Some common heterocyclic compound, 356068-93-4, name is (Z)-5-((5-Fluoro-2-oxoindolin-3-ylidene)methyl)-2,4-dimethyl-1H-pyrrole-3-carboxylic acid, molecular formula is C16H13FN2O3, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Formula: C16H13FN2O3
Example 6 Preparation of 3-{5-[5-fluoro-2-oxo-1 ,2-dihydro-indol-(3Z)-ylidenemethyl]- 2,4-dimethyl-1 H-pyrrole-3-carbonyl}amino-propionic acid methyl ester. 5-[5-fluoro-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-2,4-dimethyl-1H-pyrrole-3-carbox- ylic acid (300 mg, 1 mmol) and 8 ml of DMF were stirred at room temperature while 1-Ethyl-3-(3-dimethyllaminopropyl)carbodiimide hydrochloride (384 mg, 2 mmol), hydroxybenzotriazole (162 mg, 1.2 mmol), triethylamine (404 mg, 4 mmol) and beta-alanine methyl ester hydrochloride (168.6 mg, 1.2 mmol) were added. The mixture was stirred for 20 hours at room temperature. The mixture was diluted with 400 mL of brine. The solids were collected by vacuum filtration, washed with water and dried under vacuum to give 2-{5-[5-fluoro-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-2,4-dimethyl-1H-pyrrole-3-car- bonyljamino-propionic acid methyl ester (333 mg, 87% yield) as a yellow solid. 1H NMR (DMSO-d6)delta2.39 (s, 3H, pyrrole-CH3), 2.41 (s, 3H, pyrrole-CH3), 2.58 (d, J= 8.0 Hz, 2H, CH2CO), 3.50 (m, 2H, NCH2), 3.63 (s, 3H, COOCH3), 6.84 (dd, J= 4.0 and 8.0 Hz, 1H, Ar-H), 6.92 (td, J= 4.0 and 8.0 Hz, 1H, Ar-H), 7.70 (s, 1H, vinyl-H), 7.67 (t, J= 4.0Hz, 1H, CONH), 7.75 (dd, J= 4.0 and 8.0 Hz, 1H1 Ar-H), 10.88 (s, 1 H, indolinone-NH), 13.66 (s, 1H, pyrrole-NH). LC-MS (m/z) 386 (M+1).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 356068-93-4, its application will become more common.
Reference:
Patent; SHENZEN CHIPSCREEN BIOSCIENCE, LTD.; WO2009/14941; (2009); A1;,
Indoline – Wikipedia,
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