Introduction of a new synthetic route about 356068-93-4

Electric Literature of 356068-93-4,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.

EXAMPLE 9: Preparation of (Z)-5-((5-fluoro-2-oxoindolin-3-ylidene)methyl)- TV- (7-(hydroxyl-amino)-7-oxoheptyl)-2,4-dimethyl-lH-pyrrole- 3-carboxamide (Compound 15) Step 9a. (Z)-Methyl 7-(5-((5-fluoro-2-oxoindolin-3-ylidene)methyl)-2,4-dimethyl- lH-pyrrole-3-carboxamido)heptanoate (Compound 110-15)To a stirred solution of compound 109 (220.0 mg, 0.73 mmol) in DMF (15 mL) at room temperature was added etaOBt (148.6 mg, 1.1 mmol), triethylamine(0.21 mL, 1.46 mmol), ECDI-etaC1 (210.2 mg, 1.1 mmol) and methyl 7- aminoheptanoate hydrochloride (157.1 mg, 0.8 mmol) successively. The mixture was stirred for 24 h at room temperature and was then diluted with water (20 mL), brine (20 mL) and saturated bicarbonate solution (20 mL). The peta of the mixture was adjusted to 11-12 with 10 N NaOH. The mixture was filtered and the solid was washed with water, dried to obtain a crude product 110-15 as a yellow solid (0.3 g, 93.2%). LCMS: 442 [M+lf; 1H NMR(DMSO-^6): delta 1.31 (m, 4H), 1.50 (m, 4H), 2.31 (t, J= 7.35 Hz, 2H), 2.40 ( s, 3H), 2.42 (s,3H), 3.19 (m, 2H), 3.59 (s, 3H), 6.87 (m, 2H), 7.71 (m,3H), 10.91 (s, IH), 13.67 (s, IH).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route (Z)-5-((5-Fluoro-2-oxoindolin-3-ylidene)methyl)-2,4-dimethyl-1H-pyrrole-3-carboxylic acid, its application will become more common.

Reference:
Patent; CURIS, INC.; WO2008/33743; (2008); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem