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Product Details of [ 858972-17-5 ]

CAS No. :858972-17-5 MDL No. :MFCD16620934
Formula : C10H12FNO2 Boiling Point : -
Linear Structure Formula :- InChI Key :GQVVSIVOVOFWBK-UHFFFAOYSA-N
M.W : 197.21 Pubchem ID :68983893
Synonyms :

Safety of [ 858972-17-5 ]

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 [ 858972-17-5 ]

* 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 [ 858972-17-5 ]

[ 858972-17-5 ] Synthesis Path-Downstream   1~21

  • 1
  • [ 858972-16-4 ]
  • [ 858972-17-5 ]
YieldReaction ConditionsOperation in experiment
94% With hydrogen In ethanol at 20℃; atmospheric pressure;
177 g With palladium 10% on activated carbon; hydrogen at 40℃; for 16h; 1.2; 2.2; 8.2 2) Reduction reaction The crude product obtained in step 1) was dissolved in 1.2 L of ethanol, 1 g of 10% palladium-carbon was added, and hydrogen was replaced three times, and hydrogenated at 40 ° C under normal pressure for 16 hours. The nitrogen was replaced and the palladium on carbon was filtered off. Desolvation under reduced pressure gave ethyl 3-amino-4-fluorophenylacetate, 177 g, 90% yield in two steps, and 98.7% purity by HPLC.
  • 2
  • [ 858972-17-5 ]
  • [ 858972-19-7 ]
YieldReaction ConditionsOperation in experiment
95% With sodium azide; trifluoroacetic acid; sodium nitrite at 0℃; for 0.166667h;
  • 3
  • [ 587-88-2 ]
  • [ 858972-17-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 79 percent / H2SO4; HNO3 / 0.58 h / 0 °C 2: 94 percent / hydrogen / Pd/C / ethanol / 20 °C / atmospheric pressure
  • 4
  • [ 405-50-5 ]
  • [ 858972-17-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 98 percent / H2SO4 / 2.5 h / 80 °C 2: 79 percent / H2SO4; HNO3 / 0.58 h / 0 °C 3: 94 percent / hydrogen / Pd/C / ethanol / 20 °C / atmospheric pressure
  • 5
  • [ 858972-17-5 ]
  • 3-(3-azido-4-fluorophenyl)-2-oxopropanal [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1: 95 percent / NaNO2; NaN3; trifluoroacetic acid / 0.17 h / 0 °C 2: 93 percent / potassium hydroxide / diethyl ether; ethanol / 0 - 20 °C 3: thionyl chloride / 1.5 h / Heating 4: 2.23 g / diethyl ether / 0 °C 5: 93 percent / acetic acid; HBr / H2O / 0 - 20 °C 6: CH2Cl2 / 2 h / 70 °C 7: 2.19 g / sodium hydroxide / H2O / 0 - 20 °C / sonication 8: H2SO4 / H2O / 0 - 20 °C
  • 6
  • [ 858972-17-5 ]
  • [ 858972-21-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 95 percent / NaNO2; NaN3; trifluoroacetic acid / 0.17 h / 0 °C 2: 93 percent / potassium hydroxide / diethyl ether; ethanol / 0 - 20 °C 3: thionyl chloride / 1.5 h / Heating 4: 2.23 g / diethyl ether / 0 °C
  • 7
  • [ 858972-17-5 ]
