4-methyl-N-(3-(4-((trimethylsilyl)ethynyl)thiophen-3-yl)prop-2-yn-1-yl)benzenesulfonamide

Base Information

• Chemical Name: 4-methyl-N-(3-(4-((trimethylsilyl)ethynyl)thiophen-3-yl)prop-2-yn-1-yl)benzenesulfonamide
• CAS No.: 1610425-51-8
• Molecular Formula: C₁₉H₂₁NO₂S₂Si
• Molecular Weight: 387.599

Synonyms:4-methyl-N-(3-(4-((trimethylsilyl)ethynyl)thiophen-3-yl)prop-2-yn-1-yl)benzenesulfonamide

Chemical Property of 4-methyl-N-(3-(4-((trimethylsilyl)ethynyl)thiophen-3-yl)prop-2-yn-1-yl)benzenesulfonamide

Chemical Property:

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Technology Process of 4-methyl-N-(3-(4-((trimethylsilyl)ethynyl)thiophen-3-yl)prop-2-yn-1-yl)benzenesulfonamide

There total 2 articles about 4-methyl-N-(3-(4-((trimethylsilyl)ethynyl)thiophen-3-yl)prop-2-yn-1-yl)benzenesulfonamide 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: 75.0%

4-methyl-N-prop-2-ynylbenzenesulfonamide (55022-46-3) + 3-bromo-4-(trimethylsilyl)eth-1-yn-1-yl-thiophene (131390-83-5) → 4-methyl-N-(3-(4-((trimethylsilyl)ethynyl)thiophen-3-yl)prop-2-yn-1-yl)benzenesulfonamide (1610425-51-8)

Guidance literature:

4-methyl-N-prop-2-ynylbenzenesulfonamide; 3-bromo-4-(trimethylsilyl)eth-1-yn-1-yl-thiophene; With palladium diacetate; XPhos; In triethylamine; for 0.0833333h; Inert atmosphere;

With copper(l) iodide; In triethylamine; at 20 - 65 ℃; for 16h; Inert atmosphere;

DOI:10.1002/chem.201302967

Reference yield:

trimethylsilylacetylene (1066-54-2) → 4-methyl-N-(3-(4-((trimethylsilyl)ethynyl)thiophen-3-yl)prop-2-yn-1-yl)benzenesulfonamide (1610425-51-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide / triethylamine / 48 h / 60 °C

2.1: palladium diacetate; XPhos / triethylamine / 0.08 h / Inert atmosphere

2.2: 16 h / 20 - 65 °C / Inert atmosphere

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; palladium diacetate; XPhos; In triethylamine; 2.1: |Sonogashira Cross-Coupling;

DOI:10.1002/chem.201302967

Reference yield: 94.0%

4-methyl-N-(3-(4-((trimethylsilyl)ethynyl)thiophen-3-yl)prop-2-yn-1-yl)benzenesulfonamide (1610425-51-8) → N-(3-(4-ethynylthiophen-3-yl)prop-2-yn-1-yl)-4-methylbenzenesulfonamide (1583244-63-6)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 ℃; for 0.25h;

DOI:10.1002/chem.201302967

upstream raw materials:

4-methyl-N-prop-2-ynylbenzenesulfonamide

3-bromo-4-(trimethylsilyl)eth-1-yn-1-yl-thiophene

trimethylsilylacetylene

Downstream raw materials:

N-(3-(4-ethynylthiophen-3-yl)prop-2-yn-1-yl)-4-methylbenzenesulfonamide

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