3-(4-fluorobenzyl)-1-(3-(N-methyl-acetamido)-prop-1-yn-1-yl)-7-{[2-(trimethylsilyl)ethoxy]methoxy}-3,7,8,9-tetrahydro-6H-pyrrolo[ 2,3-c]-1,7-naphthyridin-6-one

Base Information

• Chemical Name: 3-(4-fluorobenzyl)-1-(3-(N-methyl-acetamido)-prop-1-yn-1-yl)-7-{[2-(trimethylsilyl)ethoxy]methoxy}-3,7,8,9-tetrahydro-6H-pyrrolo[ 2,3-c]-1,7-naphthyridin-6-one
• CAS No.: 1293388-54-1
• Molecular Formula: C₂₉H₃₅FN₄O₄Si
• Molecular Weight: 550.705
• Mol file: 1293388-54-1.mol

Synonyms:3-(4-fluorobenzyl)-1-(3-(N-methyl-acetamido)-prop-1-yn-1-yl)-7-{[2-(trimethylsilyl)ethoxy]methoxy}-3,7,8,9-tetrahydro-6H-pyrrolo[ 2,3-c]-1,7-naphthyridin-6-one

Chemical Property of 3-(4-fluorobenzyl)-1-(3-(N-methyl-acetamido)-prop-1-yn-1-yl)-7-{[2-(trimethylsilyl)ethoxy]methoxy}-3,7,8,9-tetrahydro-6H-pyrrolo[ 2,3-c]-1,7-naphthyridin-6-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-(4-fluorobenzyl)-1-(3-(N-methyl-acetamido)-prop-1-yn-1-yl)-7-{[2-(trimethylsilyl)ethoxy]methoxy}-3,7,8,9-tetrahydro-6H-pyrrolo[ 2,3-c]-1,7-naphthyridin-6-one

There total 15 articles about 3-(4-fluorobenzyl)-1-(3-(N-methyl-acetamido)-prop-1-yn-1-yl)-7-{[2-(trimethylsilyl)ethoxy]methoxy}-3,7,8,9-tetrahydro-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: 96.0%

3-(4-fluorobenzyl)-1-iodo-7-{[2-(trimethylsilyl)ethoxy]methoxy}-8,9-dihydro-3H-pyrrolo[2,3-c][1,7]naphthyridin-6(7H)-one (1161880-19-8) + N-methyl-N-(2-propynyl)acetamide (18341-31-6) → 3-(4-fluorobenzyl)-1-(3-(N-methyl-acetamido)-prop-1-yn-1-yl)-7-{[2-(trimethylsilyl)ethoxy]methoxy}-3,7,8,9-tetrahydro-6H-pyrrolo[ 2,3-c]-1,7-naphthyridin-6-one (1293388-54-1)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; In N,N-dimethyl-formamide;

DOI:10.1021/jm200208d

Reference yield:

2-methyl-1H-pyrrole-3-carboxylic acid ethyl ester (936-12-9) → 3-(4-fluorobenzyl)-1-(3-(N-methyl-acetamido)-prop-1-yn-1-yl)-7-{[2-(trimethylsilyl)ethoxy]methoxy}-3,7,8,9-tetrahydro-6H-pyrrolo[ 2,3-c]-1,7-naphthyridin-6-one (1293388-54-1)

Guidance literature:

Multi-step reaction with 11 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: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; N-Methyldicyclohexylamine; lithium chloride; tri tert-butylphosphoniumtetrafluoroborate / 1,4-dioxane / 1 h / 70 °C / Inert atmosphere

8.1: toluene-4-sulfonic acid / tetrahydrofuran / 60 h

9.1: sodium cyanoborohydride; acetic acid / 2 h / 20 °C

10.1: N-iodo-succinimide / N,N-dimethyl-formamide / 1 h / 20 °C

11.1: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triethylamine / N,N-dimethyl-formamide

With bis-triphenylphosphine-palladium(II) chloride; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; N-Bromosuccinimide; N-iodo-succinimide; copper(l) iodide; N-Methyldicyclohexylamine; palladium 10% on activated carbon; potassium tert-butylate; hydrogen; sodium cyanoborohydride; toluene-4-sulfonic acid; acetic acid; triethylamine; lithium chloride; lithium hexamethyldisilazane; tri tert-butylphosphoniumtetrafluoroborate; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; 11.1: Sonogashira coupling;

DOI:10.1021/jm200208d

Reference yield:

methyl 4-[(E)-2-butoxyvinyl]-1-(4-fluorobenzyl)-1H-pyrrolo[2,3-c]pyridine-5-carboxylate (934621-80-4) → 3-(4-fluorobenzyl)-1-(3-(N-methyl-acetamido)-prop-1-yn-1-yl)-7-{[2-(trimethylsilyl)ethoxy]methoxy}-3,7,8,9-tetrahydro-6H-pyrrolo[ 2,3-c]-1,7-naphthyridin-6-one (1293388-54-1)

Guidance literature:

Multi-step reaction with 4 steps

1: toluene-4-sulfonic acid / tetrahydrofuran / 60 h

2: sodium cyanoborohydride; acetic acid / 2 h / 20 °C

3: N-iodo-succinimide / N,N-dimethyl-formamide / 1 h / 20 °C

4: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triethylamine / N,N-dimethyl-formamide

With bis-triphenylphosphine-palladium(II) chloride; N-iodo-succinimide; copper(l) iodide; sodium cyanoborohydride; toluene-4-sulfonic acid; acetic acid; triethylamine; In tetrahydrofuran; N,N-dimethyl-formamide; 4: Sonogashira coupling;

DOI:10.1021/jm200208d

upstream raw materials:

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

methyl 4-[(E)-2-butoxyvinyl]-1-(4-fluorobenzyl)-1H-pyrrolo[2,3-c]pyridine-5-carboxylate

methyl 1-(4-fluorobenzyl)-4-(2-((2-(trimethylsilyl)ethoxy)methoxyimino)ethyl)-1H-pyrrolo[2,3-c]pyridine-5-carboxylate

3-(4-fluorobenzyl)-7-((2-(trimethylsilyl)ethoxy)methoxy)-8,9-dihydro-3H-pyrrolo[2,3-c][1,7]naphthyridin-6(7H)-one

Downstream raw materials:

3-(4-fluorobenzyl)-1-(3-(N-methyl-acetamido)-propyl)-7-{[2-(trimethylsilyl)ethoxy]methoxy}-3,7,8,9-tetrahydro-6H-pyrrolo[2,3-c]-1,7-naphthyridin-6-one

3-(4-fluorobenzyl)-1-(3-(N-methyl-acetamido)-propyl)-7-hydroxy-3,7,8,9-tetrahydro-6H-pyrrolo[2,3-c]-1,7-naphthyridin-6-one hydrogen sulfate salt