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Chemistry
Heterocyclic Building Blocks
Quinolines
1-(7-Fluoroquinolin-6-yl)ethan-1-one
Chemistry
Heterocyclic Building Blocks
Quinolines

[ CAS No. 1635407-21-4 ]

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Quality Control of [ 1635407-21-4 ]

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Product Details of [ 1635407-21-4 ]

CAS No. :1635407-21-4 MDL No. :
Formula : C11H8FNO Boiling Point : -
Linear Structure Formula :- InChI Key :FYMRVOJBEHZQES-UHFFFAOYSA-N
M.W :189.19 Pubchem ID :141370334
Synonyms :

Safety of [ 1635407-21-4 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338 UN#:
Hazard Statements:H302-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 1635407-21-4 ]

* 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 [ 1635407-21-4 ]

[ 1635407-21-4 ] Synthesis Path-Downstream   1~26

  • 1
  • [ 656-65-5 ]
  • [ 1635407-21-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium 3-nitrobenzenesulfonate; sulfuric acid / water / 110 - 140 °C 2: bis-triphenylphosphine-palladium(II) chloride / 1,4-dioxane / 4 h / 110 °C
Multi-step reaction with 2 steps 1: sodium 3-nitrobenzenesulfonate; sulfuric acid / water / 140 °C 2: bis-triphenylphosphine-palladium(II) chloride / 1,4-dioxane / 4 h / 110 °C
Multi-step reaction with 2 steps 1.1: sulfuric acid; sodium 3-nitrobenzenesulfonate / water / 120 - 140 °C 2.1: bis-triphenylphosphine-palladium(II) chloride / 1,4-dioxane / 90 °C / Inert atmosphere 2.2: 2 h / 20 °C / Inert atmosphere
Reference： [1]Zhao, Fei; Zhang, Jing; Zhang, Leduo; Hao, Yu; Shi, Chen; Xia, Guangxin; Yu, Jianxin; Liu, Yanjun [Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 18, p. 4281 - 4290]
[2]Zhao, Fei; Zhang, Le-Duo; Hao, Yu; Chen, Na; Bai, Rui; Wang, Yu-Ji; Zhang, Chun-Chun; Li, Gong-Sheng; Hao, Li-Jun; Shi, Chen; Zhang, Jing; Mao, Yu; Fan, Yi; Xia, Guang-Xin; Yu, Jian-Xin; Liu, Yan-Jun [European Journal of Medicinal Chemistry, 2017, vol. 134, p. 147 - 158]
[3]Current Patent Assignee: SHANGHAI PHARMACEUTICALS HOLDING COMPANY LIMITED - CN105968115, 2016, A
  • 2
  • [ 127827-52-5 ]
  • [ 97674-02-7 ]
  • 1-(7-fluoroquinolin-6-yl)ethan-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
99% The starting <strong>[127827-52-5]7-fluoro-6-bromoquinoline</strong> (20.3 g, 0.09 mol) was dissolved in dry dioxane (50 ml) The catalyst Pd (PPh3) 2Cl2 (3.17 g, 4.5 mmol, 0.05 eq) And reagent tributyl (1-ethoxyvinyl) tin (35.87 g, 0.1 mol, 1.1 eq), The reaction was carried out overnight at 90 C under argon. After the temperature was lowered to room temperature, 2eq 10% potassium fluoride aqueous solution was added and stirred at room temperature for 2h, filtered, The filter cake was washed several times with dichloromethane and the filtrate was evaporated to dryness. 2eq of 1N HCl was added and stirred at room temperature for 2h. Add sodium carbonate aqueous solution adjusted to pH 8, dichloromethane extraction, washed with water, After drying, the residue was purified by column chromatography to give 17 g of a yellow solid with a yield of 99%.
