3-fluoro-4-[2-phenyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridin-4-yloxy]-phenyl-carbamic acid t-butyl ester

Base Information

• Chemical Name: 3-fluoro-4-[2-phenyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridin-4-yloxy]-phenyl-carbamic acid t-butyl ester
• CAS No.: 1221714-49-3
• Molecular Formula: C₃₀H₃₆FN₃O₄Si
• Molecular Weight: 549.717
• Mol file: 1221714-49-3.mol

Synonyms:3-fluoro-4-[2-phenyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridin-4-yloxy]-phenyl-carbamic acid t-butyl ester

Chemical Property of 3-fluoro-4-[2-phenyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridin-4-yloxy]-phenyl-carbamic acid t-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-fluoro-4-[2-phenyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridin-4-yloxy]-phenyl-carbamic acid t-butyl ester

There total 5 articles about 3-fluoro-4-[2-phenyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridin-4-yloxy]-phenyl-carbamic acid t-butyl ester 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: 84.0%

N-(3-fluoro-4-hydroxyphenyl)carbamic acid tert-butyl ester (859537-27-2) + 4-chloro-2-phenyl-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridine (1221714-48-2) → 3-fluoro-4-[2-phenyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridin-4-yloxy]-phenyl-carbamic acid t-butyl ester (1221714-49-3)

Guidance literature:

With potassium carbonate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; XPhos; In toluene; at 110 ℃; Inert atmosphere;

Reference yield:

4-chloro-7-azaindole (55052-28-3) → 3-fluoro-4-[2-phenyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridin-4-yloxy]-phenyl-carbamic acid t-butyl ester (1221714-49-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: sodium hydride / tetrahydrofuran / 0 °C / Inert atmosphere

1.2: 3 h / 80 °C / Inert atmosphere

2.1: n-butyllithium / hexane; tetrahydrofuran / -78 °C / Inert atmosphere

2.2: 20 °C

3.1: potassium carbonate / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,4-dioxane / 2 h / 80 °C

4.1: potassium carbonate / tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; XPhos / toluene / 110 °C / Inert atmosphere

With n-butyllithium; sodium hydride; potassium carbonate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tetrakis(triphenylphosphine) palladium⁽⁰⁾; XPhos; In tetrahydrofuran; 1,4-dioxane; hexane; toluene;

Reference yield:

4-chloro-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridine (869335-19-3) → 3-fluoro-4-[2-phenyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridin-4-yloxy]-phenyl-carbamic acid t-butyl ester (1221714-49-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: n-butyllithium / hexane; tetrahydrofuran / -78 °C / Inert atmosphere

1.2: 20 °C

2.1: potassium carbonate / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,4-dioxane / 2 h / 80 °C

3.1: potassium carbonate / tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; XPhos / toluene / 110 °C / Inert atmosphere

With n-butyllithium; potassium carbonate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tetrakis(triphenylphosphine) palladium⁽⁰⁾; XPhos; In tetrahydrofuran; 1,4-dioxane; hexane; toluene;

upstream raw materials:

4-chloro-7-azaindole

4-chloro-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridine

4-chloro-2-iodo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridine

(2-trimethylethylsilylethoxy)methyl chloride

Downstream raw materials:

3-fluoro-4-(2-phenyl-1H-pyrrolo[2,3-b]pyridin-4-yloxy)-phenylamine

1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxylic acid [3-fluoro-4-(2-phenyl-1H-pyrrolo[2,3-b]pyridin-4-yloxy)-phenyl]-amide