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56341-41-4 Usage

Chemical Properties

Light Yellow Crystalline

Uses

5-Fluoro-2-oxindole (cas# 56341-41-4) is a compound useful in organic synthesis.

Application

5-Fluoro-2-oxindole is a ketone organic compound that can be used as an intermediate in the preparation of sunitinib. Sunitinib is a novel multi-targeted oral drug for the treatment of tumors.

Preparation

synthesis of 5-fluoro-2-oxindole: 4-fluoroaniline was used as the starting material, reacted with chloral hydrate and hydroxylamine hydrochloride to generate 4-fluoroisonitrosoacetanilide, and then cyclized under the action of concentrated sulfuric acid to form the compound 5-fluoroisatin was finally obtained by wolff-kishner-huang minlon reduction to obtain 5-fluoro-2-oxindole with a total yield of 66%.

Check Digit Verification of cas no

The CAS Registry Mumber 56341-41-4 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 5,6,3,4 and 1 respectively; the second part has 2 digits, 4 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 56341-41:
(7*5)+(6*6)+(5*3)+(4*4)+(3*1)+(2*4)+(1*1)=114
114 % 10 = 4
So 56341-41-4 is a valid CAS Registry Number.
InChI:InChI=1/C8H6FNO/c9-6-1-2-7-5(3-6)4-8(11)10-7/h1-3H,4H2,(H,10,11)

56341-41-4 Well-known Company Product Price

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  • (Code)Product description
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  • TCI America

  • (F0699)  5-Fluorooxindole  >98.0%(GC)

  • 56341-41-4

  • 1g

  • 590.00CNY

  • Detail
  • TCI America

  • (F0699)  5-Fluorooxindole  >98.0%(GC)

  • 56341-41-4

  • 5g

  • 1,690.00CNY

  • Detail
  • Alfa Aesar

  • (H32176)  5-Fluorooxindole, 97%   

  • 56341-41-4

  • 1g

  • 799.0CNY

  • Detail
  • Aldrich

  • (586579)  5-Fluoro-2-oxindole  97%

  • 56341-41-4

  • 586579-500MG

  • 1,105.65CNY

  • Detail

56341-41-4SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 5-Fluoro-2-oxindole

1.2 Other means of identification

Product number -
Other names Fluorooxindole

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:56341-41-4 SDS

56341-41-4Synthetic route

5-fluoro-1H-indole-2,3-dione
443-69-6

5-fluoro-1H-indole-2,3-dione

5-fluoroindol-2(3H)-one
56341-41-4

5-fluoroindol-2(3H)-one

Conditions
ConditionsYield
With hydrazine hydrate In water at 140℃; for 6h; Temperature; Wolff-Kishner-Huang Minlon Reduction;99.1%
With titanium tetrachloride; zinc In tetrahydrofuran at 20℃; for 0.1h; Inert atmosphere;87%
Stage #1: 5-fluoro-1H-indole-2,3-dione With potassium hydroxide; hydrazine In ethylene glycol at 80℃; for 3h;
Stage #2: With hydrogenchloride; water In ethylene glycol at 0 - 20℃; for 12h; pH=1 - 2;
81.9%
5-fluoro-2-oxo-2,3-dihydro-1H-indole-3-carboxylic acid methyl ester
389571-36-2

5-fluoro-2-oxo-2,3-dihydro-1H-indole-3-carboxylic acid methyl ester

5-fluoroindol-2(3H)-one
56341-41-4

5-fluoroindol-2(3H)-one

Conditions
ConditionsYield
With hydrogenchloride In methanol; water for 2h; Reagent/catalyst; Temperature; Inert atmosphere; Reflux;92.1%
Stage #1: 5-fluoro-2-oxo-2,3-dihydro-1H-indole-3-carboxylic acid methyl ester With hydrogenchloride In methanol; water at 80℃; for 5h;
Stage #2: With potassium hydroxide In methanol; water at 40℃; for 0.5h;
chloroacetyl chloride
79-04-9

chloroacetyl chloride

4-fluoroaniline
371-40-4

4-fluoroaniline

5-fluoroindol-2(3H)-one
56341-41-4

5-fluoroindol-2(3H)-one

Conditions
ConditionsYield
With montmorillonite KSF at 20℃; for 1.08333h; Stolle synthesis; Sonication; Neat (no solvent);88%
methyl 2-(5-fluoro-2-nitrophenyl)acetate
29640-99-1

methyl 2-(5-fluoro-2-nitrophenyl)acetate

5-fluoroindol-2(3H)-one
56341-41-4

5-fluoroindol-2(3H)-one

Conditions
ConditionsYield
With iron In acetic acid at 100℃; for 1h;87%
1,3-dihydro-1-hydroxyindole-2-one
18108-55-9

