ethyl 5-nitro-8-phenyl-1-(tetrahydro-2H-pyran-2-yl)-1,6-dihydropyrrolo[2,3-g]indazole-7-carboxylate

Base Information

• Chemical Name: ethyl 5-nitro-8-phenyl-1-(tetrahydro-2H-pyran-2-yl)-1,6-dihydropyrrolo[2,3-g]indazole-7-carboxylate
• CAS No.: 1334218-33-5
• Molecular Formula: C₂₃H₂₂N₄O₅
• Molecular Weight: 434.451
• Mol file: 1334218-33-5.mol

Synonyms:ethyl 5-nitro-8-phenyl-1-(tetrahydro-2H-pyran-2-yl)-1,6-dihydropyrrolo[2,3-g]indazole-7-carboxylate

Chemical Property of ethyl 5-nitro-8-phenyl-1-(tetrahydro-2H-pyran-2-yl)-1,6-dihydropyrrolo[2,3-g]indazole-7-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl 5-nitro-8-phenyl-1-(tetrahydro-2H-pyran-2-yl)-1,6-dihydropyrrolo[2,3-g]indazole-7-carboxylate

There total 2 articles about ethyl 5-nitro-8-phenyl-1-(tetrahydro-2H-pyran-2-yl)-1,6-dihydropyrrolo[2,3-g]indazole-7-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: 86.0%

7-iodo-5-nitro-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-6-amine (1334217-96-7) + phenylpropynoic acid ethyl ester (2216-94-6) → ethyl 5-nitro-8-phenyl-1-(tetrahydro-2H-pyran-2-yl)-1,6-dihydropyrrolo[2,3-g]indazole-7-carboxylate (1334218-33-5)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate; XPhos; In tetrahydrofuran; for 16h; regioselective reaction; Reflux; Inert atmosphere;

DOI:10.1016/j.tet.2011.07.029

Reference yield:

6-nitroindazole (7597-18-4) → ethyl 5-nitro-8-phenyl-1-(tetrahydro-2H-pyran-2-yl)-1,6-dihydropyrrolo[2,3-g]indazole-7-carboxylate (1334218-33-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: sulfuric acid; potassium nitrate

2.1: sulfuric acid / dichloromethane

3.1: palladium 10% on activated carbon; cyclohexa-1,4-diene / methanol / 3 h / Reflux

3.2: 1 h / 20 °C

4.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate; XPhos / tetrahydrofuran / 16 h / Reflux; Inert atmosphere

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; cyclohexa-1,4-diene; sulfuric acid; palladium 10% on activated carbon; potassium carbonate; potassium nitrate; XPhos; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1016/j.tet.2011.07.029

Reference yield: 88.0%

ethyl 5-nitro-8-phenyl-1-(tetrahydro-2H-pyran-2-yl)-1,6-dihydropyrrolo[2,3-g]indazole-7-carboxylate (1334218-33-5) → C18H14N4O4 (1429219-59-9)

Guidance literature:

With toluene-4-sulfonic acid; In ethanol; water; for 16h; Reflux;

DOI:10.1016/j.bmcl.2013.02.074

upstream raw materials:

7-iodo-5-nitro-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-6-amine

phenylpropynoic acid ethyl ester

6-nitroindazole

Downstream raw materials:

5-nitro-8-phenyl-1,6-dihydropyrrolo[2,3-g]indazole

C₁₈H₁₄N₄O₄

C₁₈H₁₆N₄O₂