87% With bis-triphenylphosphine-palladium(II) chloride; In 1,4-dioxane; at 110℃; for 4h; D-2(2.1 g, 9.3 mmol), 1-ethoxyvinyltri-n-butyltin (3.6 g, 10.1 mmol) and Pd(PPh3)2Cl2(0.3 g, 0.5 mmol) were added to dioxane (20 ml), the mixture was stirred at 110Cfor 4h. After cooled to rt, KF (2.0 g, 21.3 mmol) and water (4 ml) were added,then stirred at rt for 2 h, filtrated and washed with dioxane (5 ml×3). Conc. HCl (2 ml) was added to themother liquor and stirred at rt for 1 h. Then concentrated and added saturatedNa2CO3 aqueous (50 ml), extracted with EtOAc, washed withbrine and dried over anhydrous Na2SO4, then purified byflash column chromatography to afford 1-(7-fluoroquinolin-6-yl)ethan-1-one aspale white solid (D-3, 1.5 g, 87%yield). LC-MS (ESI): [M+H]+=190. 1H NMR (400 MHz, CDCl3)delta 8.99 (dd, J1=4.4 Hz, J2=1.6 Hz, 1H), 8.41 (d, J=8.0Hz, 1H), 8.26 (dd, J1=8.4Hz, J2=1.2 Hz, 1H), 7.81(d, J=12.0 Hz, 1H), 7.44 (dd, J1=8.4Hz, J2=4.4 Hz, 1H), 2.76(d, J=4.8 Hz, 3H).
Reference： [1]Patent: CN105968115,2016,A .Location in patent: Paragraph 0476; 0479-0480; 0560; 0563-0564
[2]Bioorganic and Medicinal Chemistry,2016,vol. 24,p. 4281 - 4290
[3]European Journal of Medicinal Chemistry,2017,vol. 134,p. 147 - 158
  • 3
  • [ 1635407-21-4 ]
  • [ 1266238-22-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: sodium tetrahydroborate / methanol / 1 h / 0 - 20 °C 2: phosphorus tribromide / chloroform / 2 h / 0 °C / Reflux 3: potassium iodide / N,N-dimethyl-formamide / 2 h / 120 °C 4: hydrazine hydrate / ethanol / 2 h / Reflux 5: N-ethyl-N,N-diisopropylamine / 1-methyl-pyrrolidin-2-one / 12 h / 180 °C / Sealed tube
Reference： [1]Zhao, Fei; Zhang, Jing; Zhang, Leduo; Hao, Yu; Shi, Chen; Xia, Guangxin; Yu, Jianxin; Liu, Yanjun [Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 18, p. 4281 - 4290]
  • 4
  • [ 1635407-21-4 ]
  • [ 1635407-58-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: sodium tetrahydroborate / methanol / 1 h / 0 - 20 °C 2: phosphorus tribromide / chloroform / 2 h / 0 °C / Reflux 3: potassium iodide / N,N-dimethyl-formamide / 2 h / 120 °C 4: hydrazine hydrate / ethanol / 2 h / Reflux 5: N-ethyl-N,N-diisopropylamine / 1-methyl-pyrrolidin-2-one / 12 h / 180 °C / Sealed tube 6: 12 h / 150 °C
Reference： [1]Zhao, Fei; Zhang, Jing; Zhang, Leduo; Hao, Yu; Shi, Chen; Xia, Guangxin; Yu, Jianxin; Liu, Yanjun [Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 18, p. 4281 - 4290]
  • 5
  • [ 1635407-21-4 ]
  • [ 1266237-79-9 ]
YieldReaction ConditionsOperation in experiment
74.7% With sodium tetrahydroborate In methanol for 0.5h; Cooling with ice; 3 Synthesis Step 3: Synthesis of 1- (7-fluoro-6-quinolinyl) ethanol (F-4) The starting 7-fluoro-6-quinolinone (20.5 g, 0.108 mol) was dissolved in methanol (100 ml) NaBH4 (3.3 g, 0.087 mol, 0.8 eq) was added in portions under ice-cooling and stirred for 0.5 hour in ice bath. After completion of the reaction, the reaction was quenched with water, evaporated to remove methanol, extracted with ethyl acetate, washed with water, washed with brine, Dried over anhydrous sodium sulfate and purified by column chromatography to obtain 15.4 g of a yellow oil with a yield of 74.7%.
