methyl 4-(difluoromethoxy)-3-(pyridin-2-ylethynyl)benzoate

Base Information

• Chemical Name: methyl 4-(difluoromethoxy)-3-(pyridin-2-ylethynyl)benzoate
• CAS No.: 1197357-97-3
• Molecular Formula: C₁₆H₁₁F₂NO₃
• Molecular Weight: 303.265
• Mol file: 1197357-97-3.mol

Synonyms:methyl 4-(difluoromethoxy)-3-(pyridin-2-ylethynyl)benzoate

Chemical Property of methyl 4-(difluoromethoxy)-3-(pyridin-2-ylethynyl)benzoate

Chemical Property:

Purity/Quality:

Safty Information:

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MSDS Files:

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Technology Process of methyl 4-(difluoromethoxy)-3-(pyridin-2-ylethynyl)benzoate

There total 2 articles about methyl 4-(difluoromethoxy)-3-(pyridin-2-ylethynyl)benzoate 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: 96.4%

2-ethynylpyridine (1945-84-2) + 4-difluoromethoxy-3-iodo-benzoic acid methyl ester (1131614-23-7) → methyl 4-(difluoromethoxy)-3-(pyridin-2-ylethynyl)benzoate (1197357-97-3)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; ammonium hydroxide; copper(l) iodide; In 1-methyl-pyrrolidin-2-one; at 40 ℃; for 6h; Inert atmosphere;

DOI:10.1021/acs.joc.9b02424

Reference yield:

methyl 3-iodo-4-hydroxybenzoate (15126-06-4) → methyl 4-(difluoromethoxy)-3-(pyridin-2-ylethynyl)benzoate (1197357-97-3)

Guidance literature:

Multi-step reaction with 2 steps

1: potassium carbonate / N,N-dimethyl-formamide / 0.25 h / 93 - 98 °C / Large scale

2: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; ammonium hydroxide; 1-methyl-pyrrolidin-2-one / 1 h / 35 - 40 °C / Inert atmosphere; Large scale

With 1-methyl-pyrrolidin-2-one; bis-triphenylphosphine-palladium(II) chloride; ammonium hydroxide; copper(l) iodide; potassium carbonate; In N,N-dimethyl-formamide; 2: |Sonogashira Cross-Coupling;

DOI:10.1021/op3002728

Reference yield: 99.1%

methyl 4-(difluoromethoxy)-3-(pyridin-2-ylethynyl)benzoate (1197357-97-3) → 4-(difluoromethoxy)-3-(pyridin-2-ylethynyl)benzoic acid (1197357-98-4)

Guidance literature:

methyl 4-(difluoromethoxy)-3-(pyridin-2-ylethynyl)benzoate; With sodium hydroxide; In methanol; water; at 35 - 40 ℃; for 1h; Large scale;

With acetic acid; In water; at 45 ℃; for 3h; Large scale;

DOI:10.1021/op3002728

upstream raw materials:

2-ethynylpyridine

4-difluoromethoxy-3-iodo-benzoic acid methyl ester

methyl 3-iodo-4-hydroxybenzoate

Downstream raw materials:

4-(difluoromethoxy)-3-(pyridin-2-ylethynyl)benzoic acid

(4-difluoromethoxy-3-pyridin-2-ylethynyl-phenyl)-(5,7-dihydro-pyrrolo[3,4-b]pyridin-6-yl)-methanone

1-{[4-(difluoromethoxy)-3-(pyridin-2-ylethynyl)phenyl]carbonyl}-4-pyridin-2-ylpiperazine

(4-(difluoromethoxy)-3-(pyridin-2-ylethynyl)phenyl)(5H-pyrrolo[3,4-b]pyridin-6(7H)-yl)methanone hydrochloride salt