(3E)-2,3-Dihydro-3-(methoxyphenylmethylene)-2-oxo-1H-indole-6-carboxylic acid methyl ester Chemical Properties

Boiling point:

523.8±50.0 °C(Predicted)

Density 

1.273±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

DMSO (Slightly), Methanol (Slightly)

pka

10.62±0.20(Predicted)

form 

Solid

color 

Light Yellow

(3E)-2,3-Dihydro-3-(methoxyphenylmethylene)-2-oxo-1H-indole-6-carboxylic acid methyl ester Usage And Synthesis

Uses

(E)-Methyl 3-(Methoxy(phenyl)methylene)-2-oxoindoline-6-carboxylate is an intermediate of (E)-Intedanib [I666670]. It is also used as a reactant in the preparation of deuterated derivatives of Nintedanib (N478290), which is angiokinase inhibitor with antitumor activity.

Synthesis

1. Methyl (3E)-1-(2-chloroacetyl)-2,3-dihydro-3-(methoxyphenylmethylene)-2-oxo-1H-indole-6-carboxylate (390.0 g, 1.0109 mol) was suspended in methanol (1562 mL) and heated to reflux. 2. A solution of potassium hydroxide (23.35 g, 0.35 equiv) in methanol (196.8 mL) was added slowly and the reaction was stirred for 40 minutes at reflux. 3. After the reaction is complete, the reaction mixture is cooled to 5 °C and stirring is continued for 30 min to promote product precipitation. 4. The precipitated product was collected by filtration, washed with cold methanol and subsequently dried under vacuum to afford methyl (E)-3-(methoxy(phenyl)methylene)-2-oxo dihydroindole-6-carboxylate 292.2 g in 93.5% yield.

References

[1] Patent: WO2012/68441, 2012, A2. Location in patent: Page/Page column 12; 13
[2] Patent: CN104003925, 2016, B. Location in patent: Paragraph 0161; 0163; 0178; 0179

(3E)-2,3-Dihydro-3-(methoxyphenylmethylene)-2-oxo-1H-indole-6-carboxylic acid methyl ester(1168150-46-6)Related Product Information

• Methyl 2-oxoindole-6-carboxylate
• 1-Chloro-4-(trimethoxymethyl)benzene
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