Synthesis method of near-infrared two-region fluorescent dye FD-1080

A synthesis method and technology of fluorescent dyes, applied in the direction of organic dyes, luminescent materials, chemical instruments and methods, etc., can solve the problems of high production cost and high price of FD-1080, and achieve the effect of increasing yield and simple treatment

Active Publication Date: 2022-07-26
西安康福诺生物科技有限公司
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Problems solved by technology

[0010] In order to solve the problem of high production cost and high price of FD-1080, the present invention provides a low-cost method for synthesizing FD-1080

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  • Synthesis method of near-infrared two-region fluorescent dye FD-1080
  • Synthesis method of near-infrared two-region fluorescent dye FD-1080
  • Synthesis method of near-infrared two-region fluorescent dye FD-1080

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Embodiment 1

[0040] 1. Add 10g (0.059mol) of benzo[cd]indol-2(1H)-one to a 500mL round-bottomed flask, then add 100mL of acetonitrile and stir until benzo[cd]indol-2(1H)-one All dissolved, then 10.83g (0.088mol) 4-dimethylaminopyridine was added, and finally 19.35g (0.088mol) di-tert-butyl dicarbonate was added to the round-bottomed flask in batches under stirring. A large number of bubbles were generated but there was no obvious heating phenomenon, and the bottle was a turbid liquid. After adding the material, the solid in the bottle was ultrasonicated for 2 minutes to make it evenly dispersed, and the reaction was stirred at room temperature for 2 hours. First, the acetonitrile was distilled off under reduced pressure, and then 0.5mol / L hydrochloric acid was added. The unreacted 4-dimethylaminopyridine was washed away, and finally the mixture was extracted twice with ethyl acetate. The organic phase was dried with anhydrous sodium sulfate and concentrated. After the concentration was comp...

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Abstract

The invention discloses a synthesis method of near-infrared two-zone fluorescent dye FD-1080, which comprises the following steps: by taking benzo [cd] indol-2 (1H)-ketone as a starting material, firstly introducing tert-butylcarbonyl (Boc) on amido to protect the amido, then introducing methyl by utilizing a Grignard reagent in a ring opening manner, and then completing Boc protecting group removal and intramolecular cyclization reaction in one step by using an ethyl acetate solution of hydrogen chloride to obtain the near-infrared two-zone fluorescent dye FD-1080. The synthesis method comprises the following steps of: firstly, introducing sulfonic acid through nucleophilic substitution, and finally reacting with N-[(3-(anilinomethylene)-2-chloro-1-cyclohexene-1-yl) methylene] aniline hydrochloride to synthesize FD-1080, the whole synthesis process is safe and pollution-free, a product with higher purity can be synthesized without column chromatography purification, and the synthesis method can be used for amplified production of FD-1080.

Description

technical field [0001] The invention belongs to the technical field of synthesizing fluorescent dyes, and particularly relates to a method for synthesizing near-infrared second-region fluorescent dyes. Background technique [0002] Fluorescence bioimaging uses fluorescent signals emitted by fluorescent probes to perform optical imaging of cells, tissues or organisms. Compared with imaging techniques such as nuclear magnetic resonance imaging, it has high safety, high temporal resolution, high spatial resolution, With the characteristics of no radiation, low cost and non-destructive testing, it has become a popular research direction in the field of biomedical imaging. Fluorescence imaging can be divided into three regions according to its emission wavelength: visible light region (400-700nm), near-infrared region (NIR-I, 700-900nm) and near-infrared region (NIR-II, 1000-1700nm). NIR-II can also be subdivided into three sub-windows of NIR-IIa' (1000-1300 nm), NIR-IIa (1300-1...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/56C09B23/10C09K11/06
CPCC07D209/56C09B23/107C09K11/06C09K2211/1007C09K2211/1029Y02P20/55
Inventor 杨原
Owner 西安康福诺生物科技有限公司
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