  • [ 858972-22-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 95 percent / NaNO2; NaN3; trifluoroacetic acid / 0.17 h / 0 °C 2: 93 percent / potassium hydroxide / diethyl ether; ethanol / 0 - 20 °C 3: thionyl chloride / 1.5 h / Heating 4: 2.23 g / diethyl ether / 0 °C 5: 93 percent / acetic acid; HBr / H2O / 0 - 20 °C
  • 8
  • [ 858972-17-5 ]
  • N-(N',N'-dimethylaminophenyl)-N-3-(3-azido-4-fluorophenyl)-2-oxopropanimine oxide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1: 95 percent / NaNO2; NaN3; trifluoroacetic acid / 0.17 h / 0 °C 2: 93 percent / potassium hydroxide / diethyl ether; ethanol / 0 - 20 °C 3: thionyl chloride / 1.5 h / Heating 4: 2.23 g / diethyl ether / 0 °C 5: 93 percent / acetic acid; HBr / H2O / 0 - 20 °C 6: CH2Cl2 / 2 h / 70 °C 7: 2.19 g / sodium hydroxide / H2O / 0 - 20 °C / sonication
  • 9
  • [ 858972-17-5 ]
  • 8-benzyl-2-(3-azido-4-fluorobenzylidene)-6-(4-hydroxyphenyl)-2,3-dihydroimidazo[1,2-a]pyrazin-3-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 10 steps 1: 95 percent / NaNO2; NaN3; trifluoroacetic acid / 0.17 h / 0 °C 2: 93 percent / potassium hydroxide / diethyl ether; ethanol / 0 - 20 °C 3: thionyl chloride / 1.5 h / Heating 4: 2.23 g / diethyl ether / 0 °C 5: 93 percent / acetic acid; HBr / H2O / 0 - 20 °C 6: CH2Cl2 / 2 h / 70 °C 7: 2.19 g / sodium hydroxide / H2O / 0 - 20 °C / sonication 8: H2SO4 / H2O / 0 - 20 °C 9: HCl / H2O; dioxane / 3.5 h / 80 °C 10: 45 mg / manganese(II) oxide / diethyl ether; ethanol / 0 - 20 °C
  • 10
  • [ 858972-17-5 ]
  • [ 858972-25-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 9 steps 1: 95 percent / NaNO2; NaN3; trifluoroacetic acid / 0.17 h / 0 °C 2: 93 percent / potassium hydroxide / diethyl ether; ethanol / 0 - 20 °C 3: thionyl chloride / 1.5 h / Heating 4: 2.23 g / diethyl ether / 0 °C 5: 93 percent / acetic acid; HBr / H2O / 0 - 20 °C 6: CH2Cl2 / 2 h / 70 °C 7: 2.19 g / sodium hydroxide / H2O / 0 - 20 °C / sonication 8: H2SO4 / H2O / 0 - 20 °C 9: HCl / H2O; dioxane / 3.5 h / 80 °C
  • 11
  • [ 858972-17-5 ]
  • 1-[3-(3-azido-4-fluoro-phenyl)-2-oxo-propyl]-pyridinium; bromide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: 95 percent / NaNO2; NaN3; trifluoroacetic acid / 0.17 h / 0 °C 2: 93 percent / potassium hydroxide / diethyl ether; ethanol / 0 - 20 °C 3: thionyl chloride / 1.5 h / Heating 4: 2.23 g / diethyl ether / 0 °C 5: 93 percent / acetic acid; HBr / H2O / 0 - 20 °C 6: CH2Cl2 / 2 h / 70 °C
  • 12
  • [ 858972-17-5 ]
  • C28H19(2)H4F4N4O3(1+) [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 11 steps 1: 95 percent / NaNO2; NaN3; trifluoroacetic acid / 0.17 h / 0 °C 2: 93 percent / potassium hydroxide / diethyl ether; ethanol / 0 - 20 °C 3: thionyl chloride / 1.5 h / Heating 4: 2.23 g / diethyl ether / 0 °C 5: 93 percent / acetic acid; HBr / H2O / 0 - 20 °C 6: CH2Cl2 / 2 h / 70 °C 7: 2.19 g / sodium hydroxide / H2O / 0 - 20 °C / sonication 8: H2SO4 / H2O / 0 - 20 °C 9: HCl / H2O; dioxane / 3.5 h / 80 °C 10: 0.25 h / 20 °C / Irradiation 11: CH3OD; CH3COOD
