bauerine A

Base Information

• Chemical Name: bauerine A
• CAS No.: 156312-09-3
• Molecular Formula: C₁₂H₉ClN₂
• Molecular Weight: 216.67
• Mol file: 156312-09-3.mol

Synonyms:Bauerine A

Chemical Property of bauerine A

Chemical Property:

• Vapor Pressure: 1.38E-06mmHg at 25°C
• Melting Point: 107 °C
• Boiling Point: 399.3°Cat760mmHg
• PKA: 7.55±0.30(Predicted)
• Flash Point: 195.3°C
• PSA: 17.82000
• Density: 1.31g/cm³
• LogP: 3.37990

Purity/Quality:

7-chloro-9-methyl-9H-Pyrido[3,4-b]indole 97.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of bauerine A

There total 15 articles about bauerine A 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: 12.0%

7-chloro-9-methyl-1,2,3,4-tetrahydro-1H-pyrido[3,4-b]indole (606926-91-4) → bauerine A (156312-09-3)

Guidance literature:

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In 1,4-dioxane; for 24h; Heating;

DOI:10.1080/00397910701226228

Reference yield:

N-tert-butyloxycarbonylpiperidin-4-one (79099-07-3) → bauerine A (156312-09-3)

Guidance literature:

Multi-step reaction with 6 steps

1: HMDS

2: 62 percent / Pd(dba)2; Ph₃As; CuI / 1-methyl-pyrrolidin-2-one / 10 h / 50 °C

3: 81 percent / 1,10-phenanthroline; 1,3-bis((diphenylphosphino)propane; CO / Pd(dba)2 / dimethylformamide / 12 h / 80 °C / 4560 Torr

4: 82 percent / NaH / tetrahydrofuran / 4 h / 0 °C

5: aq. HCl / acetic acid / 10 h

6: 55 mg / MnO₂ / toluene / 4 h / 100 °C

With hydrogenchloride; manganese(IV) oxide; copper(l) iodide; 1,10-Phenanthroline; triphenyl-arsane; carbon monoxide; 1,3-bis-(diphenylphosphino)propane; sodium hydride; 1,1,1,3,3,3-hexamethyl-disilazane; bis(dibenzylideneacetone)-palladium⁽⁰⁾; bis(dibenzylideneacetone)-palladium⁽⁰⁾; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; acetic acid; N,N-dimethyl-formamide; toluene; 2: Stille coupling;

DOI:10.1016/S0040-4020(03)00824-X

Reference yield:

4-Trifluoromethanesulfonyloxy-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (138647-49-1) → bauerine A (156312-09-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 62 percent / Pd(dba)2; Ph₃As; CuI / 1-methyl-pyrrolidin-2-one / 10 h / 50 °C

2: 81 percent / 1,10-phenanthroline; 1,3-bis((diphenylphosphino)propane; CO / Pd(dba)2 / dimethylformamide / 12 h / 80 °C / 4560 Torr

3: 82 percent / NaH / tetrahydrofuran / 4 h / 0 °C

4: aq. HCl / acetic acid / 10 h

5: 55 mg / MnO₂ / toluene / 4 h / 100 °C

With hydrogenchloride; manganese(IV) oxide; copper(l) iodide; 1,10-Phenanthroline; triphenyl-arsane; carbon monoxide; 1,3-bis-(diphenylphosphino)propane; sodium hydride; bis(dibenzylideneacetone)-palladium⁽⁰⁾; bis(dibenzylideneacetone)-palladium⁽⁰⁾; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; acetic acid; N,N-dimethyl-formamide; toluene; 1: Stille coupling;

DOI:10.1016/S0040-4020(03)00824-X

upstream raw materials:

7-chloro-9-methyl-1,2,3,4-tetrahydro-1H-pyrido[3,4-b]indole

7-chloro-9-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-one

7-chloro-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-one

3-carboxy-2-piperidone