1,3-dihydro-1-hydroxyindole-2-one

5-fluoroindol-2(3H)-one
56341-41-4

5-fluoroindol-2(3H)-one

Conditions
ConditionsYield
With diethylamino-sulfur trifluoride In dichloromethane at 0℃; for 0.0833333h;81%
5-fluoro-3-hydrazonoindolin-2-one
283584-52-1

5-fluoro-3-hydrazonoindolin-2-one

5-fluoroindol-2(3H)-one
56341-41-4

5-fluoroindol-2(3H)-one

Conditions
ConditionsYield
With sodium ethanolate In ethanol for 5h; Reflux;80.4%
With potassium tert-butylate In ethanol for 2h; Reflux; Inert atmosphere;
With sodium ethanolate
4'-fluoroacetanilide
351-83-7

4'-fluoroacetanilide

ethyl iodoacetae
623-48-3

ethyl iodoacetae

5-fluoroindol-2(3H)-one
56341-41-4

5-fluoroindol-2(3H)-one

Conditions
ConditionsYield
With silver(I) acetate; palladium diacetate; trifluoroacetic acid at 120℃; for 24h; Sealed tube; Inert atmosphere; Schlenk technique;78%
(5-Fluoro-2-nitro-phenyl)-acetic Acid
29640-98-0

(5-Fluoro-2-nitro-phenyl)-acetic Acid

5-fluoroindol-2(3H)-one
56341-41-4

5-fluoroindol-2(3H)-one

Conditions
ConditionsYield
With ammonium formate on silica gel; zinc In carbon dioxide at 50℃; under 90009 Torr; Autoclave; liquid CO2;76%
(E)-5-fluoro-3-hydrazonoindolin-2-one

(E)-5-fluoro-3-hydrazonoindolin-2-one

5-fluoroindol-2(3H)-one
56341-41-4

5-fluoroindol-2(3H)-one

Conditions
ConditionsYield
With sodium ethanolate In ethanol for 6h; Reflux;73.6%
(2-amino-5-fluoro-phenyl)-acetic acid hydrazide
356068-89-8

(2-amino-5-fluoro-phenyl)-acetic acid hydrazide

5-fluoroindol-2(3H)-one
56341-41-4

5-fluoroindol-2(3H)-one

Conditions
ConditionsYield
In water73%
In water73%
With hydrogenchloride In water at 20℃; for 12h; pH=3;73%
(2-amino-5-fluoro-phenyl)-acetic acid hydrazide
356068-89-8

(2-amino-5-fluoro-phenyl)-acetic acid hydrazide

A

5-[5-fluoro-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-2,4-dimethyl-1H-pyrrole-3-carboxylic acid (2-diethylamino-ethyl)-amide

5-[5-fluoro-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-2,4-dimethyl-1H-pyrrole-3-carboxylic acid (2-diethylamino-ethyl)-amide

B

5-fluoroindol-2(3H)-one
56341-41-4

5-fluoroindol-2(3H)-one

Conditions
ConditionsYield
In waterA 73%
B n/a
In waterA 73%
B n/a
N'-(2-amino-5-fluorobenzylidene)-4-methylbenzenesulfonohydrazide

N'-(2-amino-5-fluorobenzylidene)-4-methylbenzenesulfonohydrazide

molybdenum hexacarbonyl
13939-06-5, 199620-15-0

molybdenum hexacarbonyl

5-fluoroindol-2(3H)-one
56341-41-4

5-fluoroindol-2(3H)-one

Conditions
ConditionsYield
With tetraethylammonium bromide; 1,8-diazabicyclo[5.4.0]undec-7-ene In 1,4-dioxane at 20 - 110℃; for 1h;55%
2-chloro-N-(4-fluorophenyl)acetamide
351-04-2

2-chloro-N-(4-fluorophenyl)acetamide

5-fluoroindol-2(3H)-one
56341-41-4

5-fluoroindol-2(3H)-one

Conditions
ConditionsYield
With aluminium trichloride at 220 - 225℃; for 0.5h;54%
With aluminum (III) chloride at 220℃; for 1h;
3,3-dibromo-5-fluoro-2-oxindole
113423-50-0

3,3-dibromo-5-fluoro-2-oxindole

5-fluoroindol-2(3H)-one
56341-41-4

5-fluoroindol-2(3H)-one

Conditions
ConditionsYield
With acetic acid; zinc Ambient temperature;
(2-tert-Butoxycarbonylamino-5-fluoro-phenyl)-acetic acid
138343-99-4

(2-tert-Butoxycarbonylamino-5-fluoro-phenyl)-acetic acid

5-fluoroindol-2(3H)-one
56341-41-4

5-fluoroindol-2(3H)-one

Conditions
ConditionsYield
With hydrogenchloride In ethanol for 0.25h; Heating; Yield given;
4-fluoroaniline
371-40-4

