(1S)-[2-(5-bromopyridin-3-yloxy)-1-hydroxymethyl-ethyl]carbamic acid tert-butyl ester

Base Information

• Chemical Name: (1S)-[2-(5-bromopyridin-3-yloxy)-1-hydroxymethyl-ethyl]carbamic acid tert-butyl ester
• CAS No.: 552332-01-1
• Molecular Formula: C₁₃H₁₉BrN₂O₄
• Molecular Weight: 347.209

Synonyms:(1S)-[2-(5-bromopyridin-3-yloxy)-1-hydroxymethyl-ethyl]carbamic acid tert-butyl ester

Chemical Property of (1S)-[2-(5-bromopyridin-3-yloxy)-1-hydroxymethyl-ethyl]carbamic acid tert-butyl ester

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Technology Process of (1S)-[2-(5-bromopyridin-3-yloxy)-1-hydroxymethyl-ethyl]carbamic acid tert-butyl ester

There total 1 articles about (1S)-[2-(5-bromopyridin-3-yloxy)-1-hydroxymethyl-ethyl]carbamic acid tert-butyl ester 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:

5-bromopyridine-3-ol (74115-13-2) → (1S)-[2-(5-bromopyridin-3-yloxy)-1-hydroxymethyl-ethyl]carbamic acid tert-butyl ester (552332-01-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 99 percent / Ph₃P; diethyl azodicarboxylate / tetrahydrofuran / 0 - 20 °C

2: 93 percent / TBAF / tetrahydrofuran / 1 h / 20 °C

With tetrabutyl ammonium fluoride; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; 1: Mitsunobu coupling;

DOI:10.1021/jm0701019

Reference yield:

(1S)-[2-(5-bromopyridin-3-yloxy)-1-hydroxymethyl-ethyl]carbamic acid tert-butyl ester (552332-01-1) → (1S)-1-(2-fluoro-4-trifluoromethylbenzyl)-2-[5-(3-methyl-1H-indazol-5-yl)pyridin-3-yloxy]ethylamine tristrifluoroacetate

Guidance literature:

Multi-step reaction with 4 steps

1: 92 percent / diethyl azodicarboxylate; Ph₃P / tetrahydrofuran / 4 - 20 °C

2: 65 percent / Et₃N / Pd₂(dba)3; tri-o-tolylphosphine / dimethylformamide / 4 h / 72 °C

3: CuBr*SMe₂ / tetrahydrofuran / 0.67 h / -35 - -20 °C

4: CH₂Cl₂ / 0 - 20 °C

With triethylamine; triphenylphosphine; diethylazodicarboxylate; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; copper(I) bromide dimethylsulfide complex; tris-(o-tolyl)phosphine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 1: Mitsunobu reaction / 2: Stille coupling;

DOI:10.1021/jm0701019

Reference yield:

(1S)-[2-(5-bromopyridin-3-yloxy)-1-hydroxymethyl-ethyl]carbamic acid tert-butyl ester (552332-01-1) → C38H42N4O5

Guidance literature:

Multi-step reaction with 3 steps

1: 92 percent / diethyl azodicarboxylate; Ph₃P / tetrahydrofuran / 4 - 20 °C

2: 65 percent / Et₃N / Pd₂(dba)3; tri-o-tolylphosphine / dimethylformamide / 4 h / 72 °C

3: CuBr*SMe₂ / tetrahydrofuran / 0.67 h / -35 - -20 °C

With triethylamine; triphenylphosphine; diethylazodicarboxylate; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; copper(I) bromide dimethylsulfide complex; tris-(o-tolyl)phosphine; In tetrahydrofuran; N,N-dimethyl-formamide; 1: Mitsunobu reaction / 2: Stille coupling;

DOI:10.1021/jm0701019

upstream raw materials:

5-bromopyridine-3-ol

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