6-Fluoro-1H-pyrrolo[3,2-b]pyridin-2(3H)-one

Base Information

• Chemical Name: 6-Fluoro-1H-pyrrolo[3,2-b]pyridin-2(3H)-one
• CAS No.: 136888-22-7
• Molecular Formula: C7H5FN2O
• Molecular Weight: 152.128
• DSSTox Substance ID: DTXSID001224873
• Mol file: 136888-22-7.mol

Synonyms:136888-22-7;6-Fluoro-1H-pyrrolo[3,2-b]pyridin-2(3H)-one;6-Fluoro-4-azaoxindole;6-fluoro-1,3-dihydropyrrolo[3,2-b]pyridin-2-one;2H-Pyrrolo[3,2-b]pyridin-2-one, 6-fluoro-1,3-dihydro-;2H-Pyrrolo[3,2-b]pyridin-2-one,6-fluoro-1,3-dihydro-(9CI);6-Fluoro-1,3-dihydro-2H-pyrrolo[3,2-b]pyridin-2-one;6-fluoro-4-aza-2-oxindole;6-fluoro-1H,2H,3H-pyrrolo[3,2-b]pyridin-2-one;SCHEMBL659190;IXVQXCSKTPIMLA-UHFFFAOYSA-N;2H-Pyrrolo[3,2-B]pyridine-2-one, 6-Fluoro-1,3-DIHYDRO-;DTXSID001224873;AMY23747;MFCD12963049;AKOS022186482;s11339;AS-69344;CS-0445566

Chemical Property of 6-Fluoro-1H-pyrrolo[3,2-b]pyridin-2(3H)-one

Chemical Property:

• Boiling Point: 289.4±40.0 °C(Predicted)
• PKA: 12.01±0.20(Predicted)
• PSA: 41.99000
• Density: 1.402±0.06 g/cm3(Predicted)
• LogP: 0.85330
• Storage Temp.: 2-8°C
• XLogP3: -0.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 152.03859095
• Heavy Atom Count: 11
• Complexity: 185

Purity/Quality:

97% ^*data from raw suppliers

6-Fluoro-1H-pyrrolo[3,2-b]pyridin-2(3H)-one 95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C2=C(C=C(C=N2)F)NC1=O

Technology Process of 6-Fluoro-1H-pyrrolo[3,2-b]pyridin-2(3H)-one

There total 7 articles about 6-Fluoro-1H-pyrrolo[3,2-b]pyridin-2(3H)-one 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:

2-bis(ethoxycarbonyl)methyl-5-fluoro-3-nitropyridine (136888-23-8) + diethyl malonate (105-53-3) → 6-fluoro-1,3-dihydro-2H-pyrrolo[3,2-b]pyridin-2-one (136888-22-7) + 3-amino-2-bis(ethoxycarbonyl)methyl-5-fluoropyridine (136888-24-9)

Guidance literature:

aluminum nickel; In hydrogenchloride; ethanol; water;

Reference yield:

2-bis(ethoxycarbonyl)methyl-5-fluoro-3-nitropyridine (136888-23-8) + diethyl malonate (105-53-3) → 3-amino-2-bis-(ethoxycarbonyl)methyl-5-fluoropyridine + 6-fluoro-1,3-dihydro-2H-pyrrolo[3,2-b]pyridin-2-one (136888-22-7)

Guidance literature:

aluminum nickel; In hydrogenchloride; ethanol; water;

Reference yield:

5-fluoropyridin-2-ol (51173-05-8) → 6-fluoro-1,3-dihydro-2H-pyrrolo[3,2-b]pyridin-2-one (136888-22-7)

Guidance literature:

Multi-step reaction with 5 steps

1: 11 percent / conc. H₂SO₄, HNO₃ / 3.5 h / 55 - 60 °C

2: 37 percent / PCl₅, POCl₃ / 100 °C

3: 1.) NaH / 1.) DMF, RT, 0.25 h, 2.) DMF, 0 deg C, 0.25 h

4: H₂ / Raney nickel / aq. ethanol / 2280 Torr

5: 6 N HCl / 3 h / Heating

With hydrogenchloride; phosphorus pentachloride; sulfuric acid; hydrogen; nitric acid; sodium hydride; trichlorophosphate; nickel; In ethanol;

DOI:10.1002/jhet.5570330213

upstream raw materials:

3-amino-2-bis(ethoxycarbonyl)methyl-5-fluoropyridine

5-fluoropyridin-2-ol

5-fluoro-2-hydroxy-3-nitropyridine

2-chloro-5-fluoro-3-nitro pyridine

Downstream raw materials:

E/Z-3-(3-chloro-2-fluorobenzylidene)-6-fluoro-1,3-dihydropyrrolo[3,2-b]pyridin-2-one