4-fluoroaniline

5-fluoroindol-2(3H)-one
56341-41-4

5-fluoroindol-2(3H)-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 54 percent / AlCl3 / 0.5 h / 220 - 225 °C
View Scheme
Multi-step reaction with 4 steps
1.1: hydrogenchloride; hydroxylamine hydrochloride; sodium sulfate / water / 60 - 70 °C
2.1: sulfuric acid / 80 - 90 °C
3.1: sulfuric acid; water
4.1: hydrazine hydrate / ethanol / Reflux
4.2: Reflux
View Scheme
Multi-step reaction with 2 steps
1: potassium carbonate / dichloromethane / 20 °C
2: aluminum (III) chloride / 1 h / 220 °C
View Scheme
2,4-Difluoronitrobenzene
446-35-5

2,4-Difluoronitrobenzene

5-fluoroindol-2(3H)-one
56341-41-4

5-fluoroindol-2(3H)-one

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 1) NaH / 1) DMSO, 100 deg C, 40 min, 2a) RT, 30 min, 2b) 100 deg C, 1 h
2: 56 percent / LiCl / dimethylsulfoxide; H2O / 3 h / 100 °C
3: 87 percent / Fe powder / acetic acid / 1 h / 100 °C
View Scheme
Multi-step reaction with 3 steps
1: sodium methylate / N,N-dimethyl acetamide / 10 °C / Inert atmosphere
2: palladium 10% on activated carbon; hydrogen / ethyl acetate; water / 20 °C
3: hydrogenchloride / water; methanol / 2 h / Inert atmosphere; Reflux
View Scheme
dimethyl 2-(5-fluoro-2-nitrophenyl)malonate
147124-34-3

dimethyl 2-(5-fluoro-2-nitrophenyl)malonate

5-fluoroindol-2(3H)-one
56341-41-4

5-fluoroindol-2(3H)-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 56 percent / LiCl / dimethylsulfoxide; H2O / 3 h / 100 °C
2: 87 percent / Fe powder / acetic acid / 1 h / 100 °C
View Scheme
4-fluor-2-methylaniline
452-71-1

4-fluor-2-methylaniline

5-fluoroindol-2(3H)-one
56341-41-4

5-fluoroindol-2(3H)-one

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: tetrahydrofuran / Heating
2: 1) s-BuLi / 1) THF, cyclohexane, -40 to -20 deg C, 2) -40 deg C, 1 min
3: 10percent HCl / ethanol / 0.25 h / Heating
View Scheme
tert-butyl (4-fluoro-2-methylphenyl)carbamate
129822-40-8

tert-butyl (4-fluoro-2-methylphenyl)carbamate

5-fluoroindol-2(3H)-one
56341-41-4

5-fluoroindol-2(3H)-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1) s-BuLi / 1) THF, cyclohexane, -40 to -20 deg C, 2) -40 deg C, 1 min
2: 10percent HCl / ethanol / 0.25 h / Heating
View Scheme
5-fluoro-1H-indole
399-52-0

5-fluoro-1H-indole

5-fluoroindol-2(3H)-one
56341-41-4

5-fluoroindol-2(3H)-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 48 percent / pyridinium bromide perbromide / 2-methyl-propan-2-ol / 20 h / 25 °C
2: Zn, AcOH / Ambient temperature
View Scheme
glacial acid

glacial acid

(5-Fluoro-2-nitro-phenyl)-acetic Acid
29640-98-0

(5-Fluoro-2-nitro-phenyl)-acetic Acid

5-fluoroindol-2(3H)-one
56341-41-4

5-fluoroindol-2(3H)-one

5-fluoro-3-methylthiooxindole

5-fluoro-3-methylthiooxindole

tert-butylhypochlorite
507-40-4

tert-butylhypochlorite

methylthioacetic acid ethyl ester
4455-13-4

methylthioacetic acid ethyl ester

4-fluoroaniline
371-40-4

4-fluoroaniline

5-fluoroindol-2(3H)-one
56341-41-4

5-fluoroindol-2(3H)-one

Conditions
ConditionsYield
With hydrogenchloride; triethylamine In diethyl ether; ethanol; dichloromethane; water
5-fluoro-3-methylthio-2-oxindole

5-fluoro-3-methylthio-2-oxindole

tert-butylhypochlorite
507-40-4

tert-butylhypochlorite

methylthioacetic acid ethyl ester
4455-13-4

methylthioacetic acid ethyl ester

4-fluoroaniline
371-40-4

4-fluoroaniline

5-fluoroindol-2(3H)-one
56341-41-4

5-fluoroindol-2(3H)-one

Conditions
ConditionsYield
With hydrogenchloride; triethylamine In diethyl ether; ethanol; dichloromethane; water
C8H5FN2O
1261152-93-5

