methyl-3-[2-(4-ethynylphenoxy)acetamido]-4-hydroxybenzoate

Base Information

• Chemical Name: methyl-3-[2-(4-ethynylphenoxy)acetamido]-4-hydroxybenzoate
• CAS No.: 1427079-33-1
• Molecular Formula: C₁₈H₁₅NO₅
• Molecular Weight: 325.321
• Mol file: 1427079-33-1.mol

Synonyms:methyl-3-[2-(4-ethynylphenoxy)acetamido]-4-hydroxybenzoate

Chemical Property of methyl-3-[2-(4-ethynylphenoxy)acetamido]-4-hydroxybenzoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl-3-[2-(4-ethynylphenoxy)acetamido]-4-hydroxybenzoate

There total 10 articles about methyl-3-[2-(4-ethynylphenoxy)acetamido]-4-hydroxybenzoate 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:

C21H23NO5Si → methyl-3-[2-(4-ethynylphenoxy)acetamido]-4-hydroxybenzoate (1427079-33-1)

Guidance literature:

With potassium carbonate; In tetrahydrofuran; methanol; at 20 ℃; for 3h;

DOI:10.1016/j.bmcl.2012.11.081

Reference yield:

4-iodophenoxyacetic acid (1878-94-0) → methyl-3-[2-(4-ethynylphenoxy)acetamido]-4-hydroxybenzoate (1427079-33-1)

Guidance literature:

Multi-step reaction with 3 steps

1: benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N,N-diethylaniline / N,N-dimethyl-formamide / 20 °C / Inert atmosphere; Schlenk technique

2: bis-triphenylphosphine-palladium(II) chloride; triphenylphosphine; copper(l) iodide / N,N-dimethyl-formamide / 0.08 h / 120 °C / Inert atmosphere; Microwave irradiation; Schlenk technique

3: potassium carbonate / tetrahydrofuran; methanol / 12 h / 20 °C / Inert atmosphere; Schlenk technique

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; potassium carbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; triphenylphosphine; N,N-diethylaniline; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;

DOI:10.1016/j.jorganchem.2013.04.007

Reference yield:

3-nitro-4-hydroxybenzoic acid (616-82-0) → methyl-3-[2-(4-ethynylphenoxy)acetamido]-4-hydroxybenzoate (1427079-33-1)

Guidance literature:

Multi-step reaction with 5 steps

1: sulfuric acid / 12 h / Inert atmosphere; Schlenk technique; Reflux

2: palladium 10% on activated carbon; hydrogen / methanol / Inert atmosphere; Schlenk technique

3: benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N,N-diethylaniline / N,N-dimethyl-formamide / 20 °C / Inert atmosphere; Schlenk technique

4: bis-triphenylphosphine-palladium(II) chloride; triphenylphosphine; copper(l) iodide / N,N-dimethyl-formamide / 0.08 h / 120 °C / Inert atmosphere; Microwave irradiation; Schlenk technique

5: potassium carbonate / tetrahydrofuran; methanol / 12 h / 20 °C / Inert atmosphere; Schlenk technique

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; sulfuric acid; palladium 10% on activated carbon; hydrogen; potassium carbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; triphenylphosphine; N,N-diethylaniline; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;

DOI:10.1016/j.jorganchem.2013.04.007

upstream raw materials:

C₁₆H₁₄BrNO₅

4-bromo-phenol

ethyl 2-(4-bromophenoxy)acetate

(4-bromophenoxy)acetic acid

Downstream raw materials:

C₁₈H₂₅B₁₀NO₅

Refernces

• 1、 Nakamura, Hiroyuki,Yasui, Yuka,Maruyama, Minako,Minegishi, Hidemitsu,Ban, Hyun Seung,Sato, Shinichi. "Development of hypoxia-inducible factor (HIF)-1α inhibitors: Effect of ortho-carborane substituents on HIF transcriptional activity under hypoxia". . p. 806 - 810. Retrieved 2013/02/25.