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Chemistry
Organometallic Reagents
Organoboron
Organoboron ∩ Alkenyls
2-((Difluoromethyl)sulfonyl)pyridine
Chemistry
Organometallic Reagents
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Pyridines Fluorinated Building Blocks Sulfones Difluoromethyls Alkenes Fluorination Reagents
Organoboron ∩ Alkenyls

[ CAS No. 1219454-89-3 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
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Product Details of [ 1219454-89-3 ]

CAS No. :1219454-89-3 MDL No. :MFCD17010193
Formula : C6H5F2NO2S Boiling Point : -
Linear Structure Formula :- InChI Key :YRQNSTAWTLXCEZ-UHFFFAOYSA-N
M.W : 193.17 Pubchem ID :46188280
Synonyms :

Safety of [ 1219454-89-3 ]

Signal Word:Danger Class:6.1
Precautionary Statements:P264-P270-P280-P301+P310+P330-P305+P351+P338-P337+P313-P405-P501 UN#:2811
Hazard Statements:H301-H319 Packing Group:Ⅲ
GHS Pictogram:

Application In Synthesis of [ 1219454-89-3 ]

* 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 [ 1219454-89-3 ]

[ 1219454-89-3 ] Synthesis Path-Downstream   1~28

  • 1
  • [ 1219454-89-3 ]
  • [ 1122-91-4 ]
  • [ 142-08-5 ]
  • [ 84750-93-6 ]
YieldReaction ConditionsOperation in experiment
72% Stage #1: 2-((difluoromethyl)sulfonyl)pyridine; 4-bromo-benzaldehyde With potassium <i>tert</i>-butylate In N,N-dimethyl-formamide at -50 - -40℃; for 0.25h; Inert atmosphere; Stage #2: With hydrogenchloride; water; ammonium chloride In N,N-dimethyl-formamide at -40 - 60℃; Inert atmosphere;
Reference： [1]Zhao, Yanchuan; Huang, Weizhou; Zhu, Lingui; Hu, Jinbo [Organic Letters, 2010, vol. 12, # 7, p. 1444 - 1447]
  • 2
  • 2-((difluoromethyl)thio)pyridine [ No CAS ]
  • [ 1219454-89-3 ]
Reference： [1]Angewandte Chemie - International Edition,2016,vol. 55,p. 2743 - 2747
    Angew. Chem.,2016,vol. 128,p. 2793 - 2797,5
[2]Organic Letters,2010,vol. 12,p. 1444 - 1447
[3]Angewandte Chemie - International Edition,2011,vol. 50,p. 2559 - 2563
[4]Angewandte Chemie - International Edition,2013,vol. 52,p. 3949 - 3952
    Angew. Chem.,2013,vol. 125,p. 4041 - 4044,4
[5]European Journal of Organic Chemistry,2015,vol. 2015,p. 871 - 875
  • 3
  • [ 34683-73-3 ]
  • [ 1219454-89-3 ]
  • [ 1450912-65-8 ]
Reference： [1]Angewandte Chemie - International Edition,2013,vol. 52,p. 3949 - 3952
    Angew. Chem.,2013,vol. 125,p. 4041 - 4044,4
  • 4
  • [ 119-61-9 ]
  • [ 1219454-89-3 ]
  • [ 1638192-40-1 ]
Reference： [1]Chemistry - A European Journal,2014,vol. 20,p. 7803 - 7810
[2]Organic Letters,2016,vol. 18,p. 2766 - 2769
  • 5
  • [ 6185-76-8 ]
  • [ 1219454-89-3 ]
  • [ 1638192-44-5 ]
YieldReaction ConditionsOperation in experiment
64% Stage #1: (4-methoxyphenyl)(4-(trifluoromethyl)phenyl)methanone; 2-((difluoromethyl)sulfonyl)pyridine With lithium hexamethyldisilazane In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; N,N-dimethyl-formamide at -60℃; for 1.08333h; Inert atmosphere; Schlenk technique; Stage #2: With hydrogenchloride In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; water; N,N-dimethyl-formamide at -60 - 130℃; Inert atmosphere; Schlenk technique;
