| Identification | Back Directory | [Name]
(3E)-2,3-Dihydro-3-(methoxyphenylmethylene)-2-oxo-1H-indole-6-carboxylic acid methyl ester | [CAS]
1168150-46-6 | [Synonyms]
(3E)-2
Nintedanib-017
BIBF1120 Intermediate4
Nintedanib Impurity 125
Nintedanib Intermediate 4
Nintedanib ethanesulfonate intermediates
oxo-1h-indole-6-carboxylic acid methyl ester
methyl (E)-3-(methoxy(phenyl)methylene)-2-oxoindoline-6-carboxylate
3-Dihydro-3-(methoxyphenylmethylene)-2-oxo-1H-indole-6-carboxylic acid methyl ester
(3E)-2,3-Dihydro-3-(methoxyphenylmethylene)-2-oxo-1H-indole-6-carboxylic acid methyl este
(3E)-2,3-Dihydro-3-(methoxyphenylmethylene)-2-oxo-1H-indole-6-carboxylic acid methyl ester
1H-Indole-6-carboxylic acid, 2,3-dihydro-3-(methoxyphenylmethylene)-2-oxo-, methyl ester, (3E)- | [EINECS(EC#)]
927-895-9 | [Molecular Formula]
C18H15NO4 | [MDL Number]
MFCD28139165 | [MOL File]
1168150-46-6.mol | [Molecular Weight]
309.32 |
| Chemical Properties | Back Directory | [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) | [form ]
Solid | [pka]
10.62±0.20(Predicted) | [color ]
Light Yellow |
| Hazard Information | Back Directory | [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 |
|
|