N-(4-((6-bromo-1-methyl-1H-indazol-5-yl)oxy)-3-fluorophenyl)-1-(4-fluorophenyl)-6-methyl-2-oxo-1,2-dihydropyridine-3-carboxamide

Base Information

• Chemical Name: N-(4-((6-bromo-1-methyl-1H-indazol-5-yl)oxy)-3-fluorophenyl)-1-(4-fluorophenyl)-6-methyl-2-oxo-1,2-dihydropyridine-3-carboxamide
• CAS No.: 1577180-07-4
• Molecular Formula: C₂₇H₁₉BrF₂N₄O₃
• Molecular Weight: 565.374
• Mol file: 1577180-07-4.mol

Synonyms:N-(4-((6-bromo-1-methyl-1H-indazol-5-yl)oxy)-3-fluorophenyl)-1-(4-fluorophenyl)-6-methyl-2-oxo-1,2-dihydropyridine-3-carboxamide

Chemical Property of N-(4-((6-bromo-1-methyl-1H-indazol-5-yl)oxy)-3-fluorophenyl)-1-(4-fluorophenyl)-6-methyl-2-oxo-1,2-dihydropyridine-3-carboxamide

Chemical Property:

Purity/Quality:

95%+ ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-(4-((6-bromo-1-methyl-1H-indazol-5-yl)oxy)-3-fluorophenyl)-1-(4-fluorophenyl)-6-methyl-2-oxo-1,2-dihydropyridine-3-carboxamide

There total 23 articles about N-(4-((6-bromo-1-methyl-1H-indazol-5-yl)oxy)-3-fluorophenyl)-1-(4-fluorophenyl)-6-methyl-2-oxo-1,2-dihydropyridine-3-carboxamide 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:

1-(4-fluorophenyl)-6-methyl-2-oxo-1,2-dihydropyridine-3-carboxylic acid (888721-65-1) + C14H11BrFN3O → N-(4-((6-bromo-1-methyl-1H-indazol-5-yl)oxy)-3-fluorophenyl)-1-(4-fluorophenyl)-6-methyl-2-oxo-1,2-dihydropyridine-3-carboxamide (1577180-07-4)

Guidance literature:

With 4-methyl-morpholine; 2-chloro-4,6-dimethoxy-1 ,3,5-triazine; In acetonitrile; at 55 ℃; for 15h; Large scale;

DOI:10.1021/op400317z

Reference yield:

5-bromo-4-methoxy-2-methylbenzenamine (861084-04-0) → N-(4-((6-bromo-1-methyl-1H-indazol-5-yl)oxy)-3-fluorophenyl)-1-(4-fluorophenyl)-6-methyl-2-oxo-1,2-dihydropyridine-3-carboxamide (1577180-07-4)

Guidance literature:

Multi-step reaction with 6 steps

1.1: hydrogenchloride; sodium nitrite / water / 0.5 h / 0 °C / Large scale

1.2: 1 h / 0 - 5 °C / Large scale

1.3: 25 °C / Inert atmosphere; Large scale

2.1: potassium tert-butylate / tetrahydrofuran / 2.5 h / 20 - 25 °C / Large scale

3.1: aluminum (III) chloride / toluene / 5 h / 110 °C / Large scale

3.2: Large scale

4.1: sodium hydrogencarbonate / N,N-dimethyl-formamide / 15 h / 60 - 65 °C / Large scale

5.1: hydrogen; zinc dibromide / acetonitrile / 12 h / 55 °C / 760.05 Torr / Inert atmosphere

6.1: 4-methyl-morpholine; 2-chloro-4,6-dimethoxy-1 ,3,5-triazine / acetonitrile / 15 h / 55 °C / Large scale

With 4-methyl-morpholine; hydrogenchloride; aluminum (III) chloride; 2-chloro-4,6-dimethoxy-1 ,3,5-triazine; potassium tert-butylate; hydrogen; sodium hydrogencarbonate; zinc dibromide; sodium nitrite; In tetrahydrofuran; water; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1021/op400317z

Reference yield:

2-methyl-4-methoxyaniline (102-50-1) → N-(4-((6-bromo-1-methyl-1H-indazol-5-yl)oxy)-3-fluorophenyl)-1-(4-fluorophenyl)-6-methyl-2-oxo-1,2-dihydropyridine-3-carboxamide (1577180-07-4)

Guidance literature:

Multi-step reaction with 11 steps

1.1: dichloromethane / 3 h / 25 °C / Large scale

2.1: acetic acid; bromine / 10 h / 8 - 30 °C / Large scale

3.1: hydrogenchloride / methanol; water / Reflux; Large scale

4.1: hydrogenchloride; sodium nitrite / water / 0.5 h / 0 °C / Large scale

4.2: 1 h / 0 - 5 °C / Large scale

4.3: 25 °C / Inert atmosphere; Large scale

5.1: boron tribromide / dichloromethane

6.1: methanesulfonic acid / tetrahydrofuran

7.1: sodium hydrogencarbonate / N,N-dimethyl-formamide / 70 °C

8.1: methanesulfonic acid / methanol / 24 h / 50 °C

9.1: potassium carbonate / N,N-dimethyl-formamide / 24 h / 0 - 20 °C

10.1: hydrogen; zinc dibromide / acetonitrile / 12 h / 55 °C / 760.05 Torr / Inert atmosphere

11.1: 4-methyl-morpholine; 2-chloro-4,6-dimethoxy-1 ,3,5-triazine / acetonitrile / 15 h / 55 °C / Large scale

With 4-methyl-morpholine; hydrogenchloride; methanesulfonic acid; 2-chloro-4,6-dimethoxy-1 ,3,5-triazine; hydrogen; bromine; boron tribromide; sodium hydrogencarbonate; potassium carbonate; acetic acid; zinc dibromide; sodium nitrite; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/op400317z

upstream raw materials:

6-bromo-5-(2-fluoro-4-nitrophenoxy)-1H-indazole

1-(4-fluorophenyl)-6-methyl-2-oxo-1,2-dihydropyridine-3-carboxylic acid

1-(4-fluorophenyl)-6-methyl-3-cyano-2-oxo-1,2-dihydropyridine

3-((4-fluorophenyl)amino)-3-oxo-propionic acid ethyl ester

Downstream raw materials:

tert-butyl 4-(5-(2-fluoro-4-(1-(4-fluorophenyl)-6-methyl-2-oxo-1,2-dihydropyridine-3-carboxamido)phenoxy)-1-methyl-1H-indazol-6-yl)-1H-pyrazole-1-carboxylate

N-(3-fluoro-4-((1-methyl-6-(1H-pyrazol-4-yl)-1H-indazol-5-yl)oxy)phenyl)-1-(4-fluorophenyl)-6-methyl-2-oxo-1,2-dihydropyridine-3-carboxamide

3-fluoro-4-(1-methyl-6-(1H-pyrazol-4-yl)-1H-indazol-5-yloxy)aniline

Refernces