(8S)-8-methyl-1-(toluene-4-sulfonyl)-7,8-dihydro-1H-1-aza-as-indacen-6-one

Base Information

• Chemical Name: (8S)-8-methyl-1-(toluene-4-sulfonyl)-7,8-dihydro-1H-1-aza-as-indacen-6-one
• CAS No.: 1365987-82-1
• Molecular Formula: C₁₉H₁₇NO₃S
• Molecular Weight: 339.415
• Mol file: 1365987-82-1.mol

Synonyms:(8S)-8-methyl-1-(toluene-4-sulfonyl)-7,8-dihydro-1H-1-aza-as-indacen-6-one

Chemical Property of (8S)-8-methyl-1-(toluene-4-sulfonyl)-7,8-dihydro-1H-1-aza-as-indacen-6-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (8S)-8-methyl-1-(toluene-4-sulfonyl)-7,8-dihydro-1H-1-aza-as-indacen-6-one

There total 9 articles about (8S)-8-methyl-1-(toluene-4-sulfonyl)-7,8-dihydro-1H-1-aza-as-indacen-6-one 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:

(S)-3-[1-(toluene-4-sulfonyl)-1H-indol-7-yl]butyric acid chloride → (8S)-8-methyl-1-(toluene-4-sulfonyl)-7,8-dihydro-1H-1-aza-as-indacen-6-one (1365987-82-1)

Guidance literature:

With aluminum (III) chloride; In dichloromethane; at 0 ℃; for 0.833333h; Inert atmosphere; Reflux;

DOI:10.1021/ja3004733

Reference yield:

7-bromo-1H-indole (51417-51-7) → (8S)-8-methyl-1-(toluene-4-sulfonyl)-7,8-dihydro-1H-1-aza-as-indacen-6-one (1365987-82-1)

Guidance literature:

Multi-step reaction with 8 steps

1.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / toluene / 2 h / Inert atmosphere; Reflux

2.1: bi(allylnickel bromide); (R)-2,2'-binaphthoyl-benzyl-(S)-[1-(1-naphthylethyl)]aminoylphosphine; sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate / dichloromethane / 3.03 h / -78 °C / 760.05 Torr

3.1: 18-crown-6 ether; potassium hydride / 1,2-dimethoxyethane / 0.5 h / 0 - 20 °C / Inert atmosphere

3.2: 14 h / 0 - 20 °C / Inert atmosphere

4.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 1.5 h / 0 - 20 °C / Inert atmosphere

4.2: 0.5 h / 0 - 20 °C / Inert atmosphere

5.1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / dichloromethane / 1.33 h / 20 °C / Inert atmosphere; Molecular sieve

6.1: sodium chlorite; sodium dihydrogen phosphate monohydrate; 2-methyl-but-2-ene / tetrahydrofuran; water; tert-butyl alcohol / 1 h / 0 - 20 °C

7.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere

8.1: aluminum (III) chloride / dichloromethane / 0.83 h / 0 °C / Inert atmosphere; Reflux

With aluminum (III) chloride; sodium chlorite; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tetrapropylammonium perruthennate; sodium dihydrogen phosphate monohydrate; 2-methyl-but-2-ene; oxalyl dichloride; 18-crown-6 ether; bi(allylnickel bromide); (R)-2,2'-binaphthoyl-benzyl-(S)-[1-(1-naphthylethyl)]aminoylphosphine; potassium hydride; 4-methylmorpholine N-oxide; sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate; N,N-dimethyl-formamide; 9-bora-bicyclo[3.3.1]nonane; In tetrahydrofuran; 1,2-dimethoxyethane; dichloromethane; water; toluene; tert-butyl alcohol; 1.1: Stille coupling / 8.1: Friedel-Crafts acylation;

DOI:10.1021/ja3004733

Reference yield:

7-ethenyl-1H-indole (94239-08-4) → (8S)-8-methyl-1-(toluene-4-sulfonyl)-7,8-dihydro-1H-1-aza-as-indacen-6-one (1365987-82-1)

Guidance literature:

Multi-step reaction with 7 steps

1.1: bi(allylnickel bromide); (R)-2,2'-binaphthoyl-benzyl-(S)-[1-(1-naphthylethyl)]aminoylphosphine; sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate / dichloromethane / 3.03 h / -78 °C / 760.05 Torr

2.1: 18-crown-6 ether; potassium hydride / 1,2-dimethoxyethane / 0.5 h / 0 - 20 °C / Inert atmosphere

2.2: 14 h / 0 - 20 °C / Inert atmosphere

3.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 1.5 h / 0 - 20 °C / Inert atmosphere

3.2: 0.5 h / 0 - 20 °C / Inert atmosphere

4.1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / dichloromethane / 1.33 h / 20 °C / Inert atmosphere; Molecular sieve

5.1: sodium chlorite; sodium dihydrogen phosphate monohydrate; 2-methyl-but-2-ene / tetrahydrofuran; water; tert-butyl alcohol / 1 h / 0 - 20 °C

6.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere

7.1: aluminum (III) chloride / dichloromethane / 0.83 h / 0 °C / Inert atmosphere; Reflux

With aluminum (III) chloride; sodium chlorite; tetrapropylammonium perruthennate; sodium dihydrogen phosphate monohydrate; 2-methyl-but-2-ene; oxalyl dichloride; 18-crown-6 ether; bi(allylnickel bromide); (R)-2,2'-binaphthoyl-benzyl-(S)-[1-(1-naphthylethyl)]aminoylphosphine; potassium hydride; 4-methylmorpholine N-oxide; sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate; N,N-dimethyl-formamide; 9-bora-bicyclo[3.3.1]nonane; In tetrahydrofuran; 1,2-dimethoxyethane; dichloromethane; water; tert-butyl alcohol; 7.1: Friedel-Crafts acylation;

DOI:10.1021/ja3004733

upstream raw materials:

7-bromo-1H-indole

(S)-7-(3-but-1-enyl)-1H-indole

(S)-7-(2-but-3-enyl)-1-(toluene-4-sulfonyl)-1H-indole

(S)-3-[1-(toluene-4-sulfonyl)-1H-indol-7-yl]butan-1-ol

Downstream raw materials:

(8S)-6,8-dimethyl-1-(toluene-4-sulfonyl)-1,8-dihydro-1-aza-as-indacene

(6R,8S)-6,8-dimethyl-1-(toluene-4-sulfonyl)-1,6,7,8-tetrahydro-1-aza-as-indacene

(6R,8S)-6,8-dimethyl-1-(toluene-4-sulfonyl)-1,2,3,6,7,8-hexahydro-1-aza-as-indacene

(6R,8S