With sodium tetrahydroborate In methanol at 0 - 20℃; for 1h; General procedure: To a solution of C-4 (5.5 g, 29.1 mmol)in MeOH (30 ml), NaBH4 (4.4 g, 115.8 mmol) was added at 0C slowly.The mixture was stirred at rt for 1 h. Water was added and extracted withEtOAc, washed with brine and dried over anhydrous Na2SO4,then concentrated, the intermediate 1-(8-fluoroquinolin-6-yl)ethan-1-ol wasobtained as yellow oil (C-5, 4.9 g,88% yield) which was used directly for the next step. LC-MS (ESI): [M+H]+=192.1H NMR (400 MHz, CDCl3) δ 8.87-8.85 (m, 1H), 8.10 (d, J=8.4 Hz, 1H), 7.55 (s, 1H), 7.44-7.40(m, 2H), 5.06 (q, J=6.4 Hz, 1H), 3.18(brs, 1H), 1.56 (d, J=6.4 Hz, 3H).
With sodium tetrahydroborate In methanol at 20℃; for 1h;
Reference： [1]Current Patent Assignee: SHANGHAI PHARMACEUTICALS HOLDING COMPANY LIMITED - CN105968115, 2016, A Location in patent: Paragraph 0560; 0565-0566
[2]Zhao, Fei; Zhang, Jing; Zhang, Leduo; Hao, Yu; Shi, Chen; Xia, Guangxin; Yu, Jianxin; Liu, Yanjun [Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 18, p. 4281 - 4290]
[3]Zhao, Fei; Zhang, Le-Duo; Hao, Yu; Chen, Na; Bai, Rui; Wang, Yu-Ji; Zhang, Chun-Chun; Li, Gong-Sheng; Hao, Li-Jun; Shi, Chen; Zhang, Jing; Mao, Yu; Fan, Yi; Xia, Guang-Xin; Yu, Jian-Xin; Liu, Yan-Jun [European Journal of Medicinal Chemistry, 2017, vol. 134, p. 147 - 158]
  • 6
  • [ 1635407-21-4 ]
  • [ 1635407-22-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium tetrahydroborate / methanol / 1 h / 0 - 20 °C 2: phosphorus tribromide / chloroform / 2 h / 0 °C / Reflux
Multi-step reaction with 2 steps 1: sodium tetrahydroborate / methanol / 1 h / 20 °C 2: phosphorus tribromide / chloroform / 2 h / Reflux
Reference： [1]Zhao, Fei; Zhang, Jing; Zhang, Leduo; Hao, Yu; Shi, Chen; Xia, Guangxin; Yu, Jianxin; Liu, Yanjun [Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 18, p. 4281 - 4290]
[2]Zhao, Fei; Zhang, Le-Duo; Hao, Yu; Chen, Na; Bai, Rui; Wang, Yu-Ji; Zhang, Chun-Chun; Li, Gong-Sheng; Hao, Li-Jun; Shi, Chen; Zhang, Jing; Mao, Yu; Fan, Yi; Xia, Guang-Xin; Yu, Jian-Xin; Liu, Yan-Jun [European Journal of Medicinal Chemistry, 2017, vol. 134, p. 147 - 158]
  • 7
  • [ 1635407-21-4 ]
  • [ 1266237-80-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: sodium tetrahydroborate / methanol / 1 h / 0 - 20 °C 2: phosphorus tribromide / chloroform / 2 h / 0 °C / Reflux 3: potassium iodide / N,N-dimethyl-formamide / 2 h / 120 °C
Multi-step reaction with 3 steps 1: sodium tetrahydroborate / methanol / 1 h / 20 °C 2: phosphorus tribromide / chloroform / 2 h / Reflux 3: potassium iodide / N,N-dimethyl-formamide / 12 h / 120 °C
Reference： [1]Zhao, Fei; Zhang, Jing; Zhang, Leduo; Hao, Yu; Shi, Chen; Xia, Guangxin; Yu, Jianxin; Liu, Yanjun [Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 18, p. 4281 - 4290]
