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

Base Information

• Chemical Name: 5-nitro-1H-pyrrolo[2,3-b]pyridine
• CAS No.: 101083-92-5
• Molecular Formula: C7H5N3O2
• Molecular Weight: 163.136
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID80467950
• Wikidata: Q72494258
• Mol file: 101083-92-5.mol

Synonyms:5-nitro-1H-pyrrolo[2,3-b]pyridine;5-Nitro-7-azaindole;101083-92-5;1H-PYRROLO[2,3-B]PYRIDINE, 5-NITRO-;MFCD06659682;SCHEMBL1365382;DTXSID80467950;INMIPMLIYKQQID-UHFFFAOYSA-N;BCP27868;CS-B0505;AKOS006293389;PB15855;DS-10666;SY097773;AM20050609;FT-0648835;A16247;W-200645

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

Chemical Property:

• Melting Point: 280℃
• Refractive Index: 1.741
• Boiling Point: 392.8±35.0 °C(Predicted)
• PKA: 0.65±0.20(Predicted)
• PSA: 74.50000
• Density: 1.525 g/cm³
• LogP: 1.99430
• Storage Temp.: 2-8°C
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 163.038176411
• Heavy Atom Count: 12
• Complexity: 192

Purity/Quality:

98% ^*data from raw suppliers

5-Nitro-1H-pyrrolo[2,3-b]pyridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CNC2=NC=C(C=C21)[N+](=O)[O-]
• Uses: 5-Nitro-1H-pyrrolo[2,3-b]pyridine is a reagent used in the synthesis of Cdc7 kinase inhibitors used as a novel cancer therapy. Also an intermediate in the synthesis of 4-anilinoquinazolines as potential anticancer agents.

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

There total 8 articles about 5-nitro-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: 87.8%

2-amino-5-nitro-3-[(trimethylsilyl)ethynyl]pyridine (869884-26-4) → 5-nitro-1H-pyrrolo[2,3-b]pyridine (101083-92-5)

Guidance literature:

With morpholine; In water; at 90 ℃; for 24h; Reagent/catalyst; Temperature; Solvent; Large scale;

DOI:10.1021/acs.oprd.5b00181

Reference yield: 85.0%

5-nitro-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine (937012-11-8) → 5-nitro-1H-pyrrolo[2,3-b]pyridine (101083-92-5)

Guidance literature:

With sodium hydroxide; In methanol; dichloromethane; at 20 ℃; for 1h;

Reference yield: 51.0%

5-nitro-7-azaindoline (118600-53-6) → 5-nitro-1H-pyrrolo[2,3-b]pyridine (101083-92-5)

Guidance literature:

With manganese(IV) oxide; In toluene; for 6h; Heating;

DOI:10.1055/s-2005-872088

upstream raw materials:

5-nitro-7-azaindoline

2-amino-5-nitro-3-[(trimethylsilyl)ethynyl]pyridine

3-iodo-5-nitropyridin-2-ylamine

7-Azaindole

Downstream raw materials:

1H-pyrrolo[2,3-b]pyridin-5-amine

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

5-nitro-1-(p-tolylsulfonyl)pyrrolo[2,3-b]pyridine

9-(1-benzyl-3,6-dihydro-2H-pyridin-5-yl)-3H-pyrrolo[3,2-f][1,7]naphthyridine

Refernces

• 1、 -. "HEAT SHOCK PROTEIN 90 INHIBITORS". Page/Page column 24; 33; 35; 73. . Retrieved 2018/10/19.
• 2、 -. "HETEROARYL DERIVATIVES AS PROTEIN KINASE INHIBITORS". Page/Page column 41; 27. . Retrieved 2010/11/30.