3-(2,6-difluorophenyl)-1-ethyl-7-((5-fluoropyridin-2-yl)amino)-1,6-naphthyridin-2(1H)-one

Base Information

• Chemical Name: 3-(2,6-difluorophenyl)-1-ethyl-7-((5-fluoropyridin-2-yl)amino)-1,6-naphthyridin-2(1H)-one
• CAS No.: 1588422-60-9
• Molecular Formula: C₂₁H₁₅F₃N₄O
• Molecular Weight: 396.372
• Mol file: 1588422-60-9.mol

Synonyms:3-(2,6-difluorophenyl)-1-ethyl-7-((5-fluoropyridin-2-yl)amino)-1,6-naphthyridin-2(1H)-one

Chemical Property of 3-(2,6-difluorophenyl)-1-ethyl-7-((5-fluoropyridin-2-yl)amino)-1,6-naphthyridin-2(1H)-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-(2,6-difluorophenyl)-1-ethyl-7-((5-fluoropyridin-2-yl)amino)-1,6-naphthyridin-2(1H)-one

There total 10 articles about 3-(2,6-difluorophenyl)-1-ethyl-7-((5-fluoropyridin-2-yl)amino)-1,6-naphthyridin-2(1H)-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: 4.93%

2-(2,6-difluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (863868-37-5) + 1-ethyl-7-(5-methylpyridin-2-ylamino)-1H-[1,6]naphthyridin-2-one (1588423-52-2) → 3-(2,6-difluorophenyl)-1-ethyl-7-((5-fluoropyridin-2-yl)amino)-1,6-naphthyridin-2(1H)-one (1588422-60-9)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate; In 1,4-dioxane; water; at 60 ℃; for 3h; Inert atmosphere; Microwave irradiation; Sealed tube;

Reference yield:

ethyl 4,6-dichloronicotinate (40296-46-6) → 3-(2,6-difluorophenyl)-1-ethyl-7-((5-fluoropyridin-2-yl)amino)-1,6-naphthyridin-2(1H)-one (1588422-60-9)

Guidance literature:

Multi-step reaction with 7 steps

1.1: tetrahydrofuran / 16.5 h / 0 - 20 °C

2.1: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / -78 °C

3.1: Dess-Martin periodane / tetrahydrofuran / 5 h / 0 - 20 °C

4.1: lithium diisopropyl amide / tetrahydrofuran / 0.5 h / -78 °C

4.2: 16 h / 20 °C

5.1: sodium t-butanolate; XPhos; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾ / 1,4-dioxane / 16 h / 100 °C / Inert atmosphere

6.1: trifluoroacetic acid / acetic acid / 0.5 h / 20 - 70 °C

6.2: 16 h / 70 °C / Inert atmosphere

7.1: bis-triphenylphosphine-palladium(II) chloride; sodium carbonate / water; 1,4-dioxane / 3 h / 60 °C / Inert atmosphere; Microwave irradiation; Sealed tube

With bis-triphenylphosphine-palladium(II) chloride; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; lithium aluminium tetrahydride; sodium carbonate; Dess-Martin periodane; trifluoroacetic acid; sodium t-butanolate; lithium diisopropyl amide; XPhos; In tetrahydrofuran; 1,4-dioxane; water; acetic acid;

Reference yield:

6-chloro-4-ethylamino-nicotinic acid ethyl ester (959162-97-1) → 3-(2,6-difluorophenyl)-1-ethyl-7-((5-fluoropyridin-2-yl)amino)-1,6-naphthyridin-2(1H)-one (1588422-60-9)

Guidance literature:

Multi-step reaction with 6 steps

1.1: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / -78 °C

2.1: Dess-Martin periodane / tetrahydrofuran / 5 h / 0 - 20 °C

3.1: lithium diisopropyl amide / tetrahydrofuran / 0.5 h / -78 °C

3.2: 16 h / 20 °C

4.1: sodium t-butanolate; XPhos; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾ / 1,4-dioxane / 16 h / 100 °C / Inert atmosphere

5.1: trifluoroacetic acid / acetic acid / 0.5 h / 20 - 70 °C

5.2: 16 h / 70 °C / Inert atmosphere

6.1: bis-triphenylphosphine-palladium(II) chloride; sodium carbonate / water; 1,4-dioxane / 3 h / 60 °C / Inert atmosphere; Microwave irradiation; Sealed tube

With bis-triphenylphosphine-palladium(II) chloride; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; lithium aluminium tetrahydride; sodium carbonate; Dess-Martin periodane; trifluoroacetic acid; sodium t-butanolate; lithium diisopropyl amide; XPhos; In tetrahydrofuran; 1,4-dioxane; water; acetic acid;

upstream raw materials:

ethyl 4,6-dichloronicotinate

6-chloro-4-ethylamino-nicotinic acid ethyl ester

(6-chloro-4-(ethylamino)pyridin-3-yl)methanol

6-chloro-4-ethylamino-pyridine-3-carbaldehyde