7-(4-fluorobenzyl)-1,7-dihydropyrano[3,4-b]pyrrolo[3,2-d]pyridin-4(2H)-one

Base Information

• Chemical Name: 7-(4-fluorobenzyl)-1,7-dihydropyrano[3,4-b]pyrrolo[3,2-d]pyridin-4(2H)-one
• CAS No.: 868660-37-1
• Molecular Formula: C₁₇H₁₃FN₂O₂
• Molecular Weight: 296.301
• Mol file: 868660-37-1.mol

Synonyms:7-(4-fluorobenzyl)-1,7-dihydropyrano[3,4-b]pyrrolo[3,2-d]pyridin-4(2H)-one

Chemical Property of 7-(4-fluorobenzyl)-1,7-dihydropyrano[3,4-b]pyrrolo[3,2-d]pyridin-4(2H)-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 7-(4-fluorobenzyl)-1,7-dihydropyrano[3,4-b]pyrrolo[3,2-d]pyridin-4(2H)-one

There total 11 articles about 7-(4-fluorobenzyl)-1,7-dihydropyrano[3,4-b]pyrrolo[3,2-d]pyridin-4(2H)-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: 81.0%

7-(4-fluorobenzyl)pyrano[3,4-b]pyrrolo[3,2-d]pyridin-4(7H)-one (868660-36-0) → 7-(4-fluorobenzyl)-1,7-dihydropyrano[3,4-b]pyrrolo[3,2-d]pyridin-4(2H)-one (868660-37-1)

Guidance literature:

With 5 % alumina-supported palladium; hydrogen; In tetrahydrofuran; methanol; water; for 18h; under 1810.07 Torr; Inert atmosphere;

DOI:10.1021/jm200208d

Reference yield:

2-methyl-1H-pyrrole-3-carboxylic acid ethyl ester (936-12-9) → 7-(4-fluorobenzyl)-1,7-dihydropyrano[3,4-b]pyrrolo[3,2-d]pyridin-4(2H)-one (868660-37-1)

Guidance literature:

Multi-step reaction with 10 steps

1.1: potassium tert-butylate / tetrahydrofuran / 1.5 h / Inert atmosphere

1.2: 16.75 h / 20 °C / Inert atmosphere

2.1: N-Bromosuccinimide / ethyl acetate / 1.75 h / 20 °C

2.2: 1.5 h / Reflux

3.1: potassium tert-butylate / tetrahydrofuran / 0.5 h

3.2: 17 h / 20 °C

4.1: lithium hexamethyldisilazane / tetrahydrofuran / 2.5 h / -78 °C / Inert atmosphere

5.1: palladium 10% on activated carbon; hydrogen; triethylamine / methanol / 1 h / 2068.65 Torr / Inert atmosphere

6.1: triethylamine / dichloromethane / 0 °C

7.1: bis-triphenylphosphine-palladium(II) chloride; lithium chloride / N,N-dimethyl-formamide / 18 h / 60 °C / Inert atmosphere

8.1: lithium hydroxide / methanol; water / 5 h / 60 °C

9.1: acetic acid / 6 h / Reflux

10.1: 5 % alumina-supported palladium; hydrogen / tetrahydrofuran; methanol; water / 18 h / 1810.07 Torr / Inert atmosphere

With bis-triphenylphosphine-palladium(II) chloride; N-Bromosuccinimide; 5 % alumina-supported palladium; palladium 10% on activated carbon; potassium tert-butylate; hydrogen; acetic acid; triethylamine; lithium chloride; lithium hydroxide; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; 7.1: Stille coupling;

DOI:10.1021/jm200208d

Reference yield:

lithium (Z)-4-(2-ethoxyvinyl)-1-(4-fluorobenzyl)-1H-pyrrolo[2,3-c]pyridine-5-carboxylate → 7-(4-fluorobenzyl)-1,7-dihydropyrano[3,4-b]pyrrolo[3,2-d]pyridin-4(2H)-one (868660-37-1)

Guidance literature:

Multi-step reaction with 2 steps

1: acetic acid / 6 h / Reflux

2: 5 % alumina-supported palladium; hydrogen / tetrahydrofuran; methanol; water / 18 h / 1810.07 Torr / Inert atmosphere

With 5 % alumina-supported palladium; hydrogen; acetic acid; In tetrahydrofuran; methanol; water;

DOI:10.1021/jm200208d

upstream raw materials:

7-(4-fluorobenzyl)pyrano[3,4-b]pyrrolo[3,2-d]pyridin-4(7H)-one

2-methyl-1H-pyrrole-3-carboxylic acid ethyl ester

ethyl 1-(4-fluorobenzyl)-2-methyl-1H-pyrrole-3-carboxylate

ethyl 4,5-dibromo-2-(bromomethyl)-1-(4-fluorobenzyl)-1H-pyrrole-3-carboxylate

Downstream raw materials:

1-(4-fluorobenzyl)-4-(2-hydroxyethyl)-N-(tetrahydro-2H-pyran-2-yloxy)-1H-pyrrolo[2,3-c]pyridine-5-carboxamide

1-(4-fluorobenzyl)-4-(2-hydroxyethyl)-N-{[2-(trimethylsilyl)ethoxy]methoxy}-1H-pyrrolo[2,3-c]pyridine-5-carboxamide

3-[(4-fluorophenyl)methyl]-3,7,8,9-tetrahydro-7-[(tetrahydro-2H-pyran-2-yl)oxy]-6H-pyrrolo[2,3-c][1,7]naphthyridin-6-one

7-(4-fluorobenzyl)-4-oxo-1,2,4,7-tetrahydropyrano[3,4-b]pyrrolo[3,2-d]pyridine-9-sulfonyl chloride