butyl)-1-(isopropoxycarbonyl)-4-((3-(2-methoxy-5-(trifluoromethyl)pyridin-3-yl)prop-2-yn-1-yl)oxy)-5-phenylpyrrolidine-2-carboxylic acid [ No CAS ]
  • 16
  • [ 124432-63-9 ]
  • (2S,3R,4S,5S)-ethyl 3-(tert-butyl)-5-(2-ethylphenyl)-4-(prop-2-yn-1-yloxy)-1-((S)-tetrahydro-2H-pyran-2-carbonyl)pyrrolidine-2-carboxylate [ No CAS ]
  • (2S,3R,4S,5S)-ethyl 3-(tert-butyl)-5-(2-ethylphenyl)-4-((3-(2-methoxy-5-(trifluoromethyl)pyridin-3-yl)prop-2-yn-1-yl)oxy)-1-((S)-tetrahydro-2H-pyran-2-carbonyl)pyrrolidine-2-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); Example 278E (2S,3R,4S,5S)-ethyl 3-(tert-butyl)-5-(2-ethylphenyl)-4-((3-(2-methoxy-5-(trifluoromethyl)pyridin-3-yl)prop-2-yn-1-yl)oxy)-1-((S)-tetrahydro-2H-pyran-2-carbonyl)pyrrolidine-2-carboxylate (2S,3R,4S,5S)-Ethyl 3-(tert-butyl)-5-(2-ethylphenyl)-4-(prop-2-yn-1-yloxy)-1-((S)-tetrahydro-2H-pyran-2-carbonyl)pyrrolidine-2-carboxylate from Example 278D (100 mg, 0.213 mmol) and <strong>[124432-63-9]3-bromo-2-methoxy-5-(trifluoromethyl)pyridine</strong> (36.0 μL, 0.234 mmol), copper(I) iodide (4.06 mg, 0.021 mmol) and tetrakis(triphenylphosphine)palladium(0) (24.61 mg, 0.021 mmol) were combined under nitrogen with nitrogen sparged toluene (568 μL) and triethylamine (284 μL). The resulting solution was heated to 50 C. for 17 hours. The solvent was removed under a stream of nitrogen and the crude material was added to diethyl ether, leaving behind a precipitate (PPh3O). After filtration, the solid was rinsed with additional diethyl ether and the combined ether washes were purified using a 10 g silica gel cartridge eluting with 0-20% ethyl acetate/heptanes over 20 minutes to give (2S,3R,4S,5S)-ethyl 3-(tert-butyl)-5-(2-ethylphenyl)-4-((3-(2-methoxy-5-(trifluoromethyl)pyridin-3-yl)prop-2-yn-1-yl)oxy)-1-((S)-tetrahydro-2H-pyran-2-carbonyl)pyrrolidine-2-carboxylate. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.47 (dd, J=2.4, 1.2 Hz, 1H), 7.96 (dd, J=7.4, 1.3 Hz, 1H), 7.86 (d, J=2.5 Hz, 1H), 7.21-7.07 (m, 3H), 5.52 (s, 1H), 4.64 (d, J=1.9 Hz, 1H), 4.43 (d, J=5.8 Hz, 1H), 4.16 (qd, J=7.1, 1.8 Hz, 2H), 3.99 (s, 3H), 3.92 (d, J=16.7 Hz, 1H), 3.71 (d, J=16.7 Hz, 1H), 2.78-2.65 (m, 2H), 2.42 (d, J=1.9 Hz, 1H), 1.70-1.59 (m, 2H), 1.57-1.42 (m, 2H), 1.33 (tt, J=7.7, 4.2 Hz, 5H), 1.23 (td, J=7.3, 1.4 Hz, 6H), 1.03 (s, 9H); MS (APCI+) m/z 645 (M+H)+.
  • 17
  • [ 124432-63-9 ]
  • (2S,3R,4S,5S)-ethyl 3-(tert-butyl)-5-(2-ethylphenyl)-4-(prop-2-yn-1-yloxy)-1-((S)-tetrahydro-2H-pyran-2-carbonyl)pyrrolidine-2-carboxylate [ No CAS ]
  • (2S,3R,4S,5S)-3-(tert-butyl)-5-(2-ethylphenyl)-4-((3-(2-methoxy-5-(trifluoromethyl)pyridin-3-yl)prop-2-yn-1-yl)oxy)-1-((S)-tetrahydro-2H-pyran-2-carbonyl)pyrrolidine-2-carboxylic acid [ No CAS ]
  • 18
  • [ 124432-63-9 ]
  • (1-(methoxycarbonyl)cyclopropyl)zinc(II) bromide [ No CAS ]
