3-cyclohexyl-1-dimethylcarbamoylmethyl-2-furan-3-yl-1H-indole-6-carboxylic acid methyl ester

Base Information

• Chemical Name: 3-cyclohexyl-1-dimethylcarbamoylmethyl-2-furan-3-yl-1H-indole-6-carboxylic acid methyl ester
• CAS No.: 948553-66-0
• Molecular Formula: C₂₄H₂₈N₂O₄
• Molecular Weight: 408.497

Synonyms:3-cyclohexyl-1-dimethylcarbamoylmethyl-2-furan-3-yl-1H-indole-6-carboxylic acid methyl ester

Chemical Property of 3-cyclohexyl-1-dimethylcarbamoylmethyl-2-furan-3-yl-1H-indole-6-carboxylic acid methyl ester

Chemical Property:

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Technology Process of 3-cyclohexyl-1-dimethylcarbamoylmethyl-2-furan-3-yl-1H-indole-6-carboxylic acid methyl ester

There total 5 articles about 3-cyclohexyl-1-dimethylcarbamoylmethyl-2-furan-3-yl-1H-indole-6-carboxylic acid methyl ester 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:

methyl 2-bromo-3-cyclohexyl-1-[2-(dimethylamino)-2-oxoethyl]-1H-indole-6-carboxylate (735287-01-1) + furan-3-boronic acid (55552-70-0) → 3-cyclohexyl-1-dimethylcarbamoylmethyl-2-furan-3-yl-1H-indole-6-carboxylic acid methyl ester (948553-66-0)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate; In 1,2-dimethoxyethane; ethanol; at 80 ℃; for 6h;

DOI:10.1021/jm050056+

Reference yield:

methyl 2-bromo-3-cyclohexyl-1H-indole-6-carboxylate (494799-19-8) → 3-cyclohexyl-1-dimethylcarbamoylmethyl-2-furan-3-yl-1H-indole-6-carboxylic acid methyl ester (948553-66-0)

Guidance literature:

Multi-step reaction with 4 steps

1: aq. Na₂CO₃ / Pd(PPh₃)2Cl₂ / dioxane / Heating

2: 95 percent / NaH / dimethylformamide / 60 °C

3: 100 percent / CF₃CO₂H / CH₂Cl₂ / 2 h

4: TBTU; i-Pr₂NEt / CH₂Cl₂ / 16 h

With sodium hydride; sodium carbonate; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; bis-triphenylphosphine-palladium(II) chloride; In 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide; 1: Suzuki coupling;

DOI:10.1016/j.bmcl.2007.06.093

Reference yield:

[3-cyclohexyl-2-(3-furyl)-6-(methoxycarbonyl)-1H-indol-1-yl]acetic acid (494799-84-7) + dimethyl amine (124-40-3) → 3-cyclohexyl-1-dimethylcarbamoylmethyl-2-furan-3-yl-1H-indole-6-carboxylic acid methyl ester (948553-66-0)

Guidance literature:

With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In dichloromethane; for 16h;

DOI:10.1016/j.bmcl.2007.06.093

upstream raw materials:

methyl 2-bromo-3-cyclohexyl-1-[2-(dimethylamino)-2-oxoethyl]-1H-indole-6-carboxylate

furan-3-boronic acid

[3-cyclohexyl-2-(3-furyl)-6-(methoxycarbonyl)-1H-indol-1-yl]acetic acid

dimethyl amine

Downstream raw materials:

3-cyclohexyl-1-[2-(dimethylamino)-2-oxoethyl]-2-(3-furyl)-1H-indole-6-carboxylic acid

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