6-cyclopropylmethoxy-5-(3,3-difluoro-azetidin-1-yl)-pyridine-2-carboxylic acid

Base Information

• Chemical Name: 6-cyclopropylmethoxy-5-(3,3-difluoro-azetidin-1-yl)-pyridine-2-carboxylic acid
• CAS No.: 1415898-88-2
• Molecular Formula: C₁₃H₁₄F₂N₂O₃
• Molecular Weight: 284.263

Synonyms:6-cyclopropylmethoxy-5-(3,3-difluoro-azetidin-1-yl)-pyridine-2-carboxylic acid

Chemical Property of 6-cyclopropylmethoxy-5-(3,3-difluoro-azetidin-1-yl)-pyridine-2-carboxylic acid

Chemical Property:

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Technology Process of 6-cyclopropylmethoxy-5-(3,3-difluoro-azetidin-1-yl)-pyridine-2-carboxylic acid

There total 1 articles about 6-cyclopropylmethoxy-5-(3,3-difluoro-azetidin-1-yl)-pyridine-2-carboxylic acid 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:

methyl 5-bromopicolinate (29682-15-3) → 6-cyclopropylmethoxy-5-(3,3-difluoro-azetidin-1-yl)-pyridine-2-carboxylic acid (1415898-88-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 20 h / 60 °C

1.2: 2 h / 0 - 95 °C

2.1: caesium carbonate; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl / tris-(dibenzylideneacetone)dipalladium⁽⁰⁾ / toluene / 110 °C / Inert atmosphere

3.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 2 h / 20 °C

3.2: 110 °C

With sodium hydride; caesium carbonate; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl; 3-chloro-benzenecarboperoxoic acid; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; In dichloromethane; N,N-dimethyl-formamide; toluene; mineral oil;

Reference yield: 66.0%

6-cyclopropylmethoxy-5-(3,3-difluoro-azetidin-1-yl)-pyridine-2-carboxylic acid (1415898-88-2) + 2-(5-phenyl-1,3,4-oxadiazol-2-yl)propan-2-amine (68176-04-5) → 6-(cyclopropylmethoxy)-5-(3,3-difluoroazetidin-1-yl)-N-(2-(5-phenyl-1,3,4-oxadiazol-2-yl)propan-2-yl)picolinamide

Guidance literature:

6-cyclopropylmethoxy-5-(3,3-difluoro-azetidin-1-yl)-pyridine-2-carboxylic acid; With N-ethyl-N,N-diisopropylamine; 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride; In dichloromethane; at 20 ℃; for 0.5h;

2-(5-phenyl-1,3,4-oxadiazol-2-yl)propan-2-amine; In dichloromethane; at 20 ℃; for 16h;

DOI:10.1021/acs.jmedchem.5b00283

Reference yield: 56.0%

6-cyclopropylmethoxy-5-(3,3-difluoro-azetidin-1-yl)-pyridine-2-carboxylic acid (1415898-88-2) + 1-[5-(4-fluorophenyl)-1,3,4-oxadiazol-2-yl]-2-methylpropan-2-amine hydrochloride → 6-(cyclopropylmethoxy)-5-(3,3-difluoroazetidin-1-yl)-N-[1-[5-(4-fluorophenyl)-1,3,4-oxadiazol-2-yl]-2-methylpropan-2-yl]pyridine-2-carboxamide

Guidance literature:

6-cyclopropylmethoxy-5-(3,3-difluoro-azetidin-1-yl)-pyridine-2-carboxylic acid; With N-ethyl-N,N-diisopropylamine; 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride; In dichloromethane; at 20 ℃; for 0.5h;

1-[5-(4-fluorophenyl)-1,3,4-oxadiazol-2-yl]-2-methylpropan-2-amine hydrochloride; In dichloromethane; at 20 ℃;

upstream raw materials:

methyl 5-bromopicolinate

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