(S)-tert-butyl 2-((5-(phenylethynyl)pyridin-3-yloxy)methyl)azetidine-1-carboxylate

Base Information

Chemical Name:(S)-tert-butyl 2-((5-(phenylethynyl)pyridin-3-yloxy)methyl)azetidine-1-carboxylate
CAS No.:1434047-75-2
Molecular Formula:C₂₂H₂₄N₂O₃
Molecular Weight:364.444
Hs Code.:

Synonyms:(S)-tert-butyl 2-((5-(phenylethynyl)pyridin-3-yloxy)methyl)azetidine-1-carboxylate

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Chemical Property of (S)-tert-butyl 2-((5-(phenylethynyl)pyridin-3-yloxy)methyl)azetidine-1-carboxylate

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Technology Process of (S)-tert-butyl 2-((5-(phenylethynyl)pyridin-3-yloxy)methyl)azetidine-1-carboxylate

There total 7 articles about (S)-tert-butyl 2-((5-(phenylethynyl)pyridin-3-yloxy)methyl)azetidine-1-carboxylate 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: 54.0%

: 591-50-4
iodobenzene

: 186593-31-7
(S)-2-(5-bromo-pyridin-3-yloxymethyl)-azetidine-1-carboxylic acid tert-butyl ester

: 1066-54-2
trimethylsilylacetylene

: 1434047-75-2
(S)-tert-butyl 2-((5-(phenylethynyl)pyridin-3-yloxy)methyl)azetidine-1-carboxylate

Guidance literature:: (S)-2-(5-bromo-pyridin-3-yloxymethyl)-azetidine-1-carboxylic acid tert-butyl ester; trimethylsilylacetylene; With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diisopropylamine; triphenylphosphine; In toluene; at 20 - 80 ℃; for 18h; Inert atmosphere;

With water; potassium hydroxide; In methanol; toluene; at 25 ℃; for 3h;

iodobenzene; In methanol; toluene; at 80 ℃; for 16h;

Reference yield: 54.0%

: 591-50-4
iodobenzene

: 1222139-46-9
(S)-tert-butyl 2-((5-ethynylpyridin-3-yloxy)methyl)azetidine-1-carboxylate

: 1434047-75-2
(S)-tert-butyl 2-((5-(phenylethynyl)pyridin-3-yloxy)methyl)azetidine-1-carboxylate

Guidance literature:: With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diisopropylamine; triphenylphosphine; In toluene; at 25 ℃; for 18h;
DOI:10.1021/jm4008455

Reference yield:

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

: 1434047-75-2
(S)-tert-butyl 2-((5-(phenylethynyl)pyridin-3-yloxy)methyl)azetidine-1-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

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

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

2.2: 3 h / 25 °C

2.3: 16 h / 80 °C

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diisopropylamine; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; toluene; 1.1: |Mitsunobu Displacement / 2.1: |Sonogashira Cross-Coupling;