1H-Indole, 2-[(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ylidene)methyl]-1-(phenylsulfon yl)-

Base Information

• Chemical Name: 1H-Indole, 2-[(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ylidene)methyl]-1-(phenylsulfon yl)-
• CAS No.: 143618-90-0
• Molecular Formula: C21H17NO6S
• Molecular Weight: 411.435
• Mol file: 143618-90-0.mol

Synonyms:

Chemical Property of 1H-Indole, 2-[(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ylidene)methyl]-1-(phenylsulfon yl)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1H-Indole, 2-[(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ylidene)methyl]-1-(phenylsulfon yl)-

There total 1 articles about 1H-Indole, 2-[(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ylidene)methyl]-1-(phenylsulfon yl)- 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-benzenesulfonylindole (40899-71-6) + 5-(ethoxymethylene)-2,2-dimethyl-1,3-dioxane-4,6-dione (15568-86-2) → 5-<<-2-<1-(benzenesulfonyl)indolyl>>methylidene>-2,2-dimethyl-1,3-dioxane-4,6-dione (143618-90-0)

Guidance literature:

With lithium diisopropyl amide; Yield given. Multistep reaction; 1.) THF, hexane, 0 deg C, 30 min, 2.) THF, 1 h;

DOI:10.1021/jo00048a026

Reference yield:

5-<<-2-<1-(benzenesulfonyl)indolyl>>methylidene>-2,2-dimethyl-1,3-dioxane-4,6-dione (143618-90-0) → Tryptophan p 2 acetate (72254-58-1,75074-77-0)

Guidance literature:

Multi-step reaction with 9 steps

1: 1.5 h / 180 °C

2: 20percent aqueous NaOH / ethanol / 12 h / Heating

3: 86 percent / diethyl ether; methanol; CHCl₃ / 0.17 h / 0 °C

4: 86 percent / AcOH, polyphosphoric acid / acetonitrile / 12 h / Ambient temperature

5: 77 percent / NH₂OH*HCl, NaOAc / ethanol / 1 h / Heating

6: 51 percent / xylene / 24 h / Heating

7: 95 percent / 10percent aqueous NaOH / ethanol / 1 h / Heating

8: 98 percent / diphenylphosphoryl azide (DPPA), triethylamine / 0.5 h / 80 °C

9: 81 percent / AcOH / H₂O / 1 h / 80 °C

With sodium hydroxide; PPA; diphenylphosphoranyl azide; hydroxylamine hydrochloride; sodium acetate; acetic acid; triethylamine; In methanol; diethyl ether; ethanol; chloroform; water; acetonitrile; xylene;

DOI:10.1021/jo00048a026

Reference yield:

5-<<-2-<1-(benzenesulfonyl)indolyl>>methylidene>-2,2-dimethyl-1,3-dioxane-4,6-dione (143618-90-0) → 1-methyl-5H-pyrido<4,3-b>indole-3-carboxylic acid (65032-81-7)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.5 h / 180 °C

2: 20percent aqueous NaOH / ethanol / 12 h / Heating

3: 86 percent / diethyl ether; methanol; CHCl₃ / 0.17 h / 0 °C

4: 86 percent / AcOH, polyphosphoric acid / acetonitrile / 12 h / Ambient temperature

5: 77 percent / NH₂OH*HCl, NaOAc / ethanol / 1 h / Heating

6: 51 percent / xylene / 24 h / Heating

7: 95 percent / 10percent aqueous NaOH / ethanol / 1 h / Heating

With sodium hydroxide; PPA; hydroxylamine hydrochloride; sodium acetate; acetic acid; In methanol; diethyl ether; ethanol; chloroform; acetonitrile; xylene;

DOI:10.1021/jo00048a026

upstream raw materials:

1-benzenesulfonylindole

5-(ethoxymethylene)-2,2-dimethyl-1,3-dioxane-4,6-dione

Downstream raw materials:

Tryptophan p 2 acetate

1-methyl-5H-pyrido<4,3-b>indole-3-carboxylic acid