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

Base Information

• Chemical Name: 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
• CAS No.: 868660-40-6
• Molecular Formula: C₂₂H₂₂FN₃O₃
• Molecular Weight: 395.433

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

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Technology Process of 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

There total 13 articles about 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 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: 53.0%

1-(4-fluorobenzyl)-4-(2-hydroxyethyl)-N-(tetrahydro-2H-pyran-2-yloxy)-1H-pyrrolo[2,3-c]pyridine-5-carboxamide (868660-39-3) → 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 (868660-40-6)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; p-toluenesulfonyl chloride; In dichloromethane; at 20 ℃; Product distribution / selectivity; Heating / reflux;

Reference yield:

2-methyl-1H-pyrrole-3-carboxylic acid ethyl ester (936-12-9) → 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 (868660-40-6)

Guidance literature:

Multi-step reaction with 12 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

11.1: lithium hexamethyldisilazane / tetrahydrofuran / Heating

12.1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 20 °C

With bis-triphenylphosphine-palladium(II) chloride; N-Bromosuccinimide; di-isopropyl azodicarboxylate; 5 % alumina-supported palladium; palladium 10% on activated carbon; potassium tert-butylate; hydrogen; acetic acid; triethylamine; triphenylphosphine; lithium chloride; lithium hydroxide; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; 7.1: Stille coupling / 12.1: Mitsunobu closure;

DOI:10.1021/jm200208d

Reference yield:

7-(4-fluorobenzyl)pyrano[3,4-b]pyrrolo[3,2-d]pyridin-4(7H)-one (868660-36-0) → 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 (868660-40-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 5 % alumina-supported palladium; hydrogen / tetrahydrofuran; methanol; water / 18 h / 1810.07 Torr / Inert atmosphere

2: lithium hexamethyldisilazane / tetrahydrofuran / Heating

3: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 20 °C

With di-isopropyl azodicarboxylate; 5 % alumina-supported palladium; hydrogen; triphenylphosphine; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; water; 3: Mitsunobu closure;

DOI:10.1021/jm200208d

upstream raw materials:

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

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

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

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

Downstream raw materials:

1-[(dimethylamino)methyl]-3-(4-fluorobenzyl)-7-(tetrahydro-2H-pyran-2-yloxy)-3,7,8,9-tetrahydro-6H-pyrrolo[2,3-c]-1,7-naphthyridin-6-one

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