3-O-methyl-17α-{4-[(pyrrolidin-1-yl)-azo]phenylethynyl}estra-1,3,5(10)-trien-3,17β-diol

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Chemical Name:3-O-methyl-17α-{4-[(pyrrolidin-1-yl)-azo]phenylethynyl}estra-1,3,5(10)-trien-3,17β-diol
CAS No.:643764-59-4
Molecular Formula:C₃₁H₃₇N₃O₂
Molecular Weight:483.654
Hs Code.:

Synonyms:3-O-methyl-17α-{4-[(pyrrolidin-1-yl)-azo]phenylethynyl}estra-1,3,5(10)-trien-3,17β-diol

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Chemical Property of 3-O-methyl-17α-{4-[(pyrrolidin-1-yl)-azo]phenylethynyl}estra-1,3,5(10)-trien-3,17β-diol

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Technology Process of 3-O-methyl-17α-{4-[(pyrrolidin-1-yl)-azo]phenylethynyl}estra-1,3,5(10)-trien-3,17β-diol

There total 3 articles about 3-O-methyl-17α-{4-[(pyrrolidin-1-yl)-azo]phenylethynyl}estra-1,3,5(10)-trien-3,17β-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: 53.0%

: 1624-62-0
estrone 3-methyl ether

: 196599-46-9
1-[2-(4-ethynylphenyl)diazenyl]pyrrolidine

: 643764-59-4
3-O-methyl-17α-{4-[(pyrrolidin-1-yl)-azo]phenylethynyl}estra-1,3,5(10)-trien-3,17β-diol

Guidance literature:: 1-[2-(4-ethynylphenyl)diazenyl]pyrrolidine; With lithium diisopropyl amide; In tetrahydrofuran; n-heptane; ethylbenzene; at -78 ℃; for 1h;

estrone 3-methyl ether; In tetrahydrofuran; n-heptane; ethylbenzene; at 20 ℃; for 24h;
DOI:10.1515/znb-2003-0813

Reference yield:

: 106-40-1
4-bromo-aniline

: 643764-59-4
3-O-methyl-17α-{4-[(pyrrolidin-1-yl)-azo]phenylethynyl}estra-1,3,5(10)-trien-3,17β-diol

Guidance literature:: Multi-step reaction with 4 steps

1.1: NaNO₂; HCl

1.2: 64 percent / KOH

2.1: 91 percent / Et₃N; CuI / (PPh₃)2PdCl₂ / 48 h / 70 °C

3.1: 58 percent / KOH / methanol / 5 h

4.1: LDA / tetrahydrofuran; heptane; ethylbenzene / 1 h / -78 °C

4.2: 53 percent / tetrahydrofuran; heptane; ethylbenzene / 24 h / 20 °C

With hydrogenchloride; potassium hydroxide; copper(l) iodide; triethylamine; lithium diisopropyl amide; sodium nitrite; bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; methanol; n-heptane; ethylbenzene; 2.1: Sonogashira coupling;
DOI:10.1515/znb-2003-0813

Reference yield:

: 196599-76-5
1-(4-trimethylsilylethynylphenyl)-3,3-tetramethylenetriazene

: 643764-59-4
3-O-methyl-17α-{4-[(pyrrolidin-1-yl)-azo]phenylethynyl}estra-1,3,5(10)-trien-3,17β-diol

Guidance literature:: Multi-step reaction with 2 steps

1.1: 58 percent / KOH / methanol / 5 h

2.1: LDA / tetrahydrofuran; heptane; ethylbenzene / 1 h / -78 °C

2.2: 53 percent / tetrahydrofuran; heptane; ethylbenzene / 24 h / 20 °C

With potassium hydroxide; lithium diisopropyl amide; In tetrahydrofuran; methanol; n-heptane; ethylbenzene;
DOI:10.1515/znb-2003-0813