C8H5FN2O

5-fluoroindol-2(3H)-one
56341-41-4

5-fluoroindol-2(3H)-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: sulfuric acid; water
2.1: hydrazine hydrate / ethanol / Reflux
2.2: Reflux
View Scheme
N-(4-fluorophenyl)-2-(hydroxyimino) acetamide
351-09-7

N-(4-fluorophenyl)-2-(hydroxyimino) acetamide

5-fluoroindol-2(3H)-one
56341-41-4

5-fluoroindol-2(3H)-one

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: sulfuric acid / 80 - 90 °C
2.1: sulfuric acid; water
3.1: hydrazine hydrate / ethanol / Reflux
3.2: Reflux
View Scheme
Multi-step reaction with 3 steps
1: sulfuric acid / 1 h / 50 - 70 °C
2: hydrazine hydrate / ethanol / 0.5 h / Inert atmosphere; Reflux
3: potassium tert-butylate / ethanol / 2 h / Reflux; Inert atmosphere
View Scheme
Multi-step reaction with 2 steps
1: sulfuric acid / 0.17 h / Inert atmosphere
2: titanium tetrachloride; zinc / tetrahydrofuran / 0.08 h / 20 °C / Inert atmosphere
View Scheme
Multi-step reaction with 2 steps
1: sulfuric acid / water / 50 - 75 °C
2: hydrazine hydrate / water / 6 h / 140 °C
View Scheme
Multi-step reaction with 2 steps
1: sulfuric acid / 2 h / 60 - 90 °C
2: hydrazine hydrate / water; ethanol / 10 h / 100 °C
View Scheme
5-fluoroindol-2(3H)-one
56341-41-4

5-fluoroindol-2(3H)-one

3-bromoazulene-1-carbaldehyde
42081-15-2

3-bromoazulene-1-carbaldehyde

(3E)-3-(((4Z,6Z,8E)-1-bromoazulen-3-yl)methylene)-5-fluoroindolin-2-one
1022916-57-9

(3E)-3-(((4Z,6Z,8E)-1-bromoazulen-3-yl)methylene)-5-fluoroindolin-2-one

Conditions
ConditionsYield
With piperidine In ethanol for 2h; Heating / reflux;100%
5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxylic acid
253870-02-9

5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxylic acid

5-fluoroindol-2(3H)-one
56341-41-4

5-fluoroindol-2(3H)-one

5-((5-fluoro-2-oxo-1,2-dihydro-3H-indol-3-ylidene)methyl)-2,4-dimethyl-1H-pyrrole-3-carboxylic acid
452105-33-8

5-((5-fluoro-2-oxo-1,2-dihydro-3H-indol-3-ylidene)methyl)-2,4-dimethyl-1H-pyrrole-3-carboxylic acid

Conditions
ConditionsYield
With pyrrolidine In ethanol for 3h; Reflux;98%
With pyrrolidine In ethanol for 3h; Reflux;98.2%
With piperidine In ethanol Inert atmosphere;90%
5-fluoroindol-2(3H)-one
56341-41-4

5-fluoroindol-2(3H)-one

formic acid ethyl ester
109-94-4

formic acid ethyl ester

5-fluoro-3-formyl-1H-indole-2-one

5-fluoro-3-formyl-1H-indole-2-one

Conditions
ConditionsYield
With sodium methylate In methanol Reflux;98%
5-fluoroindol-2(3H)-one
56341-41-4

5-fluoroindol-2(3H)-one

1,5-diphenyl-1,4-pentadiene-3-one
538-58-9

1,5-diphenyl-1,4-pentadiene-3-one

5'-fluoro-2,6-diphenylspiro[cyclohexane-1,3'-indoline]-2',4-dione
1374637-27-0

5'-fluoro-2,6-diphenylspiro[cyclohexane-1,3'-indoline]-2',4-dione

Conditions
ConditionsYield
With Boc-D-Phg-OH; 9-amino-9-deoxy-epiquinine In toluene at 40℃; for 72h; Air; optical yield given as %ee; enantioselective reaction;98%
5-fluoroindol-2(3H)-one
56341-41-4

5-fluoroindol-2(3H)-one

N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide
356068-86-5

N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide

sunitinib
557795-19-4

sunitinib

Conditions
ConditionsYield
With piperidine In toluene for 3h; Solvent; Reagent/catalyst; Knoevenagel Condensation; Reflux;97.3%
With piperidine In toluene for 3h; Reagent/catalyst; Solvent; Reflux;97.3%
With potassium hydroxide In N,N-dimethyl-formamide at 20℃; for 3.5h; Aldol Condensation; Darkness; Inert atmosphere;94%
5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxylic acid
253870-02-9

