5-<1-hydroxy-2-<(1-methyl-3-phenylpropyl)-amino>ethyl>-1-methyl-1H-indole-7-carboxamide

Base Information

• Chemical Name: 5-<1-hydroxy-2-<(1-methyl-3-phenylpropyl)-amino>ethyl>-1-methyl-1H-indole-7-carboxamide
• CAS No.: 101544-37-0
• Molecular Formula: C₂₂H₂₇N₃O₂
• Molecular Weight: 365.475

Synonyms:5-<1-hydroxy-2-<(1-methyl-3-phenylpropyl)-amino>ethyl>-1-methyl-1H-indole-7-carboxamide

Chemical Property of 5-<1-hydroxy-2-<(1-methyl-3-phenylpropyl)-amino>ethyl>-1-methyl-1H-indole-7-carboxamide

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of 5-<1-hydroxy-2-<(1-methyl-3-phenylpropyl)-amino>ethyl>-1-methyl-1H-indole-7-carboxamide

There total 12 articles about 5-<1-hydroxy-2-<(1-methyl-3-phenylpropyl)-amino>ethyl>-1-methyl-1H-indole-7-carboxamide 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:

1-Acetyl-2,3-dihydro-1H-indole (16078-30-1) → 5-<1-hydroxy-2-<(1-methyl-3-phenylpropyl)-amino>ethyl>-1-methyl-1H-indole-7-carboxamide (101544-37-0)

Guidance literature:

Multi-step reaction with 12 steps

1: 1.) aluminum chloride / 1.) 1,2-dichloroethane, 20 min, 2.) 1,2-dichloroethane, 50 deg C, 1 h

2: dimethylformamide / 2 h / 60 °C

3: NaBH₄ / ethanol / 1.) RT, 4.5 h, 2.) 50 deg C, 1 h

4: 94.5 percent / pyridine / Ambient temperature

5: 85.9 percent / 90percent nitric acid / acetic acid / 6 h / Ambient temperature

6: 93 percent / acetic acid, zinc dust / ethanol / 0.5 h / Ambient temperature

7: 1.) a) hydrochloric acid, sodium nitrite, b) aq. HBF₄, 2.) potassium cyanide / 1.) -5 deg C, 20 min, 2.) DMSO, 20 deg C, 1.5 h

8: 5N aq. sodium hydroxide / ethanol / 1.5 h / 20 °C

9: 35percent hydrogen peroxide / dimethylsulfoxide / 0.25 h / 15 °C

10: 91 percent / manganese(IV) oxide / tetrahydrofuran / 9 h / Ambient temperature

11: 1.) sodium hydride / 1.) dimethylformamide, RT, 1 h, 2.) dimethylformamide, 2 h

12: 800 mg / acetic acid, H₂ / 10percent Pd/C, PtO₂ / methanol

With pyridine; hydrogenchloride; potassium cyanide; manganese(IV) oxide; sodium hydroxide; sodium tetrahydroborate; tetrafluoroboric acid; aluminium trichloride; hydrogen; dihydrogen peroxide; nitric acid; sodium hydride; acetic acid; zinc; sodium nitrite; platinum(IV) oxide; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; acetic acid; dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1021/jm00156a019

Reference yield:

2-chloro-1-(1-acetyl-2,3-dihydroindole-5-yl)ethanone (76139-03-2) → 5-<1-hydroxy-2-<(1-methyl-3-phenylpropyl)-amino>ethyl>-1-methyl-1H-indole-7-carboxamide (101544-37-0)

Guidance literature:

Multi-step reaction with 11 steps

1: dimethylformamide / 2 h / 60 °C

2: NaBH₄ / ethanol / 1.) RT, 4.5 h, 2.) 50 deg C, 1 h

3: 94.5 percent / pyridine / Ambient temperature

4: 85.9 percent / 90percent nitric acid / acetic acid / 6 h / Ambient temperature

5: 93 percent / acetic acid, zinc dust / ethanol / 0.5 h / Ambient temperature

6: 1.) a) hydrochloric acid, sodium nitrite, b) aq. HBF₄, 2.) potassium cyanide / 1.) -5 deg C, 20 min, 2.) DMSO, 20 deg C, 1.5 h

7: 5N aq. sodium hydroxide / ethanol / 1.5 h / 20 °C

8: 35percent hydrogen peroxide / dimethylsulfoxide / 0.25 h / 15 °C

9: 91 percent / manganese(IV) oxide / tetrahydrofuran / 9 h / Ambient temperature

10: 1.) sodium hydride / 1.) dimethylformamide, RT, 1 h, 2.) dimethylformamide, 2 h

11: 800 mg / acetic acid, H₂ / 10percent Pd/C, PtO₂ / methanol

With pyridine; hydrogenchloride; potassium cyanide; manganese(IV) oxide; sodium hydroxide; sodium tetrahydroborate; tetrafluoroboric acid; hydrogen; dihydrogen peroxide; nitric acid; sodium hydride; acetic acid; zinc; sodium nitrite; platinum(IV) oxide; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; acetic acid; dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1021/jm00156a019

Reference yield:

5-<1-hydroxy-2-ethyl>-1H-indole-7-carboxamide (101544-45-0) → 5-<1-hydroxy-2-<(1-methyl-3-phenylpropyl)-amino>ethyl>-1-methyl-1H-indole-7-carboxamide (101544-37-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) sodium hydride / 1.) dimethylformamide, RT, 1 h, 2.) dimethylformamide, 2 h

2: 800 mg / acetic acid, H₂ / 10percent Pd/C, PtO₂ / methanol

With hydrogen; sodium hydride; acetic acid; platinum(IV) oxide; palladium on activated charcoal; In methanol;

DOI:10.1021/jm00156a019

upstream raw materials:

4-Phenyl-2-butanone

5-<1-hydroxy-2-ethyl>-1-methyl-1H-indole-7-carboxamide

1-Acetyl-2,3-dihydro-1H-indole

2-chloro-1-(1-acetyl-2,3-dihydroindole-5-yl)ethanone

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