(S)-4-(4-((6-(2-(dimethylamino)ethyl)-6H-indolo[2,3-b]quinoxalin-9-yl)ethynyl)phenoxy)butane-1,2-diol

Base Information

• Chemical Name: (S)-4-(4-((6-(2-(dimethylamino)ethyl)-6H-indolo[2,3-b]quinoxalin-9-yl)ethynyl)phenoxy)butane-1,2-diol
• CAS No.: 1427039-97-1
• Molecular Formula: C₃₀H₃₀N₄O₃
• Molecular Weight: 494.593

Synonyms:(S)-4-(4-((6-(2-(dimethylamino)ethyl)-6H-indolo[2,3-b]quinoxalin-9-yl)ethynyl)phenoxy)butane-1,2-diol

Chemical Property of (S)-4-(4-((6-(2-(dimethylamino)ethyl)-6H-indolo[2,3-b]quinoxalin-9-yl)ethynyl)phenoxy)butane-1,2-diol

Chemical Property:

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Technology Process of (S)-4-(4-((6-(2-(dimethylamino)ethyl)-6H-indolo[2,3-b]quinoxalin-9-yl)ethynyl)phenoxy)butane-1,2-diol

There total 5 articles about (S)-4-(4-((6-(2-(dimethylamino)ethyl)-6H-indolo[2,3-b]quinoxalin-9-yl)ethynyl)phenoxy)butane-1,2-diol 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: 89.0%

(S)-4-(4-ethynylphenoxy)butane-1,2-diol (1427039-96-0) + 2-(9-bromo-6H-indolo[2,3-b]quinoxalin-6-yl)-N,N-dimethylethanamine (112228-63-4) → (S)-4-(4-((6-(2-(dimethylamino)ethyl)-6H-indolo[2,3-b]quinoxalin-9-yl)ethynyl)phenoxy)butane-1,2-diol (1427039-97-1)

Guidance literature:

2-(9-bromo-6H-indolo[2,3-b]quinoxalin-6-yl)-N,N-dimethylethanamine; With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; triphenylphosphine; In N,N-dimethyl-formamide; for 0.5h; Inert atmosphere;

(S)-4-(4-ethynylphenoxy)butane-1,2-diol; In N,N-dimethyl-formamide; at 120 ℃; for 0.416667h; Inert atmosphere; Microwave irradiation;

DOI:10.1080/15257770.2013.765013

Reference yield:

(S)-4-(2-(4-iodophenoxy)ethyl)-2,2-dimethyl-1,3-dioxolane (1088780-69-1) → (S)-4-(4-((6-(2-(dimethylamino)ethyl)-6H-indolo[2,3-b]quinoxalin-9-yl)ethynyl)phenoxy)butane-1,2-diol (1427039-97-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: acetic acid / water

2.1: triethylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide / 24 h / Inert atmosphere

3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 0 °C

4.1: triethylamine; triphenylphosphine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide / N,N-dimethyl-formamide / 0.5 h / Inert atmosphere

4.2: 0.42 h / 120 °C / Inert atmosphere; Microwave irradiation

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; tetrabutyl ammonium fluoride; acetic acid; triethylamine; triphenylphosphine; In tetrahydrofuran; water; N,N-dimethyl-formamide; 2.1: |Sonogashira Cross-Coupling / 4.1: |Sonogashira Cross-Coupling / 4.2: |Sonogashira Cross-Coupling;

DOI:10.1080/15257770.2013.765013

Reference yield:

(S)-4-(4-((trimethylsilyl)ethynyl)phenoxy)butane-1,2-diol (1427039-95-9) → (S)-4-(4-((6-(2-(dimethylamino)ethyl)-6H-indolo[2,3-b]quinoxalin-9-yl)ethynyl)phenoxy)butane-1,2-diol (1427039-97-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 0 °C

2.1: triethylamine; triphenylphosphine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide / N,N-dimethyl-formamide / 0.5 h / Inert atmosphere

2.2: 0.42 h / 120 °C / Inert atmosphere; Microwave irradiation

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; tetrabutyl ammonium fluoride; triethylamine; triphenylphosphine; In tetrahydrofuran; N,N-dimethyl-formamide; 2.1: |Sonogashira Cross-Coupling / 2.2: |Sonogashira Cross-Coupling;

DOI:10.1080/15257770.2013.765013

upstream raw materials:

(S)-4-(4-((trimethylsilyl)ethynyl)phenoxy)butane-1,2-diol

(S)-4-(4-ethynylphenoxy)butane-1,2-diol

2-(9-bromo-6H-indolo[2,3-b]quinoxalin-6-yl)-N,N-dimethylethanamine

(S)-4-(2-(4-iodophenoxy)ethyl)-2,2-dimethyl-1,3-dioxolane

Downstream raw materials:

(S)-1-(bis(4-methoxyphenyl)(phenyl)methoxy)-4-(4-((6-(2-(dimethylamino)ethyl)-6H-indolo[2,3-b]quinoxalin-9-yl)ethynyl)phenoxy)butan-2-ol

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