Reference： [1]Gao, Bing; Zhao, Yanchuan; Hu, Mingyou; Ni, Chuanfa; Hu, Jinbo [Chemistry - A European Journal, 2014, vol. 20, # 25, p. 7803 - 7810]
  • 6
  • [ 1219454-89-3 ]
  • [ 80793-25-5 ]
  • [ 1638192-46-7 ]
Reference： [1]Chemistry - A European Journal,2014,vol. 20,p. 7803 - 7810
  • 7
  • [ 638-66-4 ]
  • [ 1219454-89-3 ]
  • [ 66359-73-7 ]
YieldReaction ConditionsOperation in experiment
64% Stage #1: n-Octadecanal; 2-((difluoromethyl)sulfonyl)pyridine With tris(trimethylsilyl)amine; cesium fluoride In N,N-dimethyl-formamide at 20℃; for 8h; Inert atmosphere; Schlenk technique; Stage #2: With hydrogenchloride; ammonium chloride In water; N,N-dimethyl-formamide at 0 - 50℃; for 0.5h; Inert atmosphere; Schlenk technique;
Reference： [1]Gao, Bing; Zhao, Yanchuan; Hu, Mingyou; Ni, Chuanfa; Hu, Jinbo [Chemistry - A European Journal, 2014, vol. 20, # 25, p. 7803 - 7810]
  • 8
  • [ 28856-92-0 ]
  • [ 1219454-89-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: dihydrogen peroxide; ammonium molibdate / water; ethanol / 0 - 20 °C / Inert atmosphere 2: N-fluorobis(benzenesulfon)imide; 1,8-diazabicyclo[5.4.0]undec-7-ene / water; tetrahydrofuran / Inert atmosphere
Reference： [1]Habib, Samuel; Gueyrard, David [European Journal of Organic Chemistry, 2015, vol. 2015, # 4, p. 871 - 875]
  • 9
  • [ 1219454-89-3 ]
  • [ 49647-20-3 ]
  • N-(4-acetylphenyl)-2,2-difluoro-2-(pyridin-2-ylsulfonyl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
68% With sodium t-butanolate In N,N-dimethyl-formamide at -45℃; Inert atmosphere;
Reference： [1]Li, Shan; Peng, Peng; Wei, Jun; Hu, Yongzhou; Hu, Jinbo; Sheng, Rong [Advanced Synthesis and Catalysis, 2015, vol. 357, # 16-17, p. 3429 - 3434]
  • 10
  • [ 1219454-89-3 ]
  • [ 100-52-7 ]
  • 2,2-difluoro-1-phenyl-2-(pyridin-2-ylsulfonyl)ethan-1-ol [ No CAS ]
Reference： [1]Organic Letters,2016,vol. 18,p. 2766 - 2769
[2]Angewandte Chemie - International Edition,2016,vol. 55,p. 2743 - 2747
    Angew. Chem.,2016,vol. 128,p. 2793 - 2797,5
  • 11
  • [ 13909-34-7 ]
  • [ 1219454-89-3 ]
  • N-(2,2-difluoro-1-phenyl-2-(pyridin-2-ylsulfonyl)ethyl)benzenesulfonamide [ No CAS ]
Reference： [1]Organic Letters,2016,vol. 18,p. 2766 - 2769
  • 12
  • [ 1219454-89-3 ]
  • [ 66-99-9 ]
  • 2,2-difluoro-1-(naphthalen-2-yl)-2-(pyridin-2-ylsulfonyl)ethan-1-ol [ No CAS ]
Reference： [1]Organic Letters,2016,vol. 18,p. 2766 - 2769
  • 13
  • [ 1219454-89-3 ]
  • [ 120-14-9 ]
  • 1-(3,4-dimethoxyphenyl)-2,2-difluoro-2-(pyridin-2-ylsulfonyl)ethan-1-ol [ No CAS ]
Reference： [1]Organic Letters,2016,vol. 18,p. 2766 - 2769
  • 14
  • [ 1219454-89-3 ]
  • [ 100-10-7 ]
  • 1-(4-(dimethylamino)phenyl)-2,2-difluoro-2-(pyridin-2-ylsulfonyl)ethan-1-ol [ No CAS ]
