4-[3-(2-{3-cyano-4-[(1-methylethyl)oxy]phenyl}-5-pyrimidinyl)-5-fluoro-2-(methyloxy)phenyl]butanoic acid

Base Information

• Chemical Name: 4-[3-(2-{3-cyano-4-[(1-methylethyl)oxy]phenyl}-5-pyrimidinyl)-5-fluoro-2-(methyloxy)phenyl]butanoic acid
• CAS No.: 1334606-57-3
• Molecular Formula: C₂₅H₂₄FN₃O₄
• Molecular Weight: 449.482
• Mol file: 1334606-57-3.mol

Synonyms:4-[3-(2-{3-cyano-4-[(1-methylethyl)oxy]phenyl}-5-pyrimidinyl)-5-fluoro-2-(methyloxy)phenyl]butanoic acid

Chemical Property of 4-[3-(2-{3-cyano-4-[(1-methylethyl)oxy]phenyl}-5-pyrimidinyl)-5-fluoro-2-(methyloxy)phenyl]butanoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-[3-(2-{3-cyano-4-[(1-methylethyl)oxy]phenyl}-5-pyrimidinyl)-5-fluoro-2-(methyloxy)phenyl]butanoic acid

There total 10 articles about 4-[3-(2-{3-cyano-4-[(1-methylethyl)oxy]phenyl}-5-pyrimidinyl)-5-fluoro-2-(methyloxy)phenyl]butanoic acid 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-bromo-5-fluoro-2-(methyloxy)-3-nitrobenzene (179897-92-8) → 4-[3-(2-{3-cyano-4-[(1-methylethyl)oxy]phenyl}-5-pyrimidinyl)-5-fluoro-2-(methyloxy)phenyl]butanoic acid (1334606-57-3)

Guidance literature:

Multi-step reaction with 7 steps

1.1: caesium carbonate; tri-tert-butyl phosphine / tris-(dibenzylideneacetone)dipalladium⁽⁰⁾ / tetrahydrofuran / 20 °C / Inert atmosphere

2.1: ammonium chloride; iron / 90 °C

3.1: sodium nitrite; hydrogen bromide / acetonitrile; water / 0.17 h / 0 °C

3.2: 1 h / 50 °C

4.1: tricyclohexylphosphine; potassium acetate / tris-(dibenzylideneacetone)dipalladium⁽⁰⁾ / N,N-dimethyl-formamide / 0.75 h / 150 °C / Inert atmosphere; Sealed; Microwave irradiation

5.1: potassium phosphate / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,2-dimethoxyethane; water / 0.25 h / 120 °C / Inert atmosphere; Sealed; Microwave irradiation

6.1: potassium phosphate / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,2-dimethoxyethane; water / 0.25 h / 120 °C / Inert atmosphere; Sealed; Microwave irradiation

7.1: sodium hydroxide; water / isopropyl alcohol / 4 h / 20 °C

With potassium phosphate; tri-tert-butyl phosphine; water; hydrogen bromide; potassium acetate; iron; ammonium chloride; caesium carbonate; sodium hydroxide; sodium nitrite; tricyclohexylphosphine; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; 1,2-dimethoxyethane; water; N,N-dimethyl-formamide; isopropyl alcohol; acetonitrile;

Reference yield:

ethyl 4-[3-(2-{3-cyano-4-[(1-methylethyl)oxy]phenyl}-5-pyrimidinyl)-5-fluoro-2-(methyloxy)phenyl]butanoate (1334607-89-4) → 4-[3-(2-{3-cyano-4-[(1-methylethyl)oxy]phenyl}-5-pyrimidinyl)-5-fluoro-2-(methyloxy)phenyl]butanoic acid (1334606-57-3)

Guidance literature:

With water; sodium hydroxide; In isopropyl alcohol; at 20 ℃; for 4h;

Reference yield:

2-bromo-4-fluoro-1-methoxybenzene (452-08-4) → 4-[3-(2-{3-cyano-4-[(1-methylethyl)oxy]phenyl}-5-pyrimidinyl)-5-fluoro-2-(methyloxy)phenyl]butanoic acid (1334606-57-3)

Guidance literature:

Multi-step reaction with 8 steps

1.1: nitric acid; sulfuric acid / 0.5 h / -10 °C

2.1: caesium carbonate; tri-tert-butyl phosphine / tris-(dibenzylideneacetone)dipalladium⁽⁰⁾ / tetrahydrofuran / 20 °C / Inert atmosphere

3.1: ammonium chloride; iron / 90 °C

4.1: sodium nitrite; hydrogen bromide / acetonitrile; water / 0.17 h / 0 °C

4.2: 1 h / 50 °C

5.1: tricyclohexylphosphine; potassium acetate / tris-(dibenzylideneacetone)dipalladium⁽⁰⁾ / N,N-dimethyl-formamide / 0.75 h / 150 °C / Inert atmosphere; Sealed; Microwave irradiation

6.1: potassium phosphate / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,2-dimethoxyethane; water / 0.25 h / 120 °C / Inert atmosphere; Sealed; Microwave irradiation

7.1: potassium phosphate / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,2-dimethoxyethane; water / 0.25 h / 120 °C / Inert atmosphere; Sealed; Microwave irradiation

8.1: sodium hydroxide; water / isopropyl alcohol / 4 h / 20 °C

With potassium phosphate; tri-tert-butyl phosphine; sulfuric acid; water; hydrogen bromide; nitric acid; potassium acetate; iron; ammonium chloride; caesium carbonate; sodium hydroxide; sodium nitrite; tricyclohexylphosphine; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; 1,2-dimethoxyethane; water; N,N-dimethyl-formamide; isopropyl alcohol; acetonitrile;

upstream raw materials:

2-bromo-4-fluoro-1-methoxybenzene

5-bromo-2-hydroxybenzonitrile

1-bromo-5-fluoro-2-(methyloxy)-3-nitrobenzene

5-bromo-2-[(1-methylethyl)oxy]benzonitrile