[2]Zhao, Fei; Zhang, Le-Duo; Hao, Yu; Chen, Na; Bai, Rui; Wang, Yu-Ji; Zhang, Chun-Chun; Li, Gong-Sheng; Hao, Li-Jun; Shi, Chen; Zhang, Jing; Mao, Yu; Fan, Yi; Xia, Guang-Xin; Yu, Jian-Xin; Liu, Yan-Jun [European Journal of Medicinal Chemistry, 2017, vol. 134, p. 147 - 158]
  • 8
  • [ 1635407-21-4 ]
  • [ 1635405-90-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1: sodium tetrahydroborate / methanol / 1 h / 0 - 20 °C 2: phosphorus tribromide / chloroform / 2 h / 0 °C / Reflux 3: potassium iodide / N,N-dimethyl-formamide / 2 h / 120 °C 4: hydrazine hydrate / ethanol / 2 h / Reflux 5: N-ethyl-N,N-diisopropylamine / 1-methyl-pyrrolidin-2-one / 12 h / 180 °C / Sealed tube 6: 12 h / 150 °C 7: 1,1'-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex; potassium carbonate / water; 1,4-dioxane / 4 h / 110 °C / Inert atmosphere
Reference： [1]Zhao, Fei; Zhang, Jing; Zhang, Leduo; Hao, Yu; Shi, Chen; Xia, Guangxin; Yu, Jianxin; Liu, Yanjun [Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 18, p. 4281 - 4290]
  • 9
  • [ 1635407-21-4 ]
  • [ 1635405-92-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1: sodium tetrahydroborate / methanol / 1 h / 0 - 20 °C 2: phosphorus tribromide / chloroform / 2 h / 0 °C / Reflux 3: potassium iodide / N,N-dimethyl-formamide / 2 h / 120 °C 4: hydrazine hydrate / ethanol / 2 h / Reflux 5: N-ethyl-N,N-diisopropylamine / 1-methyl-pyrrolidin-2-one / 12 h / 180 °C / Sealed tube 6: 12 h / 150 °C 7: 1,1'-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex; potassium carbonate / water; 1,4-dioxane / 4 h / 110 °C / Inert atmosphere
Reference： [1]Zhao, Fei; Zhang, Jing; Zhang, Leduo; Hao, Yu; Shi, Chen; Xia, Guangxin; Yu, Jianxin; Liu, Yanjun [Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 18, p. 4281 - 4290]
  • 10
  • [ 1635407-21-4 ]
  • [ 1635405-95-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1: sodium tetrahydroborate / methanol / 1 h / 0 - 20 °C 2: phosphorus tribromide / chloroform / 2 h / 0 °C / Reflux 3: potassium iodide / N,N-dimethyl-formamide / 2 h / 120 °C 4: hydrazine hydrate / ethanol / 2 h / Reflux 5: N-ethyl-N,N-diisopropylamine / 1-methyl-pyrrolidin-2-one / 12 h / 180 °C / Sealed tube 6: 12 h / 150 °C 7: 1,1'-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex; potassium carbonate / water; 1,4-dioxane / 4 h / 110 °C / Inert atmosphere
Reference： [1]Zhao, Fei; Zhang, Jing; Zhang, Leduo; Hao, Yu; Shi, Chen; Xia, Guangxin; Yu, Jianxin; Liu, Yanjun [Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 18, p. 4281 - 4290]
  • 11
  • [ 1635407-21-4 ]
  • [ 1635405-94-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1: sodium tetrahydroborate / methanol / 1 h / 0 - 20 °C 2: phosphorus tribromide / chloroform / 2 h / 0 °C / Reflux 3: potassium iodide / N,N-dimethyl-formamide / 2 h / 120 °C 4: hydrazine hydrate / ethanol / 2 h / Reflux 5: N-ethyl-N,N-diisopropylamine / 1-methyl-pyrrolidin-2-one / 12 h / 180 °C / Sealed tube 6: 12 h / 150 °C 7: 1,1'-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex; potassium carbonate / water; 1,4-dioxane / 4 h / 110 °C / Inert atmosphere
