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Chemical Structure| 1159811-44-5 Chemical Structure| 1159811-44-5

Structure of 1159811-44-5

Chemical Structure| 1159811-44-5

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Product Details of [ 1159811-44-5 ]

CAS No. :1159811-44-5
Formula : C5H4BrClFN
M.W : 212.45
SMILES Code : Cl.BrC1=C(C=NC=C1)F
MDL No. :MFCD03092937
InChI Key :NNSNDHTUFCXSAS-UHFFFAOYSA-N
Pubchem ID :44181861

Safety of [ 1159811-44-5 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H332-H335
Precautionary Statements:P261-P280-P305+P351+P338

Application In Synthesis of [ 1159811-44-5 ]

* 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 [ 1159811-44-5 ]

[ 1159811-44-5 ] Synthesis Path-Downstream   1~7

  • 1
  • [ 1159811-44-5 ]
  • [ 1401098-23-4 ]
  • [ 1401098-16-5 ]
YieldReaction ConditionsOperation in experiment
38.8% With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In tetrahydrofuran; at 100.0℃; for 3.0h;Microwave irradiation; Step A: Preparation of tert-Butyl 4-((4-(3-Fluoropyridin-4-yl)cyclohex-3- enyloxy)methyl)piperidine-l-carboxylate (Compound 57).; A mixture of <strong>[1159811-44-5]4-bromo-3-fluoropyridine hydrochloride</strong> (79 mg, 0.372 mmol), tert-butyl 4-((4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)cyclohex-3-enyloxy)methyl)piperidine-l- carboxylate (93.3 mg, 0.155 mmol), 2 M Na2C03 (400 μ, 0.800 mmol), and tetrakis (0.010 g, 8.7 μιηο) in 4 ml THF was heated under microwave irradiation at 100C for 3 h. Mixture was purified by HPLC (H20/CH3CN gradient + 0.1% TFA). Fractions containing desired product were partly concentrated and residue was extracted with 1 M NaOH and CH2C12. Organic phases were dried over MgS04, filtered, and concentrated to give tert-butyl 4-((4-(3- fluoropyridin-4-yl)cyclohex-3-enyloxy)methyl)piperidine-l-carboxylate (23.5 mg, 60.18 μηιο, 38.8 %) as an oil. Exact mass calculated for C23H31F3N203: 440.24, found: LCMS m/z = 441.6 (M+H+); lU NMR (400 MHz, CDC13) δ ppm 1.09-1.20 (m, 2H), 1.46 (s, 9H), 1.69-1.84 (m, 4H), 1.97-2.04 (m, 1H), 2.19-2.28 (m, 1H), 2.38-2.60 (m, 3H), 2.66-2.74 (m, 2H), 3.31-3.40 (m, 2H), 3.59-3.65 (m, 1H), 4.06-4.15 (m, 2H), 6.09-6.12 (m, 1H), 7.15-7.18 (m, 1H), 8.31-8.33 (m, 1H), 8.38 (d, 7 = 3.1 Hz. 1H).
  • 2
  • [ 1159811-44-5 ]
  • (-)-R-tert-butyl 4-(aminomethyl)-3,3-difluoropiperidine-1-carboxylate [ No CAS ]
  • (R)-tert-butyl 3,3-difluoro-4-(((3-fluoropyridin-4-yl)amino)methyl)piperidine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
55% With dicyclohexyl[3,6-dimethoxy-2′,4′,6′-tris(1-methylethyl)[1,1′-biphenyl]-2-yl]phosphine; chloro[2-(dicyclohexylphosphino)-3,6-dimethoxy-2′,4′,6′-tri-1-propyl-1,1′-biphenyl][2-(2-aminoethyl)phenyl]palladium(II); caesium carbonate; In 1,4-dioxane; at 110.0℃;Inert atmosphere; To a stirred solution of (R)-tert-butyl 4-(aminomethyl)-3,3-difluoropiperidine-l- carboxylate (1.02 g, 4.1 mmol) and <strong>[1159811-44-5]4-bromo-3-fluoropyridine hydrochloride</strong> (1.05 g, 4.9 mmol) in dioxane (15 mL) was added Pd-Gl (67 mg, 0.08 mmol), Brettphos (67 mg, 0.12 mmol) and CS2CO3(3.4 g, 10.3 mmol) under nitrogen atmosphere. The resulting mixture was heated to 110 C and stirred at 110 C overnight. The mixture allowed to cool to room temperature and was diluted with ethyl acetate and filtered through celite. The filtrate was concentrated under reduced pressure. The residue was purified by column chromatography over silica gel (eluent: hexane/ethyl acetate = 2: 1) to afford the title product as a light brown solid (1.53 g, 55%). MS (ESI) calculated for Ci6H22F3N302: 345.2 m/z; found: 346.2 m/z [M+H]. 1H MR (400 MHz, CDCI3) δ 8.14 (d, J= 3.2 Hz, 1H), 8.10 (d, J= 5.6 Hz, 1H), 6.58 (dd, J= 5.6, 7.6 Hz, 1H), 4.66- 4.58 (m, 1H), 4.53-4.05 (m, 2H), 3.71-3.63 (m, 1H), 3.28-3.19 (m, 1H), 3.07-2.65 (m, 2H), 2.24- 2.03 (m, 1H), 1.91-1.82 (m, 1H), 1.66-1.53 (m, 1H), 1.47 (s, 9H).
  • 3
  • [ 1159811-44-5 ]
  • 4-ethynyl-3-fluoropyridine [ No CAS ]
  • 4
  • [ 1159811-44-5 ]
  • ethyl 5-(3-fluoropyridin-4-yl)isoxazole-3-carboxylate [ No CAS ]
  • 5
  • [ 1159811-44-5 ]
  • 5-(3-fluoropyridin-4-yl)isoxazole-3-carboxylic acid [ No CAS ]
  • 6
  • [ 1159811-44-5 ]
  • N-(1-benzyl-1H-pyrazol-4-yl)-5-(3-fluoropyridin-4-yl)isoxazole-3-carboxamide [ No CAS ]
  • 7
  • [ 1159811-44-5 ]
  • [ 1066-54-2 ]
  • 3-fluoro-4-((trimethylsilyl)ethynyl)pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
73% With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; at 60.0℃; for 18.0h;Inert atmosphere; Step 1: Preparation of 3-fluoro-4-((trimethylsilyl)ethynyl)pyridine A mixture of <strong>[1159811-44-5]4-bromo-3-fluoropyridine hydrochloride</strong> (3 g, 14.2 mmol), bis(triphenylphosphine)palladium(II) chloride (0.5 g, 0.7 mmol), copper iodide (0.27 g, 1.41 mmol) in triethylamine (20 mL) was degassed and re-filled with nitrogen three times. Then ethynyltrimethylsilane (6 mL, 42.5 mmol) was added dropwise by a syringe. After the addition, the reaction was stirred at 60 C. for 18 h. The reaction mixture was diluted with water (100 mL) and extracted with ethyl acetate (100 mL*2). The combined organic phases were washed with brine (80 mL), dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography (Biotage, 40 g silica, eluted with ethyl acetate in petroleum ether from 10% to 15%) to give 3-fluoro-4-((trimethylsilyl)ethynyl)pyridine (2 g, 10.4 mmol, 73%) as a yellow oil. LCMS (ESI) m/z: 194.1 [M+H]+.
 

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