  • methyl 1-(2-methoxy-5-(trifluoromethyl)-pyridin-3-yl)cyclopropanecarboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tris-(dibenzylideneacetone)dipalladium(0); monophosphine 1,2,3,4,5-pentaphenyl-1'-(di-tert-butylphosphino)ferrocene; In tetrahydrofuran; at 20℃; for 1.0h;Inert atmosphere; To <strong>[124432-63-9]3-bromo-2-methoxy-5-(trifluoromethyl)pyridine</strong> [CAS 124432-63-9] (2 g, 7.81 mmol) in 20 mL of dry 13 tetrahydrofuran was added Q-Phos (pentaphenyl(di-tert-butylphosphino)ferrocene, 0.122 g, 0.172 mmol) and Pd(dba)2 (tris(dibenzylideneacetone)dipalladium(0), 0.143 g, 0.156 mmol). A solution of freshly-prepared 10 (1-(methoxycarbonyl)cyclopropyl)zinc(II) bromide (2.86 g, 11.72 mmol) in tetrahydrofuran (0.5 mmol/mL, 30 mL) was added via a stainless steel cannula with 84 nitrogen pressure. The mixture was stirred at ambient temperature for one hour. 35 Dichloromethane (30 mL) and saturated 20 aqueous NH4Cl (10 mL) was added and the organic layer was washed with brine, dried over MgSO4, filtered, and concentrated. The residue was purified via chromatography on a 50 g silica gel cartridge, eluting with ethyl acetate/methanol (9:1) in 48 heptane at a 0-50% gradient to provide 85 methyl 1-(2-methoxy-5-(trifluoromethyl)-pyridin-3-yl)cyclopropanecarboxylate, HTP-LC/MS (APCI), m/z=276 (M+H)+. 85 Methyl 1-(2-methoxy-5-(trifluoromethyl)-pyridin-3-yl)cyclopropanecarboxylate was dissolved in 28 methanol (6 mL) and 87 lithium hydroxide (1.096 g, 45.8 mmol) in 25 water (1 mL). The mixture was stirred at 50 C. for 3 hours. The solvent was removed and the residue was adjusted pH to 12 by adding 2 N 88 aqueous HCl. The mixture was extracted using 35 dichloromethane and methanol (10:1). The extracts were washed with brine, dried over MgSO4, filtered, concentrated to dryness, and dried in an oven to provide the 89 title compound. HTP-LC/MS (APCI+) m/z 262.18 (M+H)+.
  • 19
  • [ 124432-63-9 ]
  • 1-[2-methoxy-5-(trifluoromethyl)pyridin-3-yl]-N-(naphthalene-1-sulfonyl)cyclopropane-1-carboxamide [ No CAS ]
  • 20
  • [ 124432-63-9 ]
  • 1-(2-methoxy-5-(trifluoromethyl)pyridin-3-yl)cyclopropanecarboxylic acid [ No CAS ]
  • 21
  • [ 124432-63-9 ]
  • (R)-2-(4-cyclopropylphenyl)-N-(pyrrolidin-3-yl)acetamide [ No CAS ]
  • (R)-2-(4-cyclopropylphenyl)-N-(1-(2-methoxy-5-(trifluoromethyl)pyridin-3-yl)pyrrolidin-3-yl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Example 128 (R)-2-(4-cyclopropylphenyl)-N-(1-(2-methoxy-5-(trifluoromethyl)pyridin-3-yl)pyrrolidin-3-yl)acetamide According to a technique similar to Example 9, the title compound (white crystals, 46 mg, 27%) was obtained using (R)-2-(4-cyclopropylphenyl)-N-(pyrrolidin-3-yl)acetamide (100 mg, 0.40 mmol) synthesized in Reference Example 74-2 and <strong>[124432-63-9]3-bromo-2-methoxy-5-(trifluoromethyl)pyridine</strong> (123 mg, 0.48 mmol). 1H NMR (CDCl3, 400 MHz): δ = 0.6 - 0.7 (m, 2H), 0.9 - 1.0 (m, 2H), 1.7 - 2.0 (m, 2H), 2.2 - 2.3 (m, 1H), 3.2 - 3.3 (m, 2H), 3.4 - 3.5 (m, 1H), 3.52 (s, 2H), 3.5 - 3.6 (m, 1H), 3.96 (s, 3H), 4.4 - 4.6 (m, 1H), 5.5 - 5.6 (m, 1H), 6.81 (d, 1H, J = 2 Hz), 7.03 (d, 2H, J = 8 Hz), 7.11 (d, 2H, J = 8 Hz), 7.86 (d, 1H, J = 2 Hz). MS: 420.16 [M+H]+
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Related Functional Groups of
[ 124432-63-9 ]

