difluoro[5-[3-hexylthiophen-2-yl]-1-[[5-[3-hexylthiophen-2-yl]-3-(2-methoxyphenyl)-2H-isoindole-1-yl]methylene]-3-(2-methoxyphenyl)-1H-isoindolate-N₁,N₂]boron

Base Information

• Chemical Name: difluoro[5-[3-hexylthiophen-2-yl]-1-[[5-[3-hexylthiophen-2-yl]-3-(2-methoxyphenyl)-2H-isoindole-1-yl]methylene]-3-(2-methoxyphenyl)-1H-isoindolate-N₁,N₂]boron
• CAS No.: 1329997-38-7
• Molecular Formula: C₅₁H₅₁BF₂N₂O₂S₂
• Molecular Weight: 836.918

Synonyms:difluoro[5-[3-hexylthiophen-2-yl]-1-[[5-[3-hexylthiophen-2-yl]-3-(2-methoxyphenyl)-2H-isoindole-1-yl]methylene]-3-(2-methoxyphenyl)-1H-isoindolate-N₁,N₂]boron

Chemical Property of difluoro[5-[3-hexylthiophen-2-yl]-1-[[5-[3-hexylthiophen-2-yl]-3-(2-methoxyphenyl)-2H-isoindole-1-yl]methylene]-3-(2-methoxyphenyl)-1H-isoindolate-N₁,N₂]boron

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Technology Process of difluoro[5-[3-hexylthiophen-2-yl]-1-[[5-[3-hexylthiophen-2-yl]-3-(2-methoxyphenyl)-2H-isoindole-1-yl]methylene]-3-(2-methoxyphenyl)-1H-isoindolate-N₁,N₂]boron

There total 5 articles about difluoro[5-[3-hexylthiophen-2-yl]-1-[[5-[3-hexylthiophen-2-yl]-3-(2-methoxyphenyl)-2H-isoindole-1-yl]methylene]-3-(2-methoxyphenyl)-1H-isoindolate-N₁,N₂]boron which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 83.0%

difluoro[5-bromo-1-[[5-bromo-3-(2-methoxyphenyl)-2H-isoindole-l-yl]methylene]-3-(2-methoxyphenyl)-1H-isoindolate-N1,N2]boron (1329997-37-6) + 2-(3-hexylthiophen-2-yl)-5,5-dimethyl-1,3,2-dioxaborinane → difluoro[5-[3-hexylthiophen-2-yl]-1-[[5-[3-hexylthiophen-2-yl]-3-(2-methoxyphenyl)-2H-isoindole-1-yl]methylene]-3-(2-methoxyphenyl)-1H-isoindolate-N1,N2]boron (1329997-38-7)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate; In tetrahydrofuran; water; for 16h; Inert atmosphere; Reflux;

DOI:10.1021/ol201770g

Reference yield:

1-(4-bromo-2-(2-methoxybenzoyl)phenyl)ethanone (1329709-96-7) → difluoro[5-[3-hexylthiophen-2-yl]-1-[[5-[3-hexylthiophen-2-yl]-3-(2-methoxyphenyl)-2H-isoindole-1-yl]methylene]-3-(2-methoxyphenyl)-1H-isoindolate-N1,N2]boron (1329997-38-7)

Guidance literature:

Multi-step reaction with 3 steps

1: ammonium hydroxide / methanol; acetic acid / 120 h / 40 °C

2: boron trifluoride diethyl etherate; triethylamine / toluene / 12 h / 100 °C

3: tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate / tetrahydrofuran; water / 16 h / Inert atmosphere; Reflux

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; boron trifluoride diethyl etherate; potassium carbonate; ammonium hydroxide; triethylamine; In tetrahydrofuran; methanol; water; acetic acid; toluene; 3: Suzuki coupling;

DOI:10.1021/ol201770g

Reference yield:

5-bromo-1-((5-bromo-3-(2-methoxyphenyl)-2H-isoindol-1-yl)methylene)-3-(2-methoxyphenyl)-1H-isoindole (1329709-97-8) → difluoro[5-[3-hexylthiophen-2-yl]-1-[[5-[3-hexylthiophen-2-yl]-3-(2-methoxyphenyl)-2H-isoindole-1-yl]methylene]-3-(2-methoxyphenyl)-1H-isoindolate-N1,N2]boron (1329997-38-7)

Guidance literature:

Multi-step reaction with 2 steps

1: boron trifluoride diethyl etherate; triethylamine / toluene / 12 h / 100 °C

2: tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate / tetrahydrofuran; water / 16 h / Inert atmosphere; Reflux

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; boron trifluoride diethyl etherate; potassium carbonate; triethylamine; In tetrahydrofuran; water; toluene; 2: Suzuki coupling;

DOI:10.1021/ol201770g

upstream raw materials:

(Z)-N'-(1-(4-bromo-2-hydroxyphenyl)ethylidene)-2-methoxybenzohydrazide

1-(4-bromo-2-(2-methoxybenzoyl)phenyl)ethanone

5-bromo-1-((5-bromo-3-(2-methoxyphenyl)-2H-isoindol-1-yl)methylene)-3-(2-methoxyphenyl)-1H-isoindole

difluoro[5-bromo-1-[[5-bromo-3-(2-methoxyphenyl)-2H-isoindole-l-yl]methylene]-3-(2-methoxyphenyl)-1H-isoindolate-N¹,N²]boron

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