(S)-3-((5-(azetidin-2-ylmethoxy)pyridin-3-yl)ethynyl)-5-fluoro-N,N-dimethylaniline

Base Information

Chemical Name:(S)-3-((5-(azetidin-2-ylmethoxy)pyridin-3-yl)ethynyl)-5-fluoro-N,N-dimethylaniline
CAS No.:1434047-69-4
Molecular Formula:C₁₉H₂₀FN₃O
Molecular Weight:325.386
Hs Code.:

Synonyms:(S)-3-((5-(azetidin-2-ylmethoxy)pyridin-3-yl)ethynyl)-5-fluoro-N,N-dimethylaniline

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Chemical Property of (S)-3-((5-(azetidin-2-ylmethoxy)pyridin-3-yl)ethynyl)-5-fluoro-N,N-dimethylaniline

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Technology Process of (S)-3-((5-(azetidin-2-ylmethoxy)pyridin-3-yl)ethynyl)-5-fluoro-N,N-dimethylaniline

There total 5 articles about (S)-3-((5-(azetidin-2-ylmethoxy)pyridin-3-yl)ethynyl)-5-fluoro-N,N-dimethylaniline 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: 72.0%

: 1434047-83-2
(S)-tert-butyl 2-((5-((3-(dimethylamino)-5-fluorophenyl)ethynyl)pyridin-3-yloxy)methyl)azetidine-1-carboxylate

: 1434047-69-4
(S)-3-((5-(azetidin-2-ylmethoxy)pyridin-3-yl)ethynyl)-5-fluoro-N,N-dimethylaniline

Guidance literature:: (S)-tert-butyl 2-((5-((3-(dimethylamino)-5-fluorophenyl)ethynyl)pyridin-3-yloxy)methyl)azetidine-1-carboxylate; With trifluoroacetic acid; In dichloromethane; at 0 ℃; for 5h; Inert atmosphere;

With sodium hydroxide; In methanol; water; at 0 ℃; for 18h; pH=9 - 10;
DOI:10.1021/jm4008455

Reference yield: 72.0%

: 1434047-69-4
(S)-3-((5-(azetidin-2-ylmethoxy)pyridin-3-yl)ethynyl)-5-fluoro-N,N-dimethylaniline

Guidance literature:: With trifluoroacetic acid; In dichloromethane; at 0 - 20 ℃; Inert atmosphere;

With sodium hydroxide; In methanol; water; at 0 ℃; for 18h; pH=9 - 10; Inert atmosphere;

Reference yield:

: 74115-13-2
5-bromopyridine-3-ol

: 1434047-69-4
(S)-3-((5-(azetidin-2-ylmethoxy)pyridin-3-yl)ethynyl)-5-fluoro-N,N-dimethylaniline

Guidance literature:: Multi-step reaction with 5 steps

1.1: triphenylphosphine / tetrahydrofuran; toluene / 48 h / -10 - 20 °C / Inert atmosphere

2.1: triphenylphosphine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diisopropylamine / toluene / 18 h / 20 - 80 °C / Inert atmosphere

3.1: potassium hydroxide / methanol; water / 16 h / 25 °C

4.1: triphenylphosphine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diisopropylamine / toluene / 16 h / 25 °C

5.1: trifluoroacetic acid / dichloromethane / 5 h / 0 °C / Inert atmosphere

5.2: 18 h / 0 °C / pH 9 - 10

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diisopropylamine; triphenylphosphine; trifluoroacetic acid; potassium hydroxide; In tetrahydrofuran; methanol; dichloromethane; water; toluene; 1.1: |Mitsunobu Displacement / 2.1: |Sonogashira Cross-Coupling / 4.1: |Sonogashira Cross-Coupling;
DOI:10.1021/jm4008455