(R)-tert-butyl 2-((5-bromopyridin-3-yloxy)methyl)azetidine-1-carboxylate

Base Information

• Chemical Name: (R)-tert-butyl 2-((5-bromopyridin-3-yloxy)methyl)azetidine-1-carboxylate
• CAS No.: 228867-09-2
• Molecular Formula: C₁₄H₁₉BrN₂O₃
• Molecular Weight: 343.22
• Mol file: 228867-09-2.mol

Synonyms:(R)-tert-butyl 2-((5-bromopyridin-3-yloxy)methyl)azetidine-1-carboxylate

Chemical Property of (R)-tert-butyl 2-((5-bromopyridin-3-yloxy)methyl)azetidine-1-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-tert-butyl 2-((5-bromopyridin-3-yloxy)methyl)azetidine-1-carboxylate

There total 1 articles about (R)-tert-butyl 2-((5-bromopyridin-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: 30.0%

5-bromopyridine-3-ol (74115-13-2) + (R)-1-t-butyloxycarbonyl-2-azetidinemethanol (161511-90-6) → (R)-tert-butyl 2-((5-bromopyridin-3-yloxy)methyl)azetidine-1-carboxylate (228867-09-2)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; toluene; at -10 ℃; for 48h;

DOI:10.1021/jm4008455

Reference yield: 37.0%

(R)-tert-butyl 2-((5-bromopyridin-3-yloxy)methyl)azetidine-1-carboxylate (228867-09-2) + hexamethyldistannane (661-69-8) → 3-[[1-(tert-butoxycarbonyl)-2(R)-azetidinyl]methoxy]-5-(trimethylstannyl)pyridine (1222138-49-9,213766-21-3)

Guidance literature:

tetrakis(triphenylphosphine) palladium⁽⁰⁾; In toluene; at 90 ℃; for 26h;

Reference yield:

(R)-tert-butyl 2-((5-bromopyridin-3-yloxy)methyl)azetidine-1-carboxylate (228867-09-2) → (R)-3-(azetidin-2-ylmethoxy)-5-(phenylethynyl)pyridine (1434047-74-1)

Guidance literature:

Multi-step reaction with 4 steps

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

2.1: potassium hydroxide / methanol; water / 18 h / 80 °C

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

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

4.2: 18 h / 0 °C / pH 9 - 10

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diisopropylamine; triphenylphosphine; trifluoroacetic acid; potassium hydroxide; In methanol; dichloromethane; water; toluene; 1.1: |Sonogashira Cross-Coupling / 3.1: |Sonogashira Cross-Coupling;

DOI:10.1021/jm4008455

upstream raw materials:

5-bromopyridine-3-ol

(R)-1-t-butyloxycarbonyl-2-azetidinemethanol

Downstream raw materials:

3-[[1-(tert-butoxycarbonyl)-2(R)-azetidinyl]methoxy]-5-(trimethylstannyl)pyridine

(R)-3-(azetidin-2-ylmethoxy)-5-(phenylethynyl)pyridine

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