Reference： [1]Zhao, Fei; Zhang, Jing; Zhang, Leduo; Hao, Yu; Shi, Chen; Xia, Guangxin; Yu, Jianxin; Liu, Yanjun [Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 18, p. 4281 - 4290]
  • 12
  • [ 1635407-21-4 ]
  • [ 1635405-93-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1: sodium tetrahydroborate / methanol / 1 h / 0 - 20 °C 2: phosphorus tribromide / chloroform / 2 h / 0 °C / Reflux 3: potassium iodide / N,N-dimethyl-formamide / 2 h / 120 °C 4: hydrazine hydrate / ethanol / 2 h / Reflux 5: N-ethyl-N,N-diisopropylamine / 1-methyl-pyrrolidin-2-one / 12 h / 180 °C / Sealed tube 6: 12 h / 150 °C 7: 1,1'-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex; potassium carbonate / water; 1,4-dioxane / 4 h / 110 °C / Inert atmosphere
Reference： [1]Zhao, Fei; Zhang, Jing; Zhang, Leduo; Hao, Yu; Shi, Chen; Xia, Guangxin; Yu, Jianxin; Liu, Yanjun [Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 18, p. 4281 - 4290]
  • 13
  • [ 1635407-21-4 ]
  • [ 1635405-97-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1: sodium tetrahydroborate / methanol / 1 h / 0 - 20 °C 2: phosphorus tribromide / chloroform / 2 h / 0 °C / Reflux 3: potassium iodide / N,N-dimethyl-formamide / 2 h / 120 °C 4: hydrazine hydrate / ethanol / 2 h / Reflux 5: N-ethyl-N,N-diisopropylamine / 1-methyl-pyrrolidin-2-one / 12 h / 180 °C / Sealed tube 6: 12 h / 150 °C 7: 1,1'-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex; potassium carbonate / water; 1,4-dioxane / 4 h / 110 °C / Inert atmosphere
Reference： [1]Zhao, Fei; Zhang, Jing; Zhang, Leduo; Hao, Yu; Shi, Chen; Xia, Guangxin; Yu, Jianxin; Liu, Yanjun [Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 18, p. 4281 - 4290]
  • 14
  • [ 1635407-21-4 ]
  • [ 1635405-99-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1: sodium tetrahydroborate / methanol / 1 h / 0 - 20 °C 2: phosphorus tribromide / chloroform / 2 h / 0 °C / Reflux 3: potassium iodide / N,N-dimethyl-formamide / 2 h / 120 °C 4: hydrazine hydrate / ethanol / 2 h / Reflux 5: N-ethyl-N,N-diisopropylamine / 1-methyl-pyrrolidin-2-one / 12 h / 180 °C / Sealed tube 6: 12 h / 150 °C 7: 1,1'-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex; potassium carbonate / water; 1,4-dioxane / 4 h / 110 °C / Inert atmosphere
Reference： [1]Zhao, Fei; Zhang, Jing; Zhang, Leduo; Hao, Yu; Shi, Chen; Xia, Guangxin; Yu, Jianxin; Liu, Yanjun [Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 18, p. 4281 - 4290]
  • 15
  • [ 1635407-21-4 ]
  • [ 1635405-98-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1: sodium tetrahydroborate / methanol / 1 h / 0 - 20 °C 2: phosphorus tribromide / chloroform / 2 h / 0 °C / Reflux 3: potassium iodide / N,N-dimethyl-formamide / 2 h / 120 °C 4: hydrazine hydrate / ethanol / 2 h / Reflux 5: N-ethyl-N,N-diisopropylamine / 1-methyl-pyrrolidin-2-one / 12 h / 180 °C / Sealed tube 6: 12 h / 150 °C 7: 1,1'-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex; potassium carbonate / water; 1,4-dioxane / 4 h / 110 °C / Inert atmosphere
