(1R,2R)-N-[cis-2-(6-fluoro-2-methoxy-3-propionylphenyl)cyclopropyl]-N'-[2-(5-bromopyridyl)]urea

Base Information

• Chemical Name: (1R,2R)-N-[cis-2-(6-fluoro-2-methoxy-3-propionylphenyl)cyclopropyl]-N'-[2-(5-bromopyridyl)]urea
• CAS No.: 247230-98-4
• Molecular Formula: C₁₉H₁₉BrFN₃O₃
• Molecular Weight: 436.281

Synonyms:(1R,2R)-N-[cis-2-(6-fluoro-2-methoxy-3-propionylphenyl)cyclopropyl]-N'-[2-(5-bromopyridyl)]urea

Chemical Property of (1R,2R)-N-[cis-2-(6-fluoro-2-methoxy-3-propionylphenyl)cyclopropyl]-N'-[2-(5-bromopyridyl)]urea

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

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Technology Process of (1R,2R)-N-[cis-2-(6-fluoro-2-methoxy-3-propionylphenyl)cyclopropyl]-N'-[2-(5-bromopyridyl)]urea

There total 12 articles about (1R,2R)-N-[cis-2-(6-fluoro-2-methoxy-3-propionylphenyl)cyclopropyl]-N'-[2-(5-bromopyridyl)]urea 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:

3-fluorophenol (372-20-3) → (1R,2R)-N-[cis-2-(6-fluoro-2-methoxy-3-propionylphenyl)cyclopropyl]-N'-[2-(5-bromopyridyl)]urea (247230-98-4)

Guidance literature:

Multi-step reaction with 12 steps

1.1: 100 percent / pyridine / CH₂Cl₂ / 0.5 h / 20 °C

2.1: 88 percent / AlCl₃ / 0.17 h / 150 °C

3.1: 97 percent / K₂CO₃ / acetone / 12 h / 40 °C

4.1: 86 percent / p-TsOH / benzene / 12 h / Heating

5.1: n-BuLi / hexane; tetrahydrofuran / -65 - -40 °C

5.2: 25 percent / hexane; tetrahydrofuran / 0.5 h / -65 - 20 °C

6.1: n-BuLi / hexane; tetrahydrofuran / 20 °C

6.2: 70 percent / hexane; tetrahydrofuran / 2 h / 20 °C

7.1: 45 percent / 2,2'-isopropylidenebis[(4S)-4-tert-butyl-2-oxazoline]; Cu(I)OTf / CHCl₃ / 2 h / 20 °C

8.1: 97 percent / 6 M aq. HCl / dioxane / 1.5 h / 20 °C

9.1: 92 percent / aq. LiOH / dioxane / 2.5 h / 80 °C

10.1: diphenylphosphorazidate; Et₃N / toluene / 0.5 h / 20 °C

11.1: toluene / 0.25 h / 120 °C

12.1: toluene / 3 h / Heating

With pyridine; hydrogenchloride; lithium hydroxide; n-butyllithium; aluminium trichloride; diphenyl phosphoryl azide; copper(I) triflate; potassium carbonate; 2,2'-isopropylidenebis[(4S)-4-tert-butyl-2-oxazoline]; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; 1,4-dioxane; hexane; dichloromethane; chloroform; acetone; toluene; benzene; 1.1: Acylation / 2.1: Fries rearrangement / 3.1: Methylation / 4.1: ketalization / 5.1: Metallation / 5.2: Formylation / 6.1: Metallation / 6.2: Condensation / 7.1: asymmetric cyclopropanation / 8.1: deketalization / 9.1: Hydrolysis / 10.1: Substitution / 11.1: Curtius rearrangement / 12.1: Addition;

DOI:10.1021/jm990095j

Reference yield:

3-fluoro-1-propionyloxybenzene (92310-73-1) → (1R,2R)-N-[cis-2-(6-fluoro-2-methoxy-3-propionylphenyl)cyclopropyl]-N'-[2-(5-bromopyridyl)]urea (247230-98-4)

Guidance literature:

Multi-step reaction with 11 steps

1.1: 88 percent / AlCl₃ / 0.17 h / 150 °C

2.1: 97 percent / K₂CO₃ / acetone / 12 h / 40 °C

3.1: 86 percent / p-TsOH / benzene / 12 h / Heating

4.1: n-BuLi / hexane; tetrahydrofuran / -65 - -40 °C

4.2: 25 percent / hexane; tetrahydrofuran / 0.5 h / -65 - 20 °C

5.1: n-BuLi / hexane; tetrahydrofuran / 20 °C

5.2: 70 percent / hexane; tetrahydrofuran / 2 h / 20 °C

6.1: 45 percent / 2,2'-isopropylidenebis[(4S)-4-tert-butyl-2-oxazoline]; Cu(I)OTf / CHCl₃ / 2 h / 20 °C

7.1: 97 percent / 6 M aq. HCl / dioxane / 1.5 h / 20 °C

8.1: 92 percent / aq. LiOH / dioxane / 2.5 h / 80 °C

9.1: diphenylphosphorazidate; Et₃N / toluene / 0.5 h / 20 °C

10.1: toluene / 0.25 h / 120 °C

11.1: toluene / 3 h / Heating

With hydrogenchloride; lithium hydroxide; n-butyllithium; aluminium trichloride; diphenyl phosphoryl azide; copper(I) triflate; potassium carbonate; 2,2'-isopropylidenebis[(4S)-4-tert-butyl-2-oxazoline]; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; 1,4-dioxane; hexane; chloroform; acetone; toluene; benzene; 1.1: Fries rearrangement / 2.1: Methylation / 3.1: ketalization / 4.1: Metallation / 4.2: Formylation / 5.1: Metallation / 5.2: Condensation / 6.1: asymmetric cyclopropanation / 7.1: deketalization / 8.1: Hydrolysis / 9.1: Substitution / 10.1: Curtius rearrangement / 11.1: Addition;

DOI:10.1021/jm990095j

Reference yield:

1-(4-fluoro-2-hydroxyphenyl)propan-1-one (247230-94-0) → (1R,2R)-N-[cis-2-(6-fluoro-2-methoxy-3-propionylphenyl)cyclopropyl]-N'-[2-(5-bromopyridyl)]urea (247230-98-4)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 97 percent / K₂CO₃ / acetone / 12 h / 40 °C

2.1: 86 percent / p-TsOH / benzene / 12 h / Heating

3.1: n-BuLi / hexane; tetrahydrofuran / -65 - -40 °C

3.2: 25 percent / hexane; tetrahydrofuran / 0.5 h / -65 - 20 °C

4.1: n-BuLi / hexane; tetrahydrofuran / 20 °C

4.2: 70 percent / hexane; tetrahydrofuran / 2 h / 20 °C

5.1: 45 percent / 2,2'-isopropylidenebis[(4S)-4-tert-butyl-2-oxazoline]; Cu(I)OTf / CHCl₃ / 2 h / 20 °C

6.1: 97 percent / 6 M aq. HCl / dioxane / 1.5 h / 20 °C

7.1: 92 percent / aq. LiOH / dioxane / 2.5 h / 80 °C

8.1: diphenylphosphorazidate; Et₃N / toluene / 0.5 h / 20 °C

9.1: toluene / 0.25 h / 120 °C

10.1: toluene / 3 h / Heating

With hydrogenchloride; lithium hydroxide; n-butyllithium; diphenyl phosphoryl azide; copper(I) triflate; potassium carbonate; 2,2'-isopropylidenebis[(4S)-4-tert-butyl-2-oxazoline]; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; 1,4-dioxane; hexane; chloroform; acetone; toluene; benzene; 1.1: Methylation / 2.1: ketalization / 3.1: Metallation / 3.2: Formylation / 4.1: Metallation / 4.2: Condensation / 5.1: asymmetric cyclopropanation / 6.1: deketalization / 7.1: Hydrolysis / 8.1: Substitution / 9.1: Curtius rearrangement / 10.1: Addition;

DOI:10.1021/jm990095j

upstream raw materials:

5-bromo-2-pyridylamine

3-fluorophenol

3-fluoro-1-propionyloxybenzene

1-(4-fluoro-2-hydroxyphenyl)propan-1-one

Downstream raw materials:

(1R,2R)-N-[cis-2-(6-fluoro-2-hydroxy-3-propionylphenyl)cyclopropyl]-N'-[2-(5-bromopyridyl)]urea

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