5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxylic acid

5-fluoroindol-2(3H)-one
56341-41-4

5-fluoroindol-2(3H)-one

5-((Z)-(5-fluoro-2-oxoindolin-3-ylidene)methyl)-2,4-dimethyl-1H-pyrrole-3-carboxylic acid
356068-93-4

5-((Z)-(5-fluoro-2-oxoindolin-3-ylidene)methyl)-2,4-dimethyl-1H-pyrrole-3-carboxylic acid

Conditions
ConditionsYield
Stage #1: 5-fluoroindol-2(3H)-one With ammonium sulfate; 1,1,1,3,3,3-hexamethyl-disilazane for 5h; Reflux;
Stage #2: 5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxylic acid With trimethylsilyl trifluoromethanesulfonate
97%
pyrrolidine In ethanol for 3h; Heating / reflux;96%
With pyrrolidine In ethanol for 3h; Heating / reflux;96%
3,5-dimethyl-4-nitro-1H-pyrrole-2-carbaldehyde
40236-20-2

3,5-dimethyl-4-nitro-1H-pyrrole-2-carbaldehyde

5-fluoroindol-2(3H)-one
56341-41-4

5-fluoroindol-2(3H)-one

(3Z)-[(3,5-dimethyl-4-nitro-1-hydropyrrol-2-yl)methylene]-5-fluoro-indol-2-one

(3Z)-[(3,5-dimethyl-4-nitro-1-hydropyrrol-2-yl)methylene]-5-fluoro-indol-2-one

Conditions
ConditionsYield
With pyrrolidine In ethanol Reflux;96%
With pyrrolidine In ethanol Reflux;96%
With pyrrolidine In ethanol Reflux;96%
With piperidine In ethanol Knoevenagel condensation; Heating;87%
With pyrrolidine In ethanol Reflux;
5-fluoroindol-2(3H)-one
56341-41-4

5-fluoroindol-2(3H)-one

3-iodo-1H-indazole-6-carbaldehyde
944904-42-1

3-iodo-1H-indazole-6-carbaldehyde

(E)-5-fluoro-3-((3-iodo-1H-indazol-6-yl)methylene)indolin-2-one

(E)-5-fluoro-3-((3-iodo-1H-indazol-6-yl)methylene)indolin-2-one

Conditions
ConditionsYield
With piperidine In methanol at 60℃; for 3h;96%
5-fluoroindol-2(3H)-one
56341-41-4

5-fluoroindol-2(3H)-one

5-[13C]formyl-2,4-dimethyl-1H-pyrrole-3-carboxylic acid
1194048-25-3

5-[13C]formyl-2,4-dimethyl-1H-pyrrole-3-carboxylic acid

5-((5-fluoro-2-oxo-1,2-dihydro-3H-indol-3-ylidene)-[13C]methyl)-2,4-dimethyl-1H-pyrrole-3-carboxylic acid

5-((5-fluoro-2-oxo-1,2-dihydro-3H-indol-3-ylidene)-[13C]methyl)-2,4-dimethyl-1H-pyrrole-3-carboxylic acid

Conditions
ConditionsYield
With pyrrolidine In ethanol for 3h; Reflux;95%
5-fluoroindol-2(3H)-one
56341-41-4

5-fluoroindol-2(3H)-one

malononitrile
109-77-3

malononitrile

2-(5-fluoro-2-oxoindolin-3-ylidene)malononitrile
116719-42-7

2-(5-fluoro-2-oxoindolin-3-ylidene)malononitrile

Conditions
ConditionsYield
With iron(III) chloride hexahydrate; oxygen In N,N-dimethyl-formamide at 50℃; for 4h; Green chemistry;95%
5-fluoroindol-2(3H)-one
56341-41-4

5-fluoroindol-2(3H)-one

methyl 2-oxobutanoate
3952-66-7

methyl 2-oxobutanoate

C13H14FNO4

C13H14FNO4

Conditions
ConditionsYield
With piperidine In methanol at 0 - 20℃; for 24h;93%
6-fluoro-1H-indole-3-carbaldehyde
2795-41-7

6-fluoro-1H-indole-3-carbaldehyde

5-fluoroindol-2(3H)-one
56341-41-4

5-fluoroindol-2(3H)-one

(Z)-5-fluoro-3-((5-fluoro-1H-indol-3-yl)methylene)indolin-2-one
1350703-09-1

(Z)-5-fluoro-3-((5-fluoro-1H-indol-3-yl)methylene)indolin-2-one

Conditions
ConditionsYield
With piperidine In methanol for 5h; Reflux;92%
5-fluoroindol-2(3H)-one
56341-41-4