Reference： [1]Zhao, Fei; Zhang, Jing; Zhang, Leduo; Hao, Yu; Shi, Chen; Xia, Guangxin; Yu, Jianxin; Liu, Yanjun [Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 18, p. 4281 - 4290]
  • 16
  • [ 1635407-21-4 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1: sodium tetrahydroborate / methanol / 1 h / 0 - 20 °C 2: phosphorus tribromide / chloroform / 2 h / 0 °C / Reflux 3: potassium iodide / N,N-dimethyl-formamide / 2 h / 120 °C 4: hydrazine hydrate / ethanol / 2 h / Reflux 5: N-ethyl-N,N-diisopropylamine / 1-methyl-pyrrolidin-2-one / 12 h / 180 °C / Sealed tube 6: 12 h / 150 °C 7: 1,1'-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex; potassium carbonate / water; 1,4-dioxane / 4 h / 110 °C / Inert atmosphere
Reference： [1]Zhao, Fei; Zhang, Jing; Zhang, Leduo; Hao, Yu; Shi, Chen; Xia, Guangxin; Yu, Jianxin; Liu, Yanjun [Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 18, p. 4281 - 4290]
  • 17
  • [ 1635407-21-4 ]
  • [ 1266237-81-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: sodium tetrahydroborate / methanol / 1 h / 0 - 20 °C 2: phosphorus tribromide / chloroform / 2 h / 0 °C / Reflux 3: potassium iodide / N,N-dimethyl-formamide / 2 h / 120 °C 4: hydrazine hydrate / ethanol / 2 h / Reflux
Reference： [1]Zhao, Fei; Zhang, Jing; Zhang, Leduo; Hao, Yu; Shi, Chen; Xia, Guangxin; Yu, Jianxin; Liu, Yanjun [Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 18, p. 4281 - 4290]
  • 18
  • [ 1635407-21-4 ]
  • [ 1635407-42-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: sodium tetrahydroborate / methanol / 1 h / 20 °C 2: phosphorus tribromide / chloroform / 2 h / Reflux 3: potassium iodide / N,N-dimethyl-formamide / 12 h / 120 °C 4: pyridine; bromine / tetrachloromethane / 70 °C 5: 1,1'-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex; potassium carbonate / water; 1,4-dioxane / 3 h / 110 °C / Sealed tube 6: hydrazine hydrate / ethanol / 2 h / Reflux
Reference： [1]Zhao, Fei; Zhang, Le-Duo; Hao, Yu; Chen, Na; Bai, Rui; Wang, Yu-Ji; Zhang, Chun-Chun; Li, Gong-Sheng; Hao, Li-Jun; Shi, Chen; Zhang, Jing; Mao, Yu; Fan, Yi; Xia, Guang-Xin; Yu, Jian-Xin; Liu, Yan-Jun [European Journal of Medicinal Chemistry, 2017, vol. 134, p. 147 - 158]
  • 19
  • [ 1635407-21-4 ]
  • [ 2097510-07-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: sodium tetrahydroborate / methanol / 1 h / 20 °C 2: phosphorus tribromide / chloroform / 2 h / Reflux 3: potassium iodide / N,N-dimethyl-formamide / 12 h / 120 °C 4: pyridine; bromine / tetrachloromethane / 70 °C 5: 1,1'-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex; potassium carbonate / water; 1,4-dioxane / 3 h / 110 °C / Sealed tube 6: hydrazine hydrate / ethanol / 2 h / Reflux