Fluorinated Building Blocks

Chemical Structure| 216766-05-1

[ 216766-05-1 ]

3-Bromo-2-ethoxy-5-(trifluoromethyl)pyridine

Similarity: 0.95

Chemical Structure| 216766-04-0

[ 216766-04-0 ]

3-Bromo-2-isopropoxy-5-(trifluoromethyl)pyridine

Similarity: 0.91

Chemical Structure| 76041-73-1

[ 76041-73-1 ]

3-Bromo-5-(trifluoromethyl)pyridin-2-ol

Similarity: 0.90

Chemical Structure| 1214377-42-0

[ 1214377-42-0 ]

5-Bromo-2-methoxy-3-(trifluoromethyl)pyridine

Similarity: 0.89

Bromides

Chemical Structure| 216766-05-1

[ 216766-05-1 ]

3-Bromo-2-ethoxy-5-(trifluoromethyl)pyridine

Similarity: 0.95

Chemical Structure| 216766-04-0

[ 216766-04-0 ]

3-Bromo-2-isopropoxy-5-(trifluoromethyl)pyridine

Similarity: 0.91

Chemical Structure| 76041-73-1

[ 76041-73-1 ]

3-Bromo-5-(trifluoromethyl)pyridin-2-ol

Similarity: 0.90

Chemical Structure| 1214377-42-0

[ 1214377-42-0 ]

5-Bromo-2-methoxy-3-(trifluoromethyl)pyridine

Similarity: 0.89

Ethers

Chemical Structure| 216766-05-1

[ 216766-05-1 ]

3-Bromo-2-ethoxy-5-(trifluoromethyl)pyridine

Similarity: 0.95

Chemical Structure| 216766-04-0

[ 216766-04-0 ]

3-Bromo-2-isopropoxy-5-(trifluoromethyl)pyridine

Similarity: 0.91

Chemical Structure| 1214377-42-0

[ 1214377-42-0 ]

5-Bromo-2-methoxy-3-(trifluoromethyl)pyridine

Similarity: 0.89

Trifluoromethyls

Chemical Structure| 216766-05-1

[ 216766-05-1 ]

3-Bromo-2-ethoxy-5-(trifluoromethyl)pyridine

Similarity: 0.95

Chemical Structure| 216766-04-0

[ 216766-04-0 ]

3-Bromo-2-isopropoxy-5-(trifluoromethyl)pyridine

Similarity: 0.91

Chemical Structure| 76041-73-1

[ 76041-73-1 ]

3-Bromo-5-(trifluoromethyl)pyridin-2-ol

Similarity: 0.90

Chemical Structure| 1214377-42-0

[ 1214377-42-0 ]

5-Bromo-2-methoxy-3-(trifluoromethyl)pyridine

Similarity: 0.89

Related Parent Nucleus of
[ 124432-63-9 ]

Pyridines

Chemical Structure| 216766-05-1

[ 216766-05-1 ]

3-Bromo-2-ethoxy-5-(trifluoromethyl)pyridine

Similarity: 0.95

Chemical Structure| 216766-04-0

[ 216766-04-0 ]

3-Bromo-2-isopropoxy-5-(trifluoromethyl)pyridine

Similarity: 0.91

Chemical Structure| 76041-73-1

[ 76041-73-1 ]

3-Bromo-5-(trifluoromethyl)pyridin-2-ol

Similarity: 0.90

Chemical Structure| 1214377-42-0

[ 1214377-42-0 ]

5-Bromo-2-methoxy-3-(trifluoromethyl)pyridine

Similarity: 0.89

Chemical Structure| 1254123-51-7

[ 1254123-51-7 ]

5-Bromo-3-(difluoromethyl)-2-methoxypyridine

Similarity: 0.86