methyl 4-{2,5-difluoro-3-[4-(2-methyl-1H-imidazol-1-yl)]benzyloxyphenyl}-3,4,5,6-tetrahydro-2H-pyran-4-carboxylate

Base Information

• Chemical Name: methyl 4-{2,5-difluoro-3-[4-(2-methyl-1H-imidazol-1-yl)]benzyloxyphenyl}-3,4,5,6-tetrahydro-2H-pyran-4-carboxylate
• CAS No.: 179420-61-2
• Molecular Formula: C₂₄H₂₄F₂N₂O₄
• Molecular Weight: 442.462
• Mol file: 179420-61-2.mol

Synonyms:methyl 4-{2,5-difluoro-3-[4-(2-methyl-1H-imidazol-1-yl)]benzyloxyphenyl}-3,4,5,6-tetrahydro-2H-pyran-4-carboxylate

Chemical Property of methyl 4-{2,5-difluoro-3-[4-(2-methyl-1H-imidazol-1-yl)]benzyloxyphenyl}-3,4,5,6-tetrahydro-2H-pyran-4-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 4-{2,5-difluoro-3-[4-(2-methyl-1H-imidazol-1-yl)]benzyloxyphenyl}-3,4,5,6-tetrahydro-2H-pyran-4-carboxylate

There total 11 articles about methyl 4-{2,5-difluoro-3-[4-(2-methyl-1H-imidazol-1-yl)]benzyloxyphenyl}-3,4,5,6-tetrahydro-2H-pyran-4-carboxylate 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: 49.0%

methyl 4-(2,5-difluoro-3-hydroxyphenyl)-3,4,5,6-tetrahydro-2H-pyran-4-carboxylate (179421-06-8) + 4-(2-methyl-1H-imidazol-1-yl)benzyl chloride hydrochloride → methyl 4-{2,5-difluoro-3-[4-(2-methyl-1H-imidazol-1-yl)]benzyloxyphenyl}-3,4,5,6-tetrahydro-2H-pyran-4-carboxylate (179420-61-2)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide;

DOI:10.1248/cpb.53.965

Reference yield:

2,5-difluoro-3-methoxybenzaldehyde (179421-01-3) → methyl 4-{2,5-difluoro-3-[4-(2-methyl-1H-imidazol-1-yl)]benzyloxyphenyl}-3,4,5,6-tetrahydro-2H-pyran-4-carboxylate (179420-61-2)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 95 percent / NaBH₄ / ethanol / 0.5 h / 20 °C

2.1: Et₃N / CH₂Cl₂ / 3.5 h / 20 °C

3.1: 5.91 g / dimethylsulfoxide / 2 h

4.1: KOH / ethane-1,2-diol / 1 h / 120 °C

5.1: 3.80 g / H₂SO₄ / 1 h / Heating

6.1: NaH; 15-crown-5 / dimethylformamide / 0.67 h / 20 °C

6.2: NaI / dimethylformamide / 10.5 h

7.1: BBr₃ / CH₂Cl₂ / 23 h

8.1: 49 percent / K₂CO₃ / dimethylformamide

With potassium hydroxide; sodium tetrahydroborate; 15-crown-5; sulfuric acid; boron tribromide; sodium hydride; potassium carbonate; triethylamine; In ethanol; dichloromethane; ethylene glycol; dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1248/cpb.53.965

Reference yield:

2,5-difluoro-3-methoxybenzyl alcohol (179421-02-4) → methyl 4-{2,5-difluoro-3-[4-(2-methyl-1H-imidazol-1-yl)]benzyloxyphenyl}-3,4,5,6-tetrahydro-2H-pyran-4-carboxylate (179420-61-2)

Guidance literature:

Multi-step reaction with 7 steps

1.1: Et₃N / CH₂Cl₂ / 3.5 h / 20 °C

2.1: 5.91 g / dimethylsulfoxide / 2 h

3.1: KOH / ethane-1,2-diol / 1 h / 120 °C

4.1: 3.80 g / H₂SO₄ / 1 h / Heating

5.1: NaH; 15-crown-5 / dimethylformamide / 0.67 h / 20 °C

5.2: NaI / dimethylformamide / 10.5 h

6.1: BBr₃ / CH₂Cl₂ / 23 h

7.1: 49 percent / K₂CO₃ / dimethylformamide

With potassium hydroxide; 15-crown-5; sulfuric acid; boron tribromide; sodium hydride; potassium carbonate; triethylamine; In dichloromethane; ethylene glycol; dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1248/cpb.53.965

upstream raw materials:

methyl 4-(2,5-difluoro-3-hydroxyphenyl)-3,4,5,6-tetrahydro-2H-pyran-4-carboxylate

2,5-difluoro-3-methoxybenzaldehyde

2,5-difluoro-3-methoxybenzyl alcohol

2,5-difluoro-3-methoxyphenylacetonitrile