Reference： [1]Zhao, Fei; Zhang, Le-Duo; Hao, Yu; Chen, Na; Bai, Rui; Wang, Yu-Ji; Zhang, Chun-Chun; Li, Gong-Sheng; Hao, Li-Jun; Shi, Chen; Zhang, Jing; Mao, Yu; Fan, Yi; Xia, Guang-Xin; Yu, Jian-Xin; Liu, Yan-Jun [European Journal of Medicinal Chemistry, 2017, vol. 134, p. 147 - 158]
  • 20
  • [ 1635407-21-4 ]
  • [ 1635407-67-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1: sodium tetrahydroborate / methanol / 1 h / 20 °C 2: phosphorus tribromide / chloroform / 2 h / Reflux 3: potassium iodide / N,N-dimethyl-formamide / 12 h / 120 °C 4: pyridine; bromine / tetrachloromethane / 70 °C 5: 1,1'-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex; potassium carbonate / water; 1,4-dioxane / 3 h / 110 °C / Sealed tube 6: hydrazine hydrate / ethanol / 2 h / Reflux 7: N-ethyl-N,N-diisopropylamine / 1-methyl-pyrrolidin-2-one / 180 °C / Sealed tube
Reference： [1]Zhao, Fei; Zhang, Le-Duo; Hao, Yu; Chen, Na; Bai, Rui; Wang, Yu-Ji; Zhang, Chun-Chun; Li, Gong-Sheng; Hao, Li-Jun; Shi, Chen; Zhang, Jing; Mao, Yu; Fan, Yi; Xia, Guang-Xin; Yu, Jian-Xin; Liu, Yan-Jun [European Journal of Medicinal Chemistry, 2017, vol. 134, p. 147 - 158]
  • 21
  • [ 1635407-21-4 ]
  • [ 2097516-10-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1: sodium tetrahydroborate / methanol / 1 h / 20 °C 2: phosphorus tribromide / chloroform / 2 h / Reflux 3: potassium iodide / N,N-dimethyl-formamide / 12 h / 120 °C 4: pyridine; bromine / tetrachloromethane / 70 °C 5: 1,1'-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex; potassium carbonate / water; 1,4-dioxane / 3 h / 110 °C / Sealed tube 6: hydrazine hydrate / ethanol / 2 h / Reflux 7: N-ethyl-N,N-diisopropylamine / 1-methyl-pyrrolidin-2-one / 180 °C / Sealed tube
Reference： [1]Zhao, Fei; Zhang, Le-Duo; Hao, Yu; Chen, Na; Bai, Rui; Wang, Yu-Ji; Zhang, Chun-Chun; Li, Gong-Sheng; Hao, Li-Jun; Shi, Chen; Zhang, Jing; Mao, Yu; Fan, Yi; Xia, Guang-Xin; Yu, Jian-Xin; Liu, Yan-Jun [European Journal of Medicinal Chemistry, 2017, vol. 134, p. 147 - 158]
  • 22
  • [ 1635407-21-4 ]
  • [ 1635407-68-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1: sodium tetrahydroborate / methanol / 1 h / 20 °C 2: phosphorus tribromide / chloroform / 2 h / Reflux 3: potassium iodide / N,N-dimethyl-formamide / 12 h / 120 °C 4: pyridine; bromine / tetrachloromethane / 70 °C 5: 1,1'-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex; potassium carbonate / water; 1,4-dioxane / 3 h / 110 °C / Sealed tube 6: hydrazine hydrate / ethanol / 2 h / Reflux 7: N-ethyl-N,N-diisopropylamine / 1-methyl-pyrrolidin-2-one / 180 °C / Sealed tube 8: isopentyl nitrite / N,N-dimethyl-formamide / 2 h / 80 °C
Reference： [1]Zhao, Fei; Zhang, Le-Duo; Hao, Yu; Chen, Na; Bai, Rui; Wang, Yu-Ji; Zhang, Chun-Chun; Li, Gong-Sheng; Hao, Li-Jun; Shi, Chen; Zhang, Jing; Mao, Yu; Fan, Yi; Xia, Guang-Xin; Yu, Jian-Xin; Liu, Yan-Jun [European Journal of Medicinal Chemistry, 2017, vol. 134, p. 147 - 158]
  • 23
  • [ 1635407-21-4 ]