Reference： [1]Organic Letters,2016,vol. 18,p. 2766 - 2769
  • 15
  • [ 5381-20-4 ]
  • [ 1219454-89-3 ]
  • 1-(benzo[b]thiophen-3-yl)-2,2-difluoro-2-(pyridin-2-ylsulfonyl)ethan-1-ol [ No CAS ]
Reference： [1]Organic Letters,2016,vol. 18,p. 2766 - 2769
  • 16
  • [ 3481-02-5 ]
  • [ 1219454-89-3 ]
  • 1-cyclopropyl-2,2-difluoro-1-phenyl-2-(pyridin-2-ylsulfonyl)ethan-1-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With lithium hexamethyldisilazane In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane at -98℃; for 0.5h; Schlenk technique; Inert atmosphere;
Reference： [1]Miao, Wenjun; Ni, Chuanfa; Zhao, Yanchuan; Hu, Jinbo [Organic Letters, 2016, vol. 18, # 11, p. 2766 - 2769]
  • 17
  • [ 3695-28-1 ]
  • [ 1219454-89-3 ]
  • C13H17F2NO4S [ No CAS ]
YieldReaction ConditionsOperation in experiment
67% With lithium hexamethyldisilazane; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; at -98℃; for 1.08333h;Inert atmosphere; [0086] As depicted in Scheme 2, to a flask equipped with a magnetic stirrer, HMPA (4 mL) was added under N2 atmosphere to a solution of 2-(difluoromethylsulfonyl)-pyridine (1.5 g, 7.8 mmol, 1.0 equiv.) in THF (50 mL). The reaction mixture was cooled to -98C (CH3OH/liquid nitrogen bath), then 2-methyl-2-(3-iodo)-propyl-1,3-dioxolane (3.15 mL, 0.0194, 2.5 equiv.) was added. A THF solution of LHMDS (2.72 mL, 3.5 equiv.) was added dropwise over 35 minute. After 30 minutes, the reaction mixture was quenched with saturated aqueous NH4C1 solution (2 mL) at -98C. The cold bath was removed and distilled water (1 mL) was added. The mixture was extracted with EtOAc. The combined organic solution was treated with saturated aqueous NaC1 to remove HMPA and dried over Na2SO4. The solvent was removed under reduced pressure to obtain a crude product which was purified by flash column chromatography (EtOAc/Hex) to give a pure product lc (1.67 g, 67% yield) as a light yellow viscous oil. ‘H NMR (400 MHz, CDC13): 8.90-8.84 (m, 1H), 8.17 (dd, I = 7.9, 0.7 Hz, 1H), 8.04 (td, I = 7.8, 1.6 Hz, 1H), 7.67 (ddd, I = 7.7, 4.7, 1.0 Hz, 1H), 4.01-3.85 (m, 2H), 2.58-2.31 (m, 2H), 1.81-1.71 (m, 4H), 1.32 (s, 3H). ‘3C NMR (101 MHz, CDC13) 152.65, 151.45, 139.21, 129.55, 128.55, 125.70 (t), 109.80, 65.10, 38.58, 30.78(t), 24.25, 16.07. MS (ESI+) mlz: 322.
Reference： [1]Bioconjugate Chemistry,2016,vol. 27,p. 1965 - 1971
[2]Patent: WO2016/203478,2016,A1 .Location in patent: Paragraph 0086; 00120
  • 18
  • [ 92-91-1 ]
  • [ 1219454-89-3 ]
  • 1-(1,1-difluoroprop-1-en-2-yl)-4-phenylbenzene [ No CAS ]
Reference： [1]Journal of the American Chemical Society,2017,vol. 139,p. 12855 - 12862
[2]Organic Letters,2019,vol. 21,p. 4585 - 4589
[3]Chemistry - A European Journal,2019,vol. 25,p. 8686 - 8690
  • 19
  • [ 1219454-89-3 ]
  • [ 7029-32-5 ]
  • [ 53731-26-3 ]
YieldReaction ConditionsOperation in experiment