5-fluoroindol-2(3H)-one

2,6-dimethyl-1-chlorobenzene
6781-98-2

2,6-dimethyl-1-chlorobenzene

C16H14FNO
1426306-74-2

C16H14FNO

Conditions
ConditionsYield
With C31H43Cl2N4Pd; potassium tert-butylate In toluene at 100℃; for 12h; Inert atmosphere; Schlenk technique;92%
5-fluoroindol-2(3H)-one
56341-41-4

5-fluoroindol-2(3H)-one

2-bromo-4-methoxybenzaldehyde
43192-31-0

2-bromo-4-methoxybenzaldehyde

3-(2-bromo-4-methoxybenzylidene)-5-fluoro-1,3-dihydroindol-2-one

3-(2-bromo-4-methoxybenzylidene)-5-fluoro-1,3-dihydroindol-2-one

Conditions
ConditionsYield
With piperidine In ethanol for 1.5h; Reflux;92%
5-fluoroindol-2(3H)-one
56341-41-4

5-fluoroindol-2(3H)-one

5-fluoro-1H-indole
399-52-0

5-fluoro-1H-indole

Conditions
ConditionsYield
With bis(trimethylsilyl)amide yttrium(III); 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane In toluene at 120℃; for 36h; Inert atmosphere;92%
With bis(trimethylsilyl)amide yttrium(III); 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane In toluene at 120℃; for 36h; Schlenk technique; Sealed tube; Inert atmosphere;86%
5-fluoroindol-2(3H)-one
56341-41-4

5-fluoroindol-2(3H)-one

C18H22N4O4

C18H22N4O4

C34H30F2N6O4

C34H30F2N6O4

Conditions
ConditionsYield
Stage #1: C18H22N4O4 With triethylamine In chloroform at 0℃; for 0.166667h;
Stage #2: 5-fluoroindol-2(3H)-one In chloroform at 65℃; for 8h; Solvent; Temperature;
92%
5-fluoroindol-2(3H)-one
56341-41-4

5-fluoroindol-2(3H)-one

acetic anhydride
108-24-7

acetic anhydride

1,3-diacetyl-5-fluoro-1H-indol-2-yl acetate
1268630-22-3

1,3-diacetyl-5-fluoro-1H-indol-2-yl acetate

Conditions
ConditionsYield
With dmap at 150℃; for 2h;91%
5-fluoroindol-2(3H)-one
56341-41-4

5-fluoroindol-2(3H)-one

3-(4-methoxyphenyl)propynal
90696-21-2

3-(4-methoxyphenyl)propynal

A

C18H12FNO2

C18H12FNO2

C28H22FNO5

C28H22FNO5

Conditions
ConditionsYield
With potassium tert-butylate; 1,3-bis(mesityl)imidazolium chloride In tetrahydrofuran at 20 - 65℃; for 2h; Molecular sieve; Inert atmosphere; optical yield given as %de; diastereoselective reaction;A 5%
B 91%
5-fluoroindol-2(3H)-one
56341-41-4

5-fluoroindol-2(3H)-one

4-chloromethoxybenzene
623-12-1

4-chloromethoxybenzene

C15H12FNO2
1426306-75-3

C15H12FNO2

Conditions
ConditionsYield
With C31H43Cl2N4Pd; potassium tert-butylate In toluene at 100℃; for 12h; Inert atmosphere; Schlenk technique;91%
2-methylquinoline
91-63-4

2-methylquinoline

5-fluoroindol-2(3H)-one
56341-41-4

5-fluoroindol-2(3H)-one

5-fluoro-3-hydroxy-3-(quinolin-2-ylmethyl)indolin-2-one

5-fluoro-3-hydroxy-3-(quinolin-2-ylmethyl)indolin-2-one

Conditions
ConditionsYield
With iron(II) acetate In N,N-dimethyl-formamide at 80℃; for 5h; Green chemistry;91%
5-fluoroindol-2(3H)-one
56341-41-4

5-fluoroindol-2(3H)-one

5-fluoroindoline-2-thione
73425-13-5

5-fluoroindoline-2-thione

Conditions
ConditionsYield
With tetraphosphorus decasulfide; sodium hydrogencarbonate In tetrahydrofuran at 20℃; for 4h;90%
With phosphorous (V) sulfide; sodium hydrogencarbonate In tetrahydrofuran for 3h; Ambient temperature;84%
Stage #1: 5-fluoroindol-2(3H)-one With tetraphosphorus decasulfide In tetrahydrofuran at 20℃; for 1h;
Stage #2: With sodium hydrogencarbonate In tetrahydrofuran at 120℃; for 1h;
75%
Stage #1: 5-fluoroindol-2(3H)-one With sodium hydrogencarbonate In tetrahydrofuran at 20℃; for 0.166667h;
Stage #2: With tetraphosphorus decasulfide In tetrahydrofuran at 20℃;
Stage #1: 5-fluoroindol-2(3H)-one With sodium hydrogencarbonate In tetrahydrofuran at 20℃; for 0.166667h;
Stage #2: With tetraphosphorus decasulfide In tetrahydrofuran at 20℃;
5-fluoroindol-2(3H)-one
56341-41-4

