5-methoxy-1H-pyrrolo[2,3-b]pyridine

Base Information

• Chemical Name: 5-methoxy-1H-pyrrolo[2,3-b]pyridine
• CAS No.: 183208-36-8
• Molecular Formula: C8H8N2O
• Molecular Weight: 148.164
• Hs Code.: 29339900
• DSSTox Substance ID: DTXSID60437878
• Wikidata: Q72489047
• Mol file: 183208-36-8.mol

Synonyms:5-Methoxy-7-azaindole;183208-36-8;5-methoxy-1H-pyrrolo[2,3-b]pyridine;1H-PYRROLO[2,3-B]PYRIDINE, 5-METHOXY-;MFCD06659675;5-methoxyl-7-azaindole;SCHEMBL296198;DTXSID60437878;AFUFCCUQHGSNAN-UHFFFAOYSA-N;BCP09442;CS-B0501;GEO-03788;5-Methoxy-1H-pyrrolo[2,3-b]pyridin;AKOS006293388;AC-9382;PB32442;AS-18176;A4052;AM20061742;FT-0648000;5-Methoxy-1H-pyrrolo[2,3-b]pyridine, AldrichCPR;A812755;W-206308

Chemical Property of 5-methoxy-1H-pyrrolo[2,3-b]pyridine

Chemical Property:

• Refractive Index: 1.647
• Boiling Point: 412.1±45.0 °C(Predicted)
• PKA: 7.24±0.20(Predicted)
• PSA: 37.91000
• Density: 1.244 g/cm³
• LogP: 1.57150
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 148.063662883
• Heavy Atom Count: 11
• Complexity: 140

Purity/Quality:

99% ^*data from raw suppliers

5-Methoxy-7-azaindole ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi,Xn
• Statements: 22
• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CN=C2C(=C1)C=CN2

Technology Process of 5-methoxy-1H-pyrrolo[2,3-b]pyridine

There total 19 articles about 5-methoxy-1H-pyrrolo[2,3-b]pyridine 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: 88.0%

vinyl magnesium bromide (1826-67-1) + 3-methoxy-6-nitropyridine (126739-64-8) → 5-methoxy-1H-pyrrolo[2,3-b]pyridine (183208-36-8)

Guidance literature:

In tetrahydrofuran; at -40 - 20 ℃;

Reference yield: 85.0%

sodium methylate (124-41-4) + 5-bromo-1H-pyrrolo[2,3-b]pyridine (183208-35-7) → 5-methoxy-1H-pyrrolo[2,3-b]pyridine (183208-36-8)

Guidance literature:

With copper(I) bromide; In methanol; N,N-dimethyl-formamide; for 3h; Heating;

DOI:10.1021/ja064310e

Reference yield: 79.0%

2-tert-butoxyamino-3-methyl-5-methoxypyridine + N,N-dimethyl-formamide (68-12-2,33513-42-7) → 5-methoxy-1H-pyrrolo[2,3-b]pyridine (183208-36-8)

Guidance literature:

2-tert-butoxyamino-3-methyl-5-methoxypyridine; With n-butyllithium; In tetrahydrofuran; hexane; at -10 ℃; for 2.5h; Inert atmosphere;

N,N-dimethyl-formamide; In tetrahydrofuran; hexane; at -10 ℃; for 6h; Temperature; Solvent; Reagent/catalyst;

upstream raw materials:

methanol

5-bromo-1H-pyrrolo[2,3-b]pyridine

sodium methylate

7-Azaindole

Downstream raw materials:

3-formyl-5-methoxy-1H-pyrrolo<2,3-b>pyridine

7-azaserotonin

5-hydroxy-1-methyl-1H-pyrrolo[2,3-b]pyridine

5-methoxy-1-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-1H-pyrrolo[2,3-b]pyridine

Refernces

• 1、 -. "AZAINDOLE CARBOXAMIDE COMPOUNDS FOR THE TREATMENT OF MYCOBACTERIAL INFECTIONS". Page/Page column 246. . Retrieved 2021/04/02.
• 2、 -. "5-methoxy-7-azaindole synthesis method". Paragraph 0231; 0235-0236. . Retrieved 2019/10/01.