tert-butyl 3-(3-(4-fluorobenzyl)-6-oxo-7-((2-(trimethylsilyl)ethoxy)methoxy)-6,7,8,9-tetrahydro-3H-pyrrolo[2,3-c][1,7]naphthyridin-1-yl)propanoate

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Chemical Name:tert-butyl 3-(3-(4-fluorobenzyl)-6-oxo-7-((2-(trimethylsilyl)ethoxy)methoxy)-6,7,8,9-tetrahydro-3H-pyrrolo[2,3-c][1,7]naphthyridin-1-yl)propanoate
CAS No.:1293387-96-8
Molecular Formula:C₃₀H₄₀FN₃O₅Si
Molecular Weight:569.749
Hs Code.:

Synonyms:tert-butyl 3-(3-(4-fluorobenzyl)-6-oxo-7-((2-(trimethylsilyl)ethoxy)methoxy)-6,7,8,9-tetrahydro-3H-pyrrolo[2,3-c][1,7]naphthyridin-1-yl)propanoate

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Chemical Property of tert-butyl 3-(3-(4-fluorobenzyl)-6-oxo-7-((2-(trimethylsilyl)ethoxy)methoxy)-6,7,8,9-tetrahydro-3H-pyrrolo[2,3-c][1,7]naphthyridin-1-yl)propanoate

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Technology Process of tert-butyl 3-(3-(4-fluorobenzyl)-6-oxo-7-((2-(trimethylsilyl)ethoxy)methoxy)-6,7,8,9-tetrahydro-3H-pyrrolo[2,3-c][1,7]naphthyridin-1-yl)propanoate

There total 17 articles about tert-butyl 3-(3-(4-fluorobenzyl)-6-oxo-7-((2-(trimethylsilyl)ethoxy)methoxy)-6,7,8,9-tetrahydro-3H-pyrrolo[2,3-c][1,7]naphthyridin-1-yl)propanoate 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: 87.0%

: 1293387-95-7
(E)-tert-butyl 3-(3-(4-fluorobenzyl)-6-oxo-7-((2-(trimethylsilyl)ethoxy)methoxy)-6,7,8,9-tetrahydro-3H-pyrrolo[2,3-c][1,7]naphthyridin-1-yl)acrylate

: 1293387-96-8
tert-butyl 3-(3-(4-fluorobenzyl)-6-oxo-7-((2-(trimethylsilyl)ethoxy)methoxy)-6,7,8,9-tetrahydro-3H-pyrrolo[2,3-c][1,7]naphthyridin-1-yl)propanoate

Guidance literature:: With hydrogen; palladium(II) hydroxide; In methanol; for 2h; under 760.051 Torr;
DOI:10.1021/jm200208d

Reference yield:

: 936-12-9
2-methyl-1H-pyrrole-3-carboxylic acid ethyl ester

: 1293387-96-8
tert-butyl 3-(3-(4-fluorobenzyl)-6-oxo-7-((2-(trimethylsilyl)ethoxy)methoxy)-6,7,8,9-tetrahydro-3H-pyrrolo[2,3-c][1,7]naphthyridin-1-yl)propanoate

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: 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: palladium diacetate; triethylamine; tris-(o-tolyl)phosphine / N,N-dimethyl-formamide / 3 h / 80 °C / Inert atmosphere

12.1: hydrogen; palladium(II) hydroxide / methanol / 2 h / 760.05 Torr

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; N-Bromosuccinimide; N-iodo-succinimide; N-Methyldicyclohexylamine; palladium 10% on activated carbon; potassium tert-butylate; hydrogen; palladium diacetate; palladium(II) hydroxide; sodium cyanoborohydride; toluene-4-sulfonic acid; acetic acid; triethylamine; tris-(o-tolyl)phosphine; lithium chloride; lithium hexamethyldisilazane; tri tert-butylphosphoniumtetrafluoroborate; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; 11.1: Heck reaction;
DOI:10.1021/jm200208d

Reference yield:

: 934621-80-4
methyl 4-[(E)-2-butoxyvinyl]-1-(4-fluorobenzyl)-1H-pyrrolo[2,3-c]pyridine-5-carboxylate

: 1293387-96-8
tert-butyl 3-(3-(4-fluorobenzyl)-6-oxo-7-((2-(trimethylsilyl)ethoxy)methoxy)-6,7,8,9-tetrahydro-3H-pyrrolo[2,3-c][1,7]naphthyridin-1-yl)propanoate

Guidance literature:: Multi-step reaction with 5 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: palladium diacetate; triethylamine; tris-(o-tolyl)phosphine / N,N-dimethyl-formamide / 3 h / 80 °C / Inert atmosphere

5: hydrogen; palladium(II) hydroxide / methanol / 2 h / 760.05 Torr

With N-iodo-succinimide; hydrogen; palladium diacetate; palladium(II) hydroxide; sodium cyanoborohydride; toluene-4-sulfonic acid; acetic acid; triethylamine; tris-(o-tolyl)phosphine; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; 4: Heck reaction;
DOI:10.1021/jm200208d