Extracurricular laboratory: Synthetic route of 171290-52-1

The synthetic route of 171290-52-1 has been constantly updated, and we look forward to future research findings.

171290-52-1, name is 3,5-Dimethoxyphenylacetylene, belongs to ethers-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Application In Synthesis of 3,5-Dimethoxyphenylacetylene

To a solution of 69 benzyl-3-(8-amino-1-bromoimidazo[1,5-a]pyrazin-3-yl)azetidine-1-carboxylate 2e (0.123 g, 0.31 mmol), 43 1-ethynyl-3,5-dimethoxybenzene (0.740 g, 3.10 mmol) and 44 triethylamine (0.310 g, 3.10 mmol) in 32 N,N-dimethylformamide (5 mL), under nitrogen protection, were added 45 cuprous iodide (12 mg, 0.06 mmol) and 46 1,1?-bis(diphenylphosphino)ferrocene-palladium(II) dichloride (22 mg, 0.03 mmol). The mixture was heat to 80 C. and stirred for 5 h. The mixture was cooled to room temperature, quenched with saturated ammonium chloride solution (10 mL) and extracted with dichloromethane (50 mL×3). The combined organic phase was washed with brine (20 mL×2), dried over anhydrous sodium sulfate and filtered. The residue was purified by preparative-TLC (19:1 dichloromethane/methanol) to provide 71 benzyl-3-(8-amino-1-((3,5-dimethoxyphenyl)ethynyl)imidazo [1,5-a]pyrazin-3-yl)azetidine-1-carboxylate2f (52.5 mg, 0.11 mmol, grey solid), yield: 35%.MS m/z (ESI): 484 [M+1].

The synthetic route of 171290-52-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GUANGZHOU INNOCARE PHARMA TECH CO., LTD.; KONG, Norman Xianglong; ZHOU, Chao; CHEN, Xiangyang; US2019/177333; (2019); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem