Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 6872-06-6, name is 2-Methylindoline, A new synthetic method of this compound is introduced below., Computed Properties of C9H11N
Example 1Synthesis of 5-((2,3-dihydrobenzo[b][1,4]dioxin-6-yl)sulfonyl)-2-methyl-1-(methylsulfonyl)indolineReagents MW Mole Reagent/raw material (g/mole) Quantity moles ratio 2-methylindoline 161.20 1 g 7.5 mmol 1 eq. methanesulfonyl chloride 114.55 1.04 g 9.0 mmol 1.5 eq. 2-methyl-1-(methyl- 239.29 276 mg 1.3 mmol 1.2 eq. sulfonyl)indoline 2,3-dihydro- 375.93 250 mg 1.06 mmol 1.0 eq. benzo[b][1,4]dioxine- 6-sulfonyl chloride Aluminium chloride 133.3 170 mg 1.3 mmol 1.2 eq. Step I: 2-methylindoline was dissolved in 5 mL dry pyridine, and methanesulfonyl chloride was dropped in 2 portions under N2. The reaction was stirred for 2 hours at room temperature and an intense red color developed. When the reaction was complete as determined by HPLC (product Rt=8.51 min, st. material Rt=4.18 min) using the H2O-Acetonitrile (CAN) gradient given below with a Gemini-NS C18, 3 mum, 100 , 150¡Á4.6 mm column chromatography as well as by TLC (8/2 PE/EtOAC), the crude reaction was poured into 100 mL cold 0.5M HCl, and extracted twice with 50 mL CH2Cl2. The organic phase was evaporated, and the evaporation residue was purified by passing through a silica plug (100 g silica gel in large sinter glass). The product eluted in 7/3 PE/EtOAC, while all of the pink polar byproduct was retained on silica. The organic phase was dried on Na2SO4, and then evaporated and used for the next step without further purification (Product 100% pure, 455 mg, yield 30%).HPLC Purification Protocol Time (min) FlowH2O (%) ACN (%) 1 100 0 0.02 1 100 0 11.0 1 0 100 13.0 1 100 0 18.0 1 100 0 18.1 0.2 100 0
The synthetic route of 6872-06-6 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; Becker, Oren M.; Shitrit, Alina; Schutz, Nili; Ben-Zeev, Efrat; Yacovan, Avihai; Ozeri, Rachel; Kehat, Tzofit; Mirilashvili, Sima; Aizikovich, Alex; Sherman, Daniel; Behar, Vered; Kashtan, Osnat; US2012/108631; (2012); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem