ethyl ((1S)-5-{3-[4-(6-methyl-2-pyridinyl)phenoxy]propoxy}-2,3-dihydro-1H-inden-1-yl)acetate

Base Information

• Chemical Name: ethyl ((1S)-5-{3-[4-(6-methyl-2-pyridinyl)phenoxy]propoxy}-2,3-dihydro-1H-inden-1-yl)acetate
• CAS No.: 724466-79-9
• Molecular Formula: C₂₈H₃₁NO₄
• Molecular Weight: 445.558

Synonyms:ethyl ((1S)-5-{3-[4-(6-methyl-2-pyridinyl)phenoxy]propoxy}-2,3-dihydro-1H-inden-1-yl)acetate

Chemical Property of ethyl ((1S)-5-{3-[4-(6-methyl-2-pyridinyl)phenoxy]propoxy}-2,3-dihydro-1H-inden-1-yl)acetate

Chemical Property:

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Technology Process of ethyl ((1S)-5-{3-[4-(6-methyl-2-pyridinyl)phenoxy]propoxy}-2,3-dihydro-1H-inden-1-yl)acetate

There total 8 articles about ethyl ((1S)-5-{3-[4-(6-methyl-2-pyridinyl)phenoxy]propoxy}-2,3-dihydro-1H-inden-1-yl)acetate 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: 40.0%

ethyl {(1S)-5-[3-(4-iodophenoxy)propoxy]-2,3-dihydro-1H-inden-1-yl}acetate (724466-73-3) + 2-bromo-6-methylpyridine (5315-25-3) → ethyl ((1S)-5-{3-[4-(6-methyl-2-pyridinyl)phenoxy]propoxy}-2,3-dihydro-1H-inden-1-yl)acetate (724466-79-9)

Guidance literature:

ethyl {(1S)-5-[3-(4-iodophenoxy)propoxy]-2,3-dihydro-1H-inden-1-yl}acetate; With potassium acetate; bis(pinacol)diborane; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; In N,N-dimethyl-formamide; at 80 ℃; for 2h;

2-bromo-6-methylpyridine; With sodium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; In N,N-dimethyl-formamide; at 80 ℃; for 12h;

DOI:10.1021/jm061299k

Reference yield:

[(1S)-5-methoxy-2,3-dihydro-1H-inden-1-yl]acetic acid (496061-78-0) → ethyl ((1S)-5-{3-[4-(6-methyl-2-pyridinyl)phenoxy]propoxy}-2,3-dihydro-1H-inden-1-yl)acetate (724466-79-9)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 100 percent / chlorotrimethylsilane / 12 h / 20 °C

2.1: 96 percent / AlCl₃; EtSH / CH₂Cl₂ / 2.5 h / 10 °C

3.1: Cs₂CO₃ / dimethylformamide / 14 h / 20 - 80 °C

4.1: 22 percent / Cs₂CO₃ / dimethylformamide / 16 h / 20 °C

5.1: bis(pinacolato)diboron; KOAc / PdCl₂(dppf)*CH₂Cl₂ / dimethylformamide / 2 h / 80 °C

5.2: 40 percent / aq. Na₂CO₃ / PdCl₂(dppf)*CH₂Cl₂ / dimethylformamide / 12 h / 80 °C

With chloro-trimethyl-silane; aluminium trichloride; potassium acetate; caesium carbonate; bis(pinacol)diborane; ethanethiol; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm061299k

Reference yield:

ethyl [(1S)-5-methoxy-2,3-dihydro-1H-inden-1-yl]acetate (496061-79-1) → ethyl ((1S)-5-{3-[4-(6-methyl-2-pyridinyl)phenoxy]propoxy}-2,3-dihydro-1H-inden-1-yl)acetate (724466-79-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 96 percent / AlCl₃; EtSH / CH₂Cl₂ / 2.5 h / 10 °C

2.1: Cs₂CO₃ / dimethylformamide / 14 h / 20 - 80 °C

3.1: 22 percent / Cs₂CO₃ / dimethylformamide / 16 h / 20 °C

4.1: bis(pinacolato)diboron; KOAc / PdCl₂(dppf)*CH₂Cl₂ / dimethylformamide / 2 h / 80 °C

4.2: 40 percent / aq. Na₂CO₃ / PdCl₂(dppf)*CH₂Cl₂ / dimethylformamide / 12 h / 80 °C

With aluminium trichloride; potassium acetate; caesium carbonate; bis(pinacol)diborane; ethanethiol; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm061299k

upstream raw materials:

ethyl {(1S)-5-[3-(4-iodophenoxy)propoxy]-2,3-dihydro-1H-inden-1-yl}acetate

2-bromo-6-methylpyridine

[(1S)-5-methoxy-2,3-dihydro-1H-inden-1-yl]acetic acid

ethyl [(1S)-5-methoxy-2,3-dihydro-1H-inden-1-yl]acetate

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