5-fluoroindol-2(3H)-one

(R)-5-(2-hydroxy-3-morpholin-4-yl-propyl)-3-methyl-4-oxo-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridine-2-carbaldehyde
1130138-32-7

(R)-5-(2-hydroxy-3-morpholin-4-yl-propyl)-3-methyl-4-oxo-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridine-2-carbaldehyde

(R,Z)-2-(5-fluoro-2-oxo-1,2-dihydro-indol-3-ylidenemethyl)-5-(2-hydroxy-3-morpholin-4-ylpropyl)-3-methyl-1,5,6,7-tetrahydro-pyrrolo[3,2-c]pyridin-4-one
1130137-76-6

(R,Z)-2-(5-fluoro-2-oxo-1,2-dihydro-indol-3-ylidenemethyl)-5-(2-hydroxy-3-morpholin-4-ylpropyl)-3-methyl-1,5,6,7-tetrahydro-pyrrolo[3,2-c]pyridin-4-one

Conditions
ConditionsYield
With piperidine In ethanol at 20 - 80℃; Darkness;90%
With piperidine In ethanol at 20 - 80℃; for 2h; Darkness;90%
With piperidine In ethanol at 20℃;
1-methyl-2-formyl-1H-benzimidazole
3012-80-4

1-methyl-2-formyl-1H-benzimidazole

5-fluoroindol-2(3H)-one
56341-41-4

5-fluoroindol-2(3H)-one

(E)-5-fluoro-3-((1-methyl-1H-benzo[d]imidazol-2-yl)methylene)indolin-2-one

(E)-5-fluoro-3-((1-methyl-1H-benzo[d]imidazol-2-yl)methylene)indolin-2-one

Conditions
ConditionsYield
With piperidine In ethanol Knoevenagel Condensation; Reflux; stereoselective reaction;90%
5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxylic acid
253870-02-9

5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxylic acid

5-fluoroindol-2(3H)-one
56341-41-4

5-fluoroindol-2(3H)-one

C14H21NO5

C14H21NO5

C30H32FN3O7

C30H32FN3O7

Conditions
ConditionsYield
Stage #1: 5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxylic acid With 1,1'-carbonyldiimidazole In tetrahydrofuran at 35℃; for 3h;
Stage #2: 5-fluoroindol-2(3H)-one; C14H21NO5 With triethylamine In tetrahydrofuran; acetonitrile at 60℃; for 24h;
90%
5-fluoroindol-2(3H)-one
56341-41-4

5-fluoroindol-2(3H)-one

3-[3-(diethylamino)propyl]-4-oxo-4,5,6,7-tetrahydro-1H-indole-2-carbaldehyde
1239441-14-5

3-[3-(diethylamino)propyl]-4-oxo-4,5,6,7-tetrahydro-1H-indole-2-carbaldehyde

(Z)-3-({3-[3-(diethylamino)propyl]-4-oxo-4,5,6,7-tetrahydro-1H-indol-2-yl}methylene)-5-fluoroindolin-2-one

(Z)-3-({3-[3-(diethylamino)propyl]-4-oxo-4,5,6,7-tetrahydro-1H-indol-2-yl}methylene)-5-fluoroindolin-2-one

Conditions
ConditionsYield
With piperidine In ethanol for 12h; Reflux;90%
5-fluoroindol-2(3H)-one
56341-41-4

5-fluoroindol-2(3H)-one

4-(4-formylphenoxy)-3-(trifluoromethyl)benzonitrile

4-(4-formylphenoxy)-3-(trifluoromethyl)benzonitrile

4-(4-((5-fluoro-2-oxoindolin-3-ylidene)methyl)-2-methoxyphenoxy)-3-(trifluoromethyl)benzonitrile

4-(4-((5-fluoro-2-oxoindolin-3-ylidene)methyl)-2-methoxyphenoxy)-3-(trifluoromethyl)benzonitrile

Conditions
ConditionsYield
With piperidine In ethanol at 60℃;90%
5-fluoroindol-2(3H)-one
56341-41-4

5-fluoroindol-2(3H)-one

ethyl 3-(2-formyl-4-oxo-4,5,6,7-tetrahydro-1H-indol-3-yl)propanoate
1235459-55-8

ethyl 3-(2-formyl-4-oxo-4,5,6,7-tetrahydro-1H-indol-3-yl)propanoate

(Z)-ethyl 3-{2-[(5-fluoro-2-oxoindolin-3-ylidene)methyl]-4-oxo-4,5,6,7-tetrahydro-1H-indol-3-yl}propanoate
1235458-09-9

