3-[2-(3-Ethyl-5,6-dihydropyridin-1(2H)-yl)ethyl]-α-methylene-1H-indole-2-acetic acid methyl ester

Base Information

• Chemical Name: 3-[2-(3-Ethyl-5,6-dihydropyridin-1(2H)-yl)ethyl]-α-methylene-1H-indole-2-acetic acid methyl ester
• CAS No.: 27825-42-9
• Molecular Formula: C₂₁H₂₆N₂O₂
• Molecular Weight: 338.45
• Mol file: 27825-42-9.mol

Synonyms:Indole-2-aceticacid, 3-[2-(3-ethyl-5,6-dihydro-1(2H)-pyridyl)ethyl]-a-methylene-, methyl ester (8CI);Secodine

Chemical Property of 3-[2-(3-Ethyl-5,6-dihydropyridin-1(2H)-yl)ethyl]-α-methylene-1H-indole-2-acetic acid methyl ester

Chemical Property:

• Boiling Point: 519.5±50.0 °C(Predicted)
• PKA: 15.79±0.30(Predicted)
• PSA: 45.33000
• Density: 1.117±0.06 g/cm3(Predicted)
• LogP: 3.87660

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 3-[2-(3-Ethyl-5,6-dihydropyridin-1(2H)-yl)ethyl]-α-methylene-1H-indole-2-acetic acid methyl ester

There total 11 articles about 3-[2-(3-Ethyl-5,6-dihydropyridin-1(2H)-yl)ethyl]-α-methylene-1H-indole-2-acetic 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: 76.0%

3-[2-(5-Ethyl-3,6-dihydro-2H-pyridin-1-yl)-ethyl]-2-(1-methoxycarbonyl-vinyl)-indole-1-carboxylic acid 2,2,2-trichloro-1,1-dimethyl-ethyl ester (77612-59-0) → Secodin (27825-42-9)

Guidance literature:

With acetic acid; zinc; In methanol; at 0 ℃; for 0.333333h;

DOI:10.1021/ja00399a053

Reference yield:

indolyl-3-glyoxylyl chloride (22980-09-2) → Secodin (27825-42-9)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.) CH₃Li, 2.) Et₃N / 1.) Et₂O, 0 deg C, 20 min, 2.) 0 deg C, 4 h

2: 80 percent / Et₃N / CH₂Cl₂ / 0.5 h / 0 - 25 °C

3: 63 percent / NaBH₄ / methanol; tetrahydrofuran / 0.33 h / 0 °C

4: 2,4,6-trimethylbenzoic acid / 1.) 210 deg C, 20 min, 2.) 225 deg C, 100 min

5: 71 percent / (CH₃OC₆H₄)2P₂S₄ / benzene / 2 h / Heating

6: 1.) Et₃O⁺BF₄^-, 2.) NaBH₃CN / 1.) CH₂Cl₂, 2.) MeOH, HOAc, 0 deg C

7: 76 percent / powdered zinc, HOAc / methanol / 0.33 h / 0 °C

With Lawessons reagent; sodium tetrahydroborate; mesitylenecarboxylic acid; methyllithium; triethyloxonium fluoroborate; sodium cyanoborohydride; acetic acid; triethylamine; zinc; In tetrahydrofuran; methanol; dichloromethane; benzene;

DOI:10.1021/ja00399a053

Reference yield:

1-benzyl-3-ethyl-1,2,5,6-tetrahydropyridine (60900-14-3) → Secodin (27825-42-9)

Guidance literature:

Multi-step reaction with 8 steps

1: 90 percent / benzene / 20 h / Heating

2: 1.) CH₃Li, 2.) Et₃N / 1.) Et₂O, 0 deg C, 20 min, 2.) 0 deg C, 4 h

3: 80 percent / Et₃N / CH₂Cl₂ / 0.5 h / 0 - 25 °C

4: 63 percent / NaBH₄ / methanol; tetrahydrofuran / 0.33 h / 0 °C

5: 2,4,6-trimethylbenzoic acid / 1.) 210 deg C, 20 min, 2.) 225 deg C, 100 min

6: 71 percent / (CH₃OC₆H₄)2P₂S₄ / benzene / 2 h / Heating

7: 1.) Et₃O⁺BF₄^-, 2.) NaBH₃CN / 1.) CH₂Cl₂, 2.) MeOH, HOAc, 0 deg C

8: 76 percent / powdered zinc, HOAc / methanol / 0.33 h / 0 °C

With Lawessons reagent; sodium tetrahydroborate; mesitylenecarboxylic acid; methyllithium; triethyloxonium fluoroborate; sodium cyanoborohydride; acetic acid; triethylamine; zinc; In tetrahydrofuran; methanol; dichloromethane; benzene;

DOI:10.1021/ja00399a053

upstream raw materials:

3-[2-(5-Ethyl-3,6-dihydro-2H-pyridin-1-yl)-ethyl]-2-(1-methoxycarbonyl-vinyl)-indole-1-carboxylic acid 2,2,2-trichloro-1,1-dimethyl-ethyl ester

indolyl-3-glyoxylyl chloride

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

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