14192-26-8,Some common heterocyclic compound, 14192-26-8, name is Methyl 2-oxoindoline-6-carboxylate, molecular formula is C10H9NO3, 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.
a) 1,3,3-trimethyl-2-oxoindoline-6-carboxylic acid To a suspension of NaH (60 % on mineral oil, 12.6 g, 314 mmol) in dry THF (260 ml) was added methyl 2-oxoindoline-6-carboxylate (15 g, 78.5 mmol) portionwise during 30 minutes. After gas-evolution ceased Mel (44.5 g, 19.6 ml, 314 mmol) was added dropwise with a syringe- pump during 80 minutes while carefully keeping the temperature between 24 C and 28 C. Thereaction mixture was stuffed for 2 hours at room temperature and then quenched by adding water (5.65 ml, 314 mmol) and then 32 % aqueous NaOH solution (19.6 g, 14.5 ml, 157 mmol) very carefully. The resulting mixture was poured into 100 mL TBME, the layers were separated and the organic layer was extracted with water. The combined aqueous layers were acidified with 25 % aqueous HC1 solution (20m1). The resulting suspension was filtered. The aqueous layer wasback-extracted with dichloromethane, the combined organic layers were dried with sodium sulfate and concentrated in vacuo. The obtained solid was combined with the filtered solid to give the title compound as light red solid (17.7 g).MS ESI (m/z): 220.2 [(M+H)i.1H NMR (DMSO-d6, 300 MHz) oe = 12.98 (br. s, 1H), 7.69 (dd, J=1.0, 7.7 Hz, 1H), 7.55 – 7.41(m, 2H), 3.18 (s, 3H), 1.29 (s, 6H).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 2-oxoindoline-6-carboxylate, its application will become more common.
Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; BRUNNER, Daniela; HILPERT, Hans; KOLCZEWSKI, Sabine; LIMBERG, Anja; MALBERG, Jessica; PRINSSEN, Eric; RIEMER, Claus; SHANKAR, Bavani G.; STOLL, Theodor; WO2014/202493; (2014); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem