methyl α-<1-tosylindol-3-acetic(trans-3,4-dibromo-3-ethylpiperidine)amide-2-yl>acrylate

Base Information

• Chemical Name: methyl α-<1-tosylindol-3-acetic(trans-3,4-dibromo-3-ethylpiperidine)amide-2-yl>acrylate
• CAS No.: 88839-90-1
• Molecular Formula: C₂₈H₃₀Br₂N₂O₅S
• Molecular Weight: 666.431

Synonyms:methyl α-<1-tosylindol-3-acetic(trans-3,4-dibromo-3-ethylpiperidine)amide-2-yl>acrylate

Chemical Property of methyl α-<1-tosylindol-3-acetic(trans-3,4-dibromo-3-ethylpiperidine)amide-2-yl>acrylate

Chemical Property:

Purity/Quality:

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Technology Process of methyl α-<1-tosylindol-3-acetic(trans-3,4-dibromo-3-ethylpiperidine)amide-2-yl>acrylate

There total 10 articles about methyl α-<1-tosylindol-3-acetic(trans-3,4-dibromo-3-ethylpiperidine)amide-2-yl>acrylate 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: 93.0%

methyl α-<1-tosylindol-3-acetic(1,2,5,6-tetrahydro-3-ethylpyridine)amide-2yl>acrylate (77130-12-2) → methyl α-<1-tosylindol-3-acetic(trans-3,4-dibromo-3-ethylpiperidine)amide-2-yl>acrylate (88839-90-1)

Guidance literature:

With bromine; In dichloromethane; at -78 ℃; for 0.0833333h;

DOI:10.1016/S0040-4020(01)88613-0

Reference yield:

3-ethylpyridine (536-78-7,151103-56-9) → methyl α-<1-tosylindol-3-acetic(trans-3,4-dibromo-3-ethylpiperidine)amide-2-yl>acrylate (88839-90-1)

Guidance literature:

Multi-step reaction with 8 steps

1: 99 percent / 72 h / 20 °C

2: NaBH₄ / 1.) abs. ethanol, 0 deg C, 3 h; 2.) 20 deg C, 21 h

3: 83 percent / benzene / 5 h / Heating

4: 93 percent / MeLi, HCl, Et₃N / diethyl ether / 1 h / 0 °C

5: 95 percent / Et₃N / CH₂Cl₂ / 48 h / 20 °C

6: 97 percent / NaBH₄, NH₄Cl / tetrahydrofuran; methanol / 0.08 h / 20 °C

7: 72 percent / 2,4,6-trimethyl benzoic acid / 3 h / 185 °C / Heating

8: 93 percent / Br₂ / CH₂Cl₂ / 0.08 h / -78 °C

With hydrogenchloride; sodium tetrahydroborate; mesitylenecarboxylic acid; methyllithium; bromine; ammonium chloride; triethylamine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; benzene;

DOI:10.1016/S0040-4020(01)88613-0

Reference yield:

indolyl-3-glyoxylyl chloride (22980-09-2) → methyl α-<1-tosylindol-3-acetic(trans-3,4-dibromo-3-ethylpiperidine)amide-2-yl>acrylate (88839-90-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 93 percent / MeLi, HCl, Et₃N / diethyl ether / 1 h / 0 °C

2: 95 percent / Et₃N / CH₂Cl₂ / 48 h / 20 °C

3: 97 percent / NaBH₄, NH₄Cl / tetrahydrofuran; methanol / 0.08 h / 20 °C

4: 72 percent / 2,4,6-trimethyl benzoic acid / 3 h / 185 °C / Heating

5: 93 percent / Br₂ / CH₂Cl₂ / 0.08 h / -78 °C

With hydrogenchloride; sodium tetrahydroborate; mesitylenecarboxylic acid; methyllithium; bromine; ammonium chloride; triethylamine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane;

DOI:10.1016/S0040-4020(01)88613-0

upstream raw materials:

methyl α-<1-tosylindol-3-acetic(1,2,5,6-tetrahydro-3-ethylpyridine)amide-2yl>acrylate

3-ethylpyridine

indolyl-3-glyoxylyl chloride

1-benzyl-3-ethyl-1,2,5,6-tetrahydropyridine

Downstream raw materials:

5-oxo-N_a-14,21-dehydrosecodine

2-oxo-3-methyl-3-carbomethoxy-4-tosyl-cyclopentindole

2-[3-[2-(11-Ethyl-3,5-dioxo-4-phenyl-2,4,6,8-tetraaza-tricyclo[5.2.2.0^2,6]undec-10-en-8-yl)-2-oxo-ethyl]-1-(toluene-4-sulfonyl)-1H-indol-2-yl]-acrylic acid methyl ester

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