9H-Pyrido[3,4-b]indole-1-carbonitrile, 4-methoxy-9-(phenylmethyl)-

Base Information

• Chemical Name: 9H-Pyrido[3,4-b]indole-1-carbonitrile, 4-methoxy-9-(phenylmethyl)-
• CAS No.: 137937-02-1
• Molecular Formula: C20H15N3O
• Molecular Weight: 313.359
• Mol file: 137937-02-1.mol

Synonyms:

Chemical Property of 9H-Pyrido[3,4-b]indole-1-carbonitrile, 4-methoxy-9-(phenylmethyl)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 9H-Pyrido[3,4-b]indole-1-carbonitrile, 4-methoxy-9-(phenylmethyl)-

There total 10 articles about 9H-Pyrido[3,4-b]indole-1-carbonitrile, 4-methoxy-9-(phenylmethyl)- 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: 62.0%

diethyl cyanophosphonate (2942-58-7) + 9-benzyl-4-methoxy-β-carboline-N-oxide (137937-01-0) → 9-benzyl-1-cyano-4-methoxy-β-carboline (137937-02-1)

Guidance literature:

With triethylamine; In 1,4-dioxane; Heating;

DOI:10.1248/cpb.39.2170

Reference yield:

ethyl 1-benzyl-1H-indole-2-carboxylate (17017-66-2) → 9-benzyl-1-cyano-4-methoxy-β-carboline (137937-02-1)

Guidance literature:

Multi-step reaction with 8 steps

1: 99 percent / LiAlH₄ / tetrahydrofuran / 0.5 h / Ambient temperature

2: 96 percent / MnO₂ / CH₂Cl₂ / 6 h / Ambient temperature

3: 79 percent / triethylamine, NaBH₃CN / ethanol / 14 h / Ambient temperature

4: 99 percent / ethyl formate / 20 h / Ambient temperature

5: 94 percent / methanesulfonic acid / 1 h / 70 °C / other reagent: polyphosphoric acid

6: 75 percent / p-toluenesulfonic acid monohydrate, chloranil / benzene / 15 h / Ambient temperature; other reagent: benzoquinone

7: 98 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 4 h / Ambient temperature

8: 62 percent / triethylamine / acetonitrile / 3 h / Heating

With manganese(IV) oxide; lithium aluminium tetrahydride; methanesulfonic acid; chloranil; sodium cyanoborohydride; toluene-4-sulfonic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; formic acid ethyl ester; In tetrahydrofuran; ethanol; dichloromethane; acetonitrile; benzene;

DOI:10.1016/S0040-4020(96)01112-X

Reference yield:

9-benzyl-2-formyl-4-oxo-1,2,3,4-tetrahydro-β-carboline (137936-99-3) → 9-benzyl-1-cyano-4-methoxy-β-carboline (137937-02-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 75 percent / p-toluenesulfonic acid monohydrate, chloranil / benzene / 15 h / Ambient temperature; other reagent: benzoquinone

2: 98 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 4 h / Ambient temperature

3: 62 percent / triethylamine / acetonitrile / 3 h / Heating

With chloranil; toluene-4-sulfonic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; acetonitrile; benzene;

DOI:10.1016/S0040-4020(96)01112-X

upstream raw materials:

diethyl cyanophosphonate

9-benzyl-4-methoxy-β-carboline-N-oxide

ethyl 1-benzyl-1H-indole-2-carboxylate

1-benzylindole-2-carbaldehyde

Downstream raw materials:

1-acetyl-9-benzyl-4-methoxy-β-carboline