  • 13
  • [ 858972-17-5 ]
  • C28H22F4N4O3*H(1+) [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 10 steps 1: 95 percent / NaNO2; NaN3; trifluoroacetic acid / 0.17 h / 0 °C 2: 93 percent / potassium hydroxide / diethyl ether; ethanol / 0 - 20 °C 3: thionyl chloride / 1.5 h / Heating 4: 2.23 g / diethyl ether / 0 °C 5: 93 percent / acetic acid; HBr / H2O / 0 - 20 °C 6: CH2Cl2 / 2 h / 70 °C 7: 2.19 g / sodium hydroxide / H2O / 0 - 20 °C / sonication 8: H2SO4 / H2O / 0 - 20 °C 9: HCl / H2O; dioxane / 3.5 h / 80 °C 10: 0.25 h / 20 °C / Irradiation
  • 14
  • [ 858972-17-5 ]
  • (3-azido-4-fluoro-phenyl)-acetyl chloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 95 percent / NaNO2; NaN3; trifluoroacetic acid / 0.17 h / 0 °C 2: 93 percent / potassium hydroxide / diethyl ether; ethanol / 0 - 20 °C 3: thionyl chloride / 1.5 h / Heating
  • 15
  • [ 858972-17-5 ]
  • [ 858972-20-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 95 percent / NaNO2; NaN3; trifluoroacetic acid / 0.17 h / 0 °C 2: 93 percent / potassium hydroxide / diethyl ether; ethanol / 0 - 20 °C
  • 16
  • [ 858972-17-5 ]
  • [ 1012879-35-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: potassium fluoride; aluminum oxide / N,N-dimethyl acetamide / 1 h / 20 °C 2: 4 h / 180 °C / Inert atmosphere 3: trifluoroacetic acid / dichloromethane / Reflux
  • 17
  • [ 858972-17-5 ]
  • 3-(3-amino-4-fluorophenyl)-1-isopropyl-7-[(4-methoxybenzyl)-methyl-amino]-1H-[1,6]naphthyridin-2-one hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium fluoride; aluminum oxide / N,N-dimethyl acetamide / 1 h / 20 °C 2: 4 h / 180 °C / Inert atmosphere
  • 18
  • [ 959163-01-0 ]
  • [ 858972-17-5 ]
  • [ 1012878-78-2 ]
YieldReaction ConditionsOperation in experiment
68% With potassium carbonate In N,N-dimethyl-formamide at 80℃; A38 Example A38 A solution of Example B1 (6.0 g, 0.033 mol), ethyl 2-(3-amino-4-fluorophenyl)acetate (6.4 g, 0.033 mol) and K2CO3 (9.17 g, 0.066 mol) in DMF (100 mL) was heated to 80° C. overnight. The reaction mixture was poured into the water and extracted with EtOAc (3*). The combined extracts were washed with brine (3*), dried (MgSO4), concentrated in vacuo and purified by chromatography to provide 3-(3-amino-4-fluorophenyl)-7-chloro-1-ethyl-1,6-naphthyridin-2(1H)-one (7.0 g, 68% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.75 (s, 1H), 8.07 (s, 1H), 7.67 (s, 1H), 7.13 (dd, J=8.8, 2.0 Hz, 1H), 7.02 (dd, J=11.6, 8.4 Hz, 1H), 6.80 (m, 1H), 5.20 (s, 2H), 4.25 (q, J=6.8 Hz, 2H), 1.19 (t, J=6.8 Hz, 3H); MS (ESI) m/z: 318.2 [M+H]+.
