1-(5-methoxy-1H-indol-3-yl)-4-(4-phenyl-3,6-dihydro-2H-pyridin-1-yl)-butane-1,4-dione

Base Information

• Chemical Name: 1-(5-methoxy-1H-indol-3-yl)-4-(4-phenyl-3,6-dihydro-2H-pyridin-1-yl)-butane-1,4-dione
• CAS No.: 227202-63-3
• Molecular Formula: C₂₄H₂₄N₂O₃
• Molecular Weight: 388.466

Synonyms:1-(5-methoxy-1H-indol-3-yl)-4-(4-phenyl-3,6-dihydro-2H-pyridin-1-yl)-butane-1,4-dione

Chemical Property of 1-(5-methoxy-1H-indol-3-yl)-4-(4-phenyl-3,6-dihydro-2H-pyridin-1-yl)-butane-1,4-dione

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Technology Process of 1-(5-methoxy-1H-indol-3-yl)-4-(4-phenyl-3,6-dihydro-2H-pyridin-1-yl)-butane-1,4-dione

There total 2 articles about 1-(5-methoxy-1H-indol-3-yl)-4-(4-phenyl-3,6-dihydro-2H-pyridin-1-yl)-butane-1,4-dione 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: 66.0%

1,2,3,6-tetrahydro-4-phenylpyridine (10338-69-9) + 4-(5-methoxy-indol-3-yl)-4-oxo-butyric acid (100394-00-1) → 1-(5-methoxy-1H-indol-3-yl)-4-(4-phenyl-3,6-dihydro-2H-pyridin-1-yl)-butane-1,4-dione (227202-63-3)

Guidance literature:

With N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; for 2h; Ambient temperature;

DOI:10.1016/S0960-894X(99)00135-3

Reference yield:

5-methoxylindole (1006-94-6) → 1-(5-methoxy-1H-indol-3-yl)-4-(4-phenyl-3,6-dihydro-2H-pyridin-1-yl)-butane-1,4-dione (227202-63-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) MeMgBr, 2.) anisole / 1.) Et₂O, RT, 2.) 100 deg C, 2 h

2: 66 percent / EDC, DIPEA / dimethylformamide / 2 h / Ambient temperature

With methylmagnesium bromide; methoxybenzene; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide;

DOI:10.1016/S0960-894X(99)00135-3

Reference yield: 85.0%

1-(5-methoxy-1H-indol-3-yl)-4-(4-phenyl-3,6-dihydro-2H-pyridin-1-yl)-butane-1,4-dione (227202-63-3) → 5-methoxy-3-[3-(1,2,3,6-tetrahydro-4-phenyl-1-pyridyl)butyl]indole (143682-61-5)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; for 1h; Heating;

DOI:10.1016/S0960-894X(99)00135-3

upstream raw materials:

1,2,3,6-tetrahydro-4-phenylpyridine

4-(5-methoxy-indol-3-yl)-4-oxo-butyric acid

5-methoxylindole

Downstream raw materials:

5-methoxy-3-[3-(1,2,3,6-tetrahydro-4-phenyl-1-pyridyl)butyl]indole

roxindole

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