ChemicalBook CAS DataBase List 5-((Z)-(5-Fluoro-2-oxoindolin-3-ylidene)methyl)-2,4-dimethyl-1H-pyrrole-3-carboxylic acid

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

7synthesis methods

Product Name:5-((Z)-(5-Fluoro-2-oxoindolin-3-ylidene)methyl)-2,4-dimethyl-1H-pyrrole-3-carboxylic acid
CAS Number:356068-93-4
Molecular formula:C16H13FN2O3
Molecular Weight:300.28

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

253870-02-9

56341-41-4

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

356068-93-4

Ammonium sulfate ((NH4)2SO4, 0.09 g, 0.67 mmol) was added to hexamethyldisilazane (HMDS, 20 mL) as 2,4-dimethyl-5-formyl-1H-pyrrole-3-carboxylic acid (8, 1.0 g, 6.61 mmol) and 5-fluoroindol-2-one (14, 1.1 g, 3.77 mmol) at room temperature in a stirred mixture. Subsequently, the reaction mixture was heated to reflux and maintained at this temperature for at least 5 h. The reaction process was monitored by gas chromatography (GC). Upon completion of the reaction, 5-fluoroindol-2-one (14) and trimethylsilyl trifluoromethanesulfonate (TMSOTf, 0.29 g, 1.32 mmol) were added. Stirring of the mixture was continued until high performance liquid chromatography (HPLC) analysis showed that the reaction was complete. The reaction mixture was quenched with water (6 mL) and acetonitrile (MeCN, 30 mL), filtered and the filter cake was washed sequentially with acetonitrile (20 mL) and ethanol (EtOH, 5 mL). Finally, the product was dried under vacuum at 40 °C overnight to afford the target compound 5-((Z)-(5-fluoro-2-oxoindolidine-3-ylidene)methyl)-2,4-dimethyl-1H-pyrrole-3-carboxylic acid (15, 1.92 g, 97% yield) as a yellow to brown powder with an HPLC purity of about 82.1%.

253870-02-9 Synthesis

253870-02-9
383 suppliers
$6.00/1g

56341-41-4 Synthesis

56341-41-4
542 suppliers
$12.00/5g

356068-93-4
152 suppliers
$45.00/25mg

Yield: 97%

Reaction Conditions:

Stage #1:5-fluoroindol-2(3H)-one with ammonium sulfate;1,1,1,3,3,3-hexamethyl-disilazane for 5 h;Reflux;
Stage #2:5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxylic acid with trimethylsilyl trifluoromethanesulfonate

Steps:

17 Example 17 Synthesis of 15 Using TMSOTf in One-Pot
(NH₄)₂SO₄ (0.09 g, 0.67 mmol) was added into a stirred mixture of 8 (1.0 g, 6.61 mmol) in HMDS (20 mL, 20 P) at room temperature.
The reaction mixture was then heated to reflux and maintained at that temperature for no less than 5 hours.
Monitor the reaction by GC.
After the reaction is completed, 14 (1.1 g, 3.77 mmol) and TMSOTf (0.29 g, 1.32 mmol) were added.
Then the mixture was stirred, once the reaction was complete (as indicated by HPLC analysis) it was quenched with water (6 mL, 6 P.) and MeCN (30 mL).
The mixture was filtrated and the filtrate cake was washed with MeCN (20 mL) and EtOH (5 mL), then it was dried under vacuum at 40° C. overnight to give the goal product 15 (1.92 g, 97% yield) as a yellow to brown powder with about 82.1% HPLC purity.

References:

SCINOPHARM TAIWAN, LTD.;Henscheke, Julian P.;Chen, Yung-Fa US2013/190512, 2013, A1 Location in patent:Paragraph 0088

123-75-1 Synthesis