68% With potassium carbonate In N,N-dimethyl-formamide at 80℃; A38 Example A38: A solution of Example B1 (6.0 g, 0.033 mol), ethyl2-(3-amino-4-fluorophenyl)acetate (6.4 g, 0.033 mol) and K2C03 (9.17 g, 0.066 mol) in DMF (100 mL)was heated to 80°C overnight. The reaction mixture was poured into the water and extractedwith EtOAc (3x). The combined extracts were washed with brine (3x), dried (MgS04),concentrated in vacuo and purified by chromatography to provide 3-(3-amino-4-fluorophenyl)-7 -chloro-1-ethyl-1 ,6-naphthyridin-2(1H)-one (7 .0 g, 68% yield). 1 H NMR(400 MHz, DMSO-d6): 8 8.75 (s, 1 H), 8.07 (s, 1 H), 7.67 (s, 1 H), 7.13 (dd, J = 8.8, 2.0 Hz, 1H), 7.02 (dd, J = 11.6, 8.4 Hz, 1 H), 6.80 (m, 1 H), 5.20 (s, 2 H), 4.25 (q, J = 6.8 Hz, 2 H),1.19 (t, J = 6.8 Hz, 3 H); MS (ESI) m/z: 318.2 [M+H(
  • 19
  • [ 1012880-02-2 ]
  • [ 858972-17-5 ]
  • [ 1012879-33-2 ]
YieldReaction ConditionsOperation in experiment
70% With aluminum oxide; potassium fluoride In N,N-dimethyl acetamide at 20℃; for 1h; A40 Example A40 KF/Al2O3 (40 wt %, 10 g, 69 mmol) was added to a solution of Example B2 (6 g, 30 mmol) and ethyl (3-amino-4-fluorophenyl)acetate (6 g, 30 mmol) in DMA (80 mL) and stirred at RT for 1 h. The mixture was filtered and the filtrate was concentrated under vacuum. The residue was poured into water, and the precipitate was collected by filtration, washed with Et2O, and dried in vacuo to give 3-(3-amino-4-fluorophenyl)-7-chloro-1-isopropyl-1,6-naphthyridin-2(1H)-one (7 g, 70% yield). 1H NMR (400 Hz, DMSO-d6): δ 8.71 (s, 1H), 8.00 (s, 1H), 7.76 (s, 1H), 7.11 (dd, J=9.2, 2.4 Hz, 1H), 7.05 (dd, J=11.6, 8.4 Hz, 1H), 6.76 (m, 1H), 5.18 (s, 2H), 5.15 (m, 1H), 1.52 (d, J=7.2 Hz, 1H); MS (ESI) m/z: 332.0 [M+H]+.
70% With 40% potassium fluoride/alumina In N,N-dimethyl acetamide at 20℃; for 1h; A40 Example A40: KF/Ab03 (40 wt %, 10 g, 69 mmol) was added to a solution ofExample B2 (6 g, 30 mmol) and ethyl (3-amino-4-fluorophenyl)acetate (6 g, 30 mmol) inDMA (80 mL) and stirred at RT for 1 h. The mixture was filtered and the filtrate wasconcentrated under vacuum. The residue was poured into water, and the precipitate wascollected by filtration, washed with Et20, and dried in vacuo to give 3-(3-amino-4-fluorophenyl)-7-chloro-1-isopropyl-1,6-naphthyridin-2(1H)-one (7 g, 70% yield). 1H NMR(400Hz, DMSO-d6): 8 8.71 (s, 1 H), 8.00 (s, 1 H), 7.76 (s, 1 H), 7.11 (dd, J = 9.2, 2.4 Hz, 1H), 7.05 (dd, J = 11.6, 8.4 Hz, 1 H), 6.76 (m, 1 H), 5.18 (s, 2 H), 5.15 (m, 1 H), 1.52 (d, J =7.2 Hz, 1 H); MS (ESI) m/z: 332.0 [M+Ht.
  • 20
  • [ 858972-17-5 ]
  • [ 1442471-26-2 ]
YieldReaction ConditionsOperation in experiment
With N-Bromosuccinimide In N,N-dimethyl-formamide at -25 - -20℃; for 3h; 1.3; 2.3; 3.3; 4.3; 5.3; 6.3; 7.3 3) Bromination reaction add 100 g of 3-amino-4-fluorophenyl ethyl acetate to another reaction flask, add 1000 mL of DMF, dissolve, cool to -25 to -20 ° C, and add 108 g of NBS in batches within 1 h , Reaction at -25 to -20 ° C for 3h. It was quenched by adding 3 L of water, extracted by adding 1 L of ethyl acetate, and washing the organic phase with 1 L of a saturated sodium carbonate aqueous solution, and concentrated to dryness.
  • 21
  • [ 192508-36-4 ]
  • [ 858972-17-5 ]
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