156136-54-8

Upstream product

• 71293-62-4 5-trifluoromethyl-2-indolinone 
• 77-78-1 dimethyl sulfate 
• 56-23-5 tetrachloromethane 
• 61-70-1 N-methyl-2-indolinone 
• 59-48-3 2-oxoindole 
• 57946-63-1 4-amino-3-bromobenzotrifluoride 
• 175135-49-6 N-(2-bromo-4-(trifluoromethyl)phenyl)acetamide 

Downstream Products

• 156136-69-5 1-methyl-5-(trifluoromethyl)-2-indolinethione 
• 1027270-37-6 1-Methyl-2-thioxo-5-trifluoromethyl-2,3-dihydro-1H-indole-3-carboxylic acid phenylamide 

Relevant academic research and scientific papers

Regioselective electrophilic trifluoromethylation of indolines, oxindoles and indoles in superacid

Treatment of indolines and N-acylindoles with HF/SbF5/CCl 4 yields 6-trifluoro derivatives (indole numbering) whereas indoles and oxindoles give the 5-trifluoro derivatives in good yield.

Heterogeneous palladium-catalysed intramolecular C(sp3)[sbnd]H α-arylation for the green synthesis of oxindoles

Herein, we present our results on the development of a waste-minimized protocol for the synthesis of oxindoles using cyclopentyl methyl ether (CPME) as a safe and green reaction medium and palladium on carbon (Pd/C) as a reusable catalyst. This protocol is efficiently applied to a variety of substrates affording products with excellent yields, minimal metal contamination and minimum waste production. The catalyst was recovered and reused for four consecutive runs without any apparent loss of efficiency. Moreover, products were isolated by simple precipitation from heptane with no need for chromatographic separations, and both CPME and heptane were recovered. Waste-minimization is reflected by the low E-factor calculated for the presented protocol.

Tyrosine kinase inhibitors. 3. Structure-activity relationships for inhibition of protein tyrosine kinases by nuclear-substituted derivatives of 2,2'-dithiobis(1-methyl-N-phenyl-1H-indole-3-carboxamide)

A series of indole-substituted 2,2'-dithiobis(1-methyl-N-phenyl-1H- indole-3-carboxamides) were prepared and evaluated for their ability to inhibit the tyrosine kinase activity of both the epidermal growth factor receptor (EGFR) and the nonreceptor pp60(v-src) tyrosine kinase. The compounds were synthesized by conversion of appropriate 1-methyloxindoles to 1-methyl-2-indolinethiones with P2S5 followed by subsequent reaction with NaH and phenyl isocyanate and oxidative dimerization of the resulting 2,3- dihydro-N-phenyl-2-thioxo-1H-indole-3-carboxamides. The parent compound and many of the substituted analogues were moderately potent inhibitors of both kinase enzymes, but no clear relationships were seen between substitution on the indole ring and inhibitory activity. While 4-substituted compounds were generally inactive, 5-substituted derivatives with electron-withdrawing groups showed inhibitory activity. However, none of the substituted compounds showed significantly better activity than the unsubstituted parent compound. There was generally a good correlation between activity against the EGFR and pp60(v-src) kinases, but several compounds did show some specificity (>20- fold) of inhibition; 5-Cl and 5-Br derivatives preferentially inhibited pp60(v-src), while the 5-CF3 compound preferentially inhibited EGFR. Selected compounds from the series were found to inhibit the growth of Swiss 3T3 fibroblasts with IC50s in the range 2-25 μM, the most active being 4- substituted derivatives. The compounds inhibited bFGF-mediated protein tyrosine phosphorylation in intact cells more effectively than EGFR- or PDGF- mediated phosphorylation.

Oxindoles as sleep-inducers

Sleep inducers of the formula: STR1 wherein R is hydrogen or halo of atomic weight of from 18 to 36, R' is hydrogen, halo or CF3 and R° is hydrogen or lower alkyl. Preparation by cyclizing a 2-nitro-phenylacetic acid is also disclosed.