55% With iron(III)-acetylacetonate; N,N,N,N,-tetramethylethylenediamine In tetrahydrofuran at -40 - 20℃; for 2h; Inert atmosphere; Sealed tube;
Reference： [1]Miao, Wenjun; Zhao, Yanchuan; Ni, Chuanfa; Gao, Bing; Zhang, Wei; Hu, Jinbo [Journal of the American Chemical Society, 2018, vol. 140, # 3, p. 880 - 883]
  • 20
  • 8-[2-(4-chlorophenyl)ethyl]-8-azabicyclo[3.2.1]octan-3-one [ No CAS ]
  • [ 1219454-89-3 ]
  • 8-[2-(4-chlorophenyl)ethyl]-3-(difluoromethylene)-8-azabicyclo[3.2.1]octane [ No CAS ]
YieldReaction ConditionsOperation in experiment
30% With potassium tert-butylate; In N,N-dimethyl-formamide; at -50 - 25℃; for 96h;Inert atmosphere; Under argon atmosphere, potassium tert-butoxide (2.2 eq.)dissolved in dry DMF (C 0.9 M)was added to a solution of 8-[2-(4-chlorophenyl)ethyl]-8-azabicyclo[3.2.1]octan-3-one (1, 1.2 eq.) and2-(difluoromethylsulfonyl)pyridine (1 eq.) in dry DMF (C 0.25 M)at 50 C. The reaction mixture was allowed to warm up to 25 C.The mixture was stirred for 4 days at 25 C. Then, the reactionmixture was quenched with aqueous saturated NH4Cl (C 0.5 M),followed by HCl 3M(C 0.5 M). The reaction mixture was allowedto warm up to RT. A solution of NaOH 3M(C 0.5 M) was addedand the product was extracted with DCM (3x). The combinedorganic layers were dried over MgSO4 and concentrated in vacuo.The residuewas purified by flash chromatography (cyHex to cyHex/EtOAc 9/1) to give 8-[2-(4-chlorophenyl)ethyl]-3-(difluoromethylene)-8-azabicyclo[3.2.1]octane (18). Yield: 30%. 1H-NMR(CD2Cl2): δ (ppm) 7.31 (d, J 8.6 Hz, 2H), 7.24 (d, J 8.4 Hz, 2H),3.54-3.46 (m, 2H), 2.97-2.92 (m, 2H), 2.79-2.74 (m, 2H),2.53-2.49 (m, 2H), 2.16 (dd, J = 15.2 Hz, J = 1.1 Hz, 2H), 2.04-1.99(m, 2H), 1.61 (d, J = 8.0 Hz, 2H). 13C-NMR (CD2Cl2): δ (ppm) 153.3 (t,J = 288.3 Hz), 138.3, 131.8, 130.2, 128.4, 81.4 (t, J = 18.9 Hz), 59.2,50.0, 33.8, 29.2, 26.3. HRMS (TOF, ES+) m/z [M+H] calculated forC16H19NF2Cl 298.1174, found 298.1172.
Reference： [1]European Journal of Medicinal Chemistry,2019,vol. 167,p. 426 - 438
  • 21
  • [ 1219454-89-3 ]
  • (1R,4R,7R)-7-bromo-2-(4-methoxybenzyl)-2-azabicyclo[2.2.1]heptane-3,6-dione [ No CAS ]
  • (1R,4R,7R)-7-bromo-6-(difluoromethylene)-2-(4-methoxybenzyl)-2-azabicyclo[2.2.1]heptan-3-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
63% With potassium hexamethylsilazane; In N,N-dimethyl-formamide; at -40 - 20℃; for 1h;Sealed tube; 2-(Difluoromethylsulfonyl)pyridine (20) (2.5 gm, 12.94 mmol, 1.2 equiv) and (1R,4R,7R)-(+)-7-Bromo-2-(4-methoxy-benzyl)-2-azabicyclo[2.2.1]heptane-3,6-dione (5) (3.5 gm, 10.8 mmol, 1 equiv) were combined in a round bottom flask with stir bar to which dimethylformamide (32 ml) was added. The resulting yellow solution was sealed with a serum cap/N2 needle/thermocouple and cooled to -40 C. Potassium bis(trimethylsilyl)amide (KHMDS) solution (15.1 ml, 15.1 mmol, 1.4 equiv) was added keeping the temperature between -40 C. and -35 C. The reaction solution turned a dark orange color as