Methyl 6-chloro-1H-pyrrolo[2,3-b]pyridine-4-carboxylate

Base Information

• Chemical Name: Methyl 6-chloro-1H-pyrrolo[2,3-b]pyridine-4-carboxylate
• CAS No.: 1190312-37-8
• Molecular Formula: C9H7ClN2O2
• Molecular Weight: 210.62
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID50696659
• Wikidata: Q82626331
• Mol file: 1190312-37-8.mol

Synonyms:1190312-37-8;Methyl 6-chloro-1H-pyrrolo[2,3-b]pyridine-4-carboxylate;6-CHLORO-7-AZAINDOLE-4-CARBOXYLIC ACID METHYL ESTER;1H-Pyrrolo[2,3-b]pyridine-4-carboxylic acid, 6-chloro-, methyl ester;SCHEMBL2158555;AMY9882;DTXSID50696659;FNKIBYKKYBUANQ-UHFFFAOYSA-N;6-chloro-1H-pyrrolo[2,3-b]pyridine-4-carboxylic acid methyl ester;AKOS016010828;SB14232;AS-77052;CS-0004468;FT-0763988;P11541;A892743;Methyl6-chloro-1H-pyrrolo[2,3-b]pyridine-4-carboxylate

Chemical Property of Methyl 6-chloro-1H-pyrrolo[2,3-b]pyridine-4-carboxylate

Chemical Property:

• PKA: 11.78±0.40(Predicted)
• PSA: 54.98000
• Density: 1.453±0.06 g/cm3(Predicted)
• LogP: 2.00290
• Storage Temp.: 2-8°C
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 210.0196052
• Heavy Atom Count: 14
• Complexity: 237

Purity/Quality:

97% ^*data from raw suppliers

Methyl6-Chloro-1H-pyrrolo[2,3-b]pyridine-4-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1=CC(=NC2=C1C=CN2)Cl

Technology Process of Methyl 6-chloro-1H-pyrrolo[2,3-b]pyridine-4-carboxylate

There total 3 articles about Methyl 6-chloro-1H-pyrrolo[2,3-b]pyridine-4-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:

4-(methoxycarbonyl)-1H-pyrrolo[2,3-b]pyridine 7-oxide (1201748-37-9) → methyl 6-chloro-1H-pyrrolo[2,3-b]pyridine-4-carboxylate (1190312-37-8)

Guidance literature:

With chloroformic acid ethyl ester; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; at 50 ℃; for 16h; Inert atmosphere;

DOI:10.1016/j.bmc.2011.04.014

Reference yield:

methyl 1H-pyrrolo[2,3-b]pyridine-4-carboxylate (351439-07-1) → methyl 6-chloro-1H-pyrrolo[2,3-b]pyridine-4-carboxylate (1190312-37-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 3-chloro-benzenecarboperoxoic acid / 1,2-dimethoxyethane / 22.5 h / 20 °C / Inert atmosphere

2: chloroformic acid ethyl ester; 1,1,1,3,3,3-hexamethyl-disilazane / tetrahydrofuran / 16 h / 50 °C / Inert atmosphere

With chloroformic acid ethyl ester; 3-chloro-benzenecarboperoxoic acid; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; 1,2-dimethoxyethane;

DOI:10.1016/j.bmc.2011.04.014

Reference yield:

1H-pyrrolo[2,3-b]pyridine-4-carboxylic acid (479553-01-0) → methyl 6-chloro-1H-pyrrolo[2,3-b]pyridine-4-carboxylate (1190312-37-8)

Guidance literature:

Multi-step reaction with 3 steps

1: methanol; hexane; dichloromethane / 0.5 h / 20 °C / Inert atmosphere

2: 3-chloro-benzenecarboperoxoic acid / 1,2-dimethoxyethane / 22.5 h / 20 °C / Inert atmosphere

3: chloroformic acid ethyl ester; 1,1,1,3,3,3-hexamethyl-disilazane / tetrahydrofuran / 16 h / 50 °C / Inert atmosphere

With chloroformic acid ethyl ester; 3-chloro-benzenecarboperoxoic acid; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; hexane; dichloromethane;

DOI:10.1016/j.bmc.2011.04.014

upstream raw materials:

1H-pyrrolo[2,3-b]pyridine-4-carboxylic acid

4-(methoxycarbonyl)-1H-pyrrolo[2,3-b]pyridine 7-oxide

methyl 1H-pyrrolo[2,3-b]pyridine-4-carboxylate

Downstream raw materials:

6-phenyl-1H-pyrrolo[2,3-b]pyridine-4-carboxylic acid

tert-butyl [(trans-4-((6-phenyl-1H-pyrrolo[2,3-b]pyridine-4-carboxamido)methyl)cyclohexyl)methyl]carbamate

methyl 6-phenyl-1H-pyrrolo[2,3-b]pyridine-4-carboxylate

6-chloro-1H-pyrrolo[2,3-b]pyridine-4-carboxylic acid