Ethyl 2-forMylisonicotinate

Base Information

• Chemical Name: Ethyl 2-forMylisonicotinate
• CAS No.: 21908-08-7
• Molecular Formula: C9H9NO3
• Molecular Weight: 179.175
• Hs Code.: 2933399090
• Mol file: 21908-08-7.mol

Synonyms:4-Pyridinecarboxylic acid, 2-formyl-, ethyl ester

Chemical Property of Ethyl 2-forMylisonicotinate

Chemical Property:

• Boiling Point: 288.3±25.0 °C(Predicted)
• PKA: 1.20±0.10(Predicted)
• PSA: 56.26000
• Density: 1.204±0.06 g/cm3(Predicted)
• LogP: 1.07080
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C

Purity/Quality:

99%, ^*data from raw suppliers

Ethyl2-Formylisonicotinate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Ethyl 2-Formylisonicotinate is an intermediate used to synthesize aminoisoindoles as BACE1 inhibitors exhibiting in vivo brain reduction of β-amyloid peptides. It is also used to prepare arylmethylamino analogs of edotecarin as topoisomerase I inhibitors with antitumor activities.

Technology Process of Ethyl 2-forMylisonicotinate

There total 6 articles about Ethyl 2-forMylisonicotinate 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: 81.0%

diethyl pyridine-2,4-dicarboxylate (41438-38-4) → ethyl 2-formylpyridine-4-carboxylate (21908-08-7)

Guidance literature:

diethyl pyridine-2,4-dicarboxylate; With diisobutylaluminium hydride; In tetrahydrofuran; at -78 ℃; for 3h;

With acetic acid; In tetrahydrofuran; water; at 20 ℃; for 1.5h;

Reference yield:

pyridine-2,4-dicarboxylic acid (499-80-9) → ethyl 2-formylpyridine-4-carboxylate (21908-08-7)

Guidance literature:

Multi-step reaction with 2 steps

1: toluene-4-sulfonic acid / 16 h / 80 °C

2: diisobutylaluminium hydride / tetrahydrofuran; toluene / 3.17 h / -78 °C / Inert atmosphere

With diisobutylaluminium hydride; toluene-4-sulfonic acid; In tetrahydrofuran; toluene;

DOI:10.1021/acs.jmedchem.5b01635

Reference yield:

diethyl pyridine-2,4-dicarboxylate (41438-38-4) → pyridine-2,4-dicarbaldehyde (6220-65-1) + ethyl 2-(hydroxymethyl)pyridine-4-carboxylate (31804-60-1) + 4-(hydroxymethyl)pyridine-2-carbaldehyde (212914-74-4) + ethyl 2-formylpyridine-4-carboxylate (21908-08-7)

Guidance literature:

With diisobutylaluminium hydride; In tetrahydrofuran; ethyl acetate; at -20 ℃; for 0.0111111h; Temperature; Time; regioselective reaction; Large scale;

DOI:10.1021/acs.oprd.0c00158

upstream raw materials:

diethyl pyridine-2,4-dicarboxylate

pyridine-2,4-dicarboxylic acid

Downstream raw materials:

KDM5-C70

Refernces

• 1、 Bavetsias, Vassilios,Lanigan, Rachel M.,Ruda, Gian Filippo,Atrash, Butrus,McLaughlin, Mark G.,Tumber, Anthony,Mok, N. Yi,Le Bihan, Yann-Va?,Dempster, Sally,Boxall, Katherine J.,Jeganathan, Fiona,Hatch, Stephanie B.,Savitsky, Pavel,Velupillai, Srikannathasan,Krojer, Tobias,England, Katherine S.,Sejberg, Jimmy,Thai, Ching,Donovan, Adam,Pal, Akos,Scozzafava, Giuseppe,Bennett, James M.,Kawamura, Akane,Johansson, Catrine,Szykowska, Aleksandra,Gileadi, Carina,Burgess-Brown, Nicola A.,Von Delft, Frank,Oppermann, Udo,Walters, Zoe,Shipley, Janet,Raynaud, Florence I.,Westaway, Susan M.,Prinjha, Rab K.,Fedorov, Oleg,Burke, Rosemary,Schofield, Christopher J.,Westwood, Isaac M.,Bountra, Chas,Müller, Susanne,Van Montfort, Rob L. M.,Brennan, Paul E.,Blagg, Julian. "8-Substituted Pyrido[3,4-d]pyrimidin-4(3H)-one Derivatives As Potent, Cell Permeable, KDM4 (JMJD2) and KDM5 (JARID1) Histone Lysine Demethylase Inhibitors". . p. 1388 - 1409. Retrieved 2016.
• 2、 -. "MODULATORS OF METHYL MODIFYING ENZYMES, COMPOSITIONS AND USES THEREOF". Paragraph 0090; 0093; 0094. . Retrieved 2016/09/22.