the base was added. The resulting reaction mixture was stirred for I-hour at -40 C. and then allowed to warm to room temperature gradually. The reaction was quenched with saturated NH4Cl solution (10 ml), stirred for 10 minutes, 3M hydrochloric acid (40 ml) was added, stirred for 10 minutes and then the flask contents were heated in a heating bath at 60 C. for 1.5 hours and then cooled to room temperature. Water (35 ml) was added and the reaction was extracted with tert-butyl methyl ether (MTBE) (3×75 ml). The ethereal extracts were combined into one and washed with brine, dried with anhydrous Na2SO4 powder and filtered through a Chem-R-Us plastic sinter funnel to remove the spent drying agent. The filtrate was concentrated (rotary evaporator/vacuum/water bath at 40 C.) to afford a light brown colored oil. The crude product was purified by chromatography on the Biotage on a 100 g silica column, an EtOAc-hexanes gradient [15% (1 CV) 15-75% (7.5 CV) 100% (3 CV)] and fractions collected in 16×100 mm tubes. The product fractions were combined and concentrated (rotary evaporator/vacuum/water bath at 40 C.) to a golden yellow liquid that was pumped down on the vacuum line for several hours, yielding (1R,4R,7R)-(+)-7-bromo-6-(difluoromethylene)-2-(4-methoxybenzyl)-2-azabicyclo[2.2.1]heptane-3-one (6) (2.5 g; 63%)
Reference： [1]Patent: US2019/359555,2019,A1 .Location in patent: Paragraph 0044; 0050; 0133-0135
[2]Journal of the American Chemical Society,2022
  • 22
  • [ 1219454-89-3 ]
  • [ 184429-84-3 ]
  • tert-butyl N-[3,3-difluoro-2-(hydroxymethyl)allyl]carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
20% With potassium tert-butylate; In N,N-dimethyl-formamide; at -50 - 18℃; for 1h; tert-butyl (3,3-difluoro-2-(hydroxymethyl)allyl)carbamate was prepared according to the following procedure. To a stirring solution of tert- butyl (3-((tert-butyldimethylsilyl)oxy)-2- oxopropyl)carbamate (1.0 g, 3.29 mmol) and <strong>[1219454-89-3]2-((difluoromethyl)sulfonyl)pyridine</strong> (0.53 g, 2.75 mmol) in DMF (30 mL) cooled to -50 C was added‘BuOK (0.55 g, 4.95 mmol). The reaction was allowed to warm to 18 C and was stirred for 1 hr. Sat. aq. NH4CI (15 mL) was added followed by 3M HC1 (15 mL). The reaction was stirred for 15 hr at 18 C. The mixture was extracted with EtOAc (3x20 mL), combined organics were dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude residue was purified by automated FCC to afford tert-butyl (3,3-difluoro-2- (hydroxymethyl)allyl)carbamate (150 mg, 20 %) as a yellow oil. ' H NMR (299 MHz, Chloroform-ri) d 4.88 (s, 1H), 4.15 (s, 2H), 3.85 (dd, J= 6.6, 2.0 Hz, 2H), 1.45 (s, 9H).
Reference： [1]Patent: WO2020/69330,2020,A2 .Location in patent: Paragraph 0542
  • 23
  • [ 1219454-89-3 ]
  • [ 184429-84-3 ]
  • tert-butyl N-[2-[[tert-butyl(dimethyl)silyl]oxymethyl]-3,3-difluoroallyl]carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