  • [ 2097518-24-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1: sodium tetrahydroborate / methanol / 1 h / 20 °C 2: phosphorus tribromide / chloroform / 2 h / Reflux 3: potassium iodide / N,N-dimethyl-formamide / 12 h / 120 °C 4: pyridine; bromine / tetrachloromethane / 70 °C 5: 1,1'-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex; potassium carbonate / water; 1,4-dioxane / 3 h / 110 °C / Sealed tube 6: hydrazine hydrate / ethanol / 2 h / Reflux 7: N-ethyl-N,N-diisopropylamine / 1-methyl-pyrrolidin-2-one / 180 °C / Sealed tube 8: isopentyl nitrite / N,N-dimethyl-formamide / 2 h / 80 °C
Reference： [1]Zhao, Fei; Zhang, Le-Duo; Hao, Yu; Chen, Na; Bai, Rui; Wang, Yu-Ji; Zhang, Chun-Chun; Li, Gong-Sheng; Hao, Li-Jun; Shi, Chen; Zhang, Jing; Mao, Yu; Fan, Yi; Xia, Guang-Xin; Yu, Jian-Xin; Liu, Yan-Jun [European Journal of Medicinal Chemistry, 2017, vol. 134, p. 147 - 158]
  • 24
  • [ 1635407-21-4 ]
  • [ 1635407-40-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: sodium tetrahydroborate / methanol / 1 h / 20 °C 2: phosphorus tribromide / chloroform / 2 h / Reflux 3: potassium iodide / N,N-dimethyl-formamide / 12 h / 120 °C 4: pyridine; bromine / tetrachloromethane / 70 °C
Reference： [1]Zhao, Fei; Zhang, Le-Duo; Hao, Yu; Chen, Na; Bai, Rui; Wang, Yu-Ji; Zhang, Chun-Chun; Li, Gong-Sheng; Hao, Li-Jun; Shi, Chen; Zhang, Jing; Mao, Yu; Fan, Yi; Xia, Guang-Xin; Yu, Jian-Xin; Liu, Yan-Jun [European Journal of Medicinal Chemistry, 2017, vol. 134, p. 147 - 158]
  • 25
  • [ 1635407-21-4 ]
  • [ 1635407-41-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: sodium tetrahydroborate / methanol / 1 h / 20 °C 2: phosphorus tribromide / chloroform / 2 h / Reflux 3: potassium iodide / N,N-dimethyl-formamide / 12 h / 120 °C 4: pyridine; bromine / tetrachloromethane / 70 °C 5: 1,1'-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex; potassium carbonate / water; 1,4-dioxane / 3 h / 110 °C / Sealed tube
Reference： [1]Zhao, Fei; Zhang, Le-Duo; Hao, Yu; Chen, Na; Bai, Rui; Wang, Yu-Ji; Zhang, Chun-Chun; Li, Gong-Sheng; Hao, Li-Jun; Shi, Chen; Zhang, Jing; Mao, Yu; Fan, Yi; Xia, Guang-Xin; Yu, Jian-Xin; Liu, Yan-Jun [European Journal of Medicinal Chemistry, 2017, vol. 134, p. 147 - 158]
  • 26
  • [ 1635407-21-4 ]
  • [ 2097514-74-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: sodium tetrahydroborate / methanol / 1 h / 20 °C 2: phosphorus tribromide / chloroform / 2 h / Reflux 3: potassium iodide / N,N-dimethyl-formamide / 12 h / 120 °C 4: pyridine; bromine / tetrachloromethane / 70 °C 5: 1,1'-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex; potassium carbonate / water; 1,4-dioxane / 3 h / 110 °C / Sealed tube
Reference： [1]Zhao, Fei; Zhang, Le-Duo; Hao, Yu; Chen, Na; Bai, Rui; Wang, Yu-Ji; Zhang, Chun-Chun; Li, Gong-Sheng; Hao, Li-Jun; Shi, Chen; Zhang, Jing; Mao, Yu; Fan, Yi; Xia, Guang-Xin; Yu, Jian-Xin; Liu, Yan-Jun [European Journal of Medicinal Chemistry, 2017, vol. 134, p. 147 - 158]

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