(Z)-ethyl 3-{2-[(5-fluoro-2-oxoindolin-3-ylidene)methyl]-4-oxo-4,5,6,7-tetrahydro-1H-indol-3-yl}propanoate

Conditions
ConditionsYield
With piperidine In ethanol for 12h; Aldol condensation; Reflux;89%

56341-41-4Relevant articles and documents

Design, synthesis, and in vitro and in vivo anti-angiogenesis study of a novel vascular endothelial growth factor receptor-2 (VEGFR-2) inhibitor based on 1,2,3-triazole scaffold

Wang, De-pu,Liu, Kai-li,Li, Xin-yang,Lu, Guo-qing,Xue, Wen-han,Qian, Xin-hua,Mohamed O, Kamara,Meng, Fan-hao

, (2020/12/21)

In the past five years, our team had been committed to click chemistry research, exploring the biological activity of 1,2,3-triazole by synthesizing different target inhibitors. In this study, a series of novel indole-2-one derivatives based on 1,2,3-triazole scaffolds were synthesized for the first time, and their inhibitory activity on vascular endothelial growth factor receptor-2 (VEGFR-2) was tested. Most of the compounds had shown promising activity in the VEGFR-2 kinase assay and had low toxicity to human umbilical vein endothelial cells (HUVECs). The compound 13d (IC50 = 26.38 nM) had better kinase activity inhibition ability than sunitinib (IC50 = 83.20 nM) and was less toxic to HUVECs. Moreover, it had an excellent inhibitory effect on HT-29 and MKN-45 cells. On the one hand, by tube formation assay, transwell, and Western blot analysis, compound 13d could inhibit VEGFR-2 protein phosphorylate on HUVECs, thereby inhibiting HUVECs migration and tube formation. In vivo study, the zebrafish model with VEGFR-2 labeling also verified that compound 13d had more anti-angiogenesis ability than sunitinib. On the other hand, molecular docking and molecular dynamics (MD) simulation results showed that compound 13d could stably bind to the active site of VEGFR-2. Based on the above findings, compound 13d could be considered an effective anti-angiogenesis drug and has more development value than sunitinib.

DENDRIMER COMPOSITIONS AND METHODS FOR DRUG DELIVERY TO THE EYE

-

Paragraph 0214; 0215, (2021/06/11)

Dendrimer compositions and methods for the treatment of one or more inflammatory and/or angiogenic diseases and/or disorders of the eye include hydroxyl-terminated dendrimers complexed or conjugated with one or more active agents for the treatment or alleviation of one or more symptoms of the diseases of the eye, and/or for diagnosing the diseases and/or disorders of the eye. The dendrimers may include one or more ethylene diamine-core poly(amidoamine) (PAMAM) hydroxyl-terminated generation-4, 5, 6, 7, 8, 9, or 10 dendrimers. The active agents may be VEGFR tyrosine kinase inhibitors including sunitinib or analogues thereof. Preferably, the compositions are suitable for administration via a systemic route to target activated microglia/macrophages in retina/choroid.

Development of a novel conjugatable sunitinib analogue validated through in vitro and in vivo preclinical settings

El Mubarak, Mohamed A.,Leontari, Iliana,Efstathia, Giannopoulou,Vrettos, Eirinaios I.,Shaikh, Abdul kadar,Konstantinos, Siatis E.,Danika, Charikleia,Kalofonos, Haralabos P.,Tzakos, Andreas G.,Sivolapenko, Gregory B.

, p. 515 - 523 (2018/07/06)

Sunitinib is an oral FDA/EMEA approved multi-targeted tyrosine kinase inhibitor. It possesses anti-angiogenic and antitumor activity against a variety of advanced solid tumors. However, its chemical core does not allow a potential linkage to tumor-homing elements that could eventually enhance its potency. Therefore, a novel linkable sunitinib derivative, designated SB1, was rationally designed and synthesized. The pharmaceutical profile of SB1 was explored both in vitro and in vivo. Mass spectrometry and NMR spectroscopy were utilized for characterization, while MTT assays and LC-MS/MS validated protocols were used to explore its antiproliferative effect and stability, respectively. Cytotoxicity evaluation in three glioma cells showed that SB1 preserved the antiproliferative effect of sunitinib. SB1 was stable in vitro after 24 h incubation in mouse plasma, while both agents exhibited bioequivalent pharmacokinetic characteristics after i.v. administration in Balb/c mice. To evaluate the levels of SB1 in mouse plasma, a novel analytical method was developed and validated in accordance to the US FDA and the EU EMA guidelines. We formulated a novel linkable sunitinib analog exhibiting similar antiproliferative and apoptotic properties with native sunitinib in glioma cell lines. Both SB1 and native sunitinib showed identical in vitro stability in mouse plasma and pharmacokinetics after i.v. administration in Balb/c mice.

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