25.5% With lithium hexamethyldisilazane; In tetrahydrofuran; N,N-dimethyl-formamide; at -70℃; for 0.5h;Inert atmosphere; kinder nitrogen condition, 2.4 g of tert-butyl A-[3 -[tert-butyl (dimethyl )silyl]oxy-2- oxo-propyl]carbamate and 1.0 g of 2-(difluoromethylsulfonyl)pyridine were dissolved in 34.5 mL of Af,A-di methyl form amide and then cooled to -70 C. To the reaction mixture, 10.4 mL of a tetrahydrofuran solution of 1.0 M lithium bis(trimethylsilyl)amide was slowly added dropwise. The resulting solution was stirred at -70 C for 30 minutes and then stirred again by slowly increasing the temperature to -10 C. 20 mL of an ammonium chloride solution was added to the reaction mixture, followed by the addition of 20 mL of a 3 N hydrogen chloride solution. The reaction mixture was extracted with ethyl acetate three times. The extracted organic layer was washed with brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give a yellow liquid residue. The residue was purified with silica gel column chromatography (developing solvent: n-hexane/ethyl acetate = 20/1) to give 446.0 mg of the title compound as a yellow liquid (yield: 25.5 %). ^NMR (CDCb, 400 MHz) d 4.98(s, 1H), 4.20(s, 2H), 3.83(s, 2H), 1.42(s, 9H), 0.89(s, 9H), 0.07(s, 6H)
25.5% With lithium hexamethyldisilazane; In tetrahydrofuran; N,N-dimethyl-formamide; at -70 - -10℃;Inert atmosphere; Under nitrogen condition, 2.4 g of tert-butyl l-[3 -[tert-butyl (dimethyl )silyl]oxy- 2-oxo-propyl]carbamate and 1.0 g of 2-(difluoromethylsulfonyl)pyridine were dissolved in 34.5 mL of /'/,/V-dimethylformamide and then cooled to -70 C. To the reaction mixture, 10.4 mL of a tetrahydrofuran solution of 1.0 M lithium bis(trimethylsilyl)amide was slowly added dropwise. The resulting solution was stirred at -70 C for 30 minutes and then stirred again by slowly increasing the temperature to -10 C. 20 mL of an ammonium chloride solution was added to the reaction mixture, followed by the addition of 20 mL of a 3 N hydrogen chloride solution. The reaction mixture was extracted with ethyl acetate three times. The extracted organic layer was washed with brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give a yellow liquid residue. The residue was purified with silica gel column chromatography (developing solvent: n-hexane/ethyl acetate = 20/1) to give 446 mg of the title compound as a yellow liquid (yield: 25.5 %). -NMR (CDCb, 400 MHz) d 4.98(s, 1H), 4.20(s, 2H), 3.83(s, 2H), 1.42(s, 9H), 0.89(s, 9H), 0.07(s, 6H)
Reference： [1]Patent: WO2020/121261,2020,A1 .Location in patent: Paragraph 0227-0229
[2]Patent: WO2020/121263,2020,A1 .Location in patent: Paragraph 0178-0179
  • 24
  • [ 455-13-0 ]
  • [ 1219454-89-3 ]
  • [ 203065-88-7 ]
YieldReaction ConditionsOperation in experiment
86% With 1,3-bis-(diphenylphosphino)propane; nickel dichloride; zinc In N,N-dimethyl-formamide at 80℃; for 16h; Schlenk technique;
Reference： [1]Miao, Wenjun; Ni, Chuanfa; Xiao, Pan; Jia, Rulong; Zhang, Wei; Hu, Jinbo [Organic Letters, 2021, vol. 23, # 3, p. 711 - 715]
  • 25
  • [ 1219454-89-3 ]
  • [ 64984-08-3 ]
  • 2-(4-(methylsulfonyl)phenyl)pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With 1,3-bis-(diphenylphosphino)propane; nickel dichloride; zinc In N,N-dimethyl-formamide at 80℃; for 16h; Schlenk technique;
Reference： [1]Miao, Wenjun; Ni, Chuanfa; Xiao, Pan; Jia, Rulong; Zhang, Wei; Hu, Jinbo [Organic Letters, 2021, vol. 23, # 3, p. 711 - 715]
  • 26
  • [ 129-81-7 ]
  • [ 1219454-89-3 ]
  • [ 18250-49-2 ]
YieldReaction ConditionsOperation in experiment
55% With 1,3-bis-(diphenylphosphino)propane; nickel dichloride; zinc In N,N-dimethyl-formamide at 80℃; for 16h; Schlenk technique;
Reference： [1]Miao, Wenjun; Ni, Chuanfa; Xiao, Pan; Jia, Rulong; Zhang, Wei; Hu, Jinbo [Organic Letters, 2021, vol. 23, # 3, p. 711 - 715]
  • 27
  • [ 1219454-89-3 ]
  • ethyl (1R,3S)-3-((tert-butoxycarbonyl)amino)-4-oxocyclohexane-1-carboxylate [ No CAS ]
  • ethyl (1R,3S)-3-((tert-butoxycarbonyl)amino)-4-(difluoromethylene)cyclohexane-1-carboxylate [ No CAS ]
Reference： [1]Journal of the American Chemical Society,2021,vol. 143,p. 8193 - 8207
  • 28
  • [ 1219454-89-3 ]
  • 2-methyl-5-(3-trifluoromethylphenyl)-N-(3-(2-oxopropyl)-1,2,4-thiadiazol-5-yl)furan-3-carboxamide [ No CAS ]
  • 2-methyl-5-(3-(trifluoromethyl)phenyl)-N-[3-(3,3-difluoro-2-methylallyl)-1,2,4-thiadiazol-5-yl]furan-3-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
69% With potassium tert-butylate; In N,N-dimethyl-formamide; at -50 - -40℃; for 1h;Inert atmosphere; Under the protection of nitrogen at -50C, add potassium tert-butoxide (49mg, 0.44mmol) in anhydrous DMF (4mL). The solution was added to a solution of compound A-1 (100 mg, 0.24 mmol) and difluoromethyl(2-pyridyl)sulfone (57 mg, 0.29 mmol) in anhydrous DMF (4 mL), and the temperature was raised to -40 C and stirred for 1 h. The reaction was quenched by adding satuYield d ammonium chloride aqueous solution (0.4mL) and 1mol/L dilute hydrochloric acid (0.8mL) to the system, warming the system to room temperature, adding appropriate amount of ethyl acetate, washing with water and satuYield d brine in turn, and the organic layer. After drying and concentrating with anhydrous Na2SO4, the residue was subjected to column chromatography to obtain a pale yellow solid with a yield of 69%.
Reference： [1]Patent: CN113444081,2021,A .Location in patent: Paragraph 0054; 0324-0327

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Related Functional Groups of
[ 1219454-89-3 ]

Sulfones

Chemical Structure| 17075-14-8

[ 17075-14-8 ]

2-(Methylsulfonyl)pyridine

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Related Parent Nucleus of
[ 1219454-89-3 ]

Pyridines

Chemical Structure| 17075-14-8

[ 17075-14-8 ]

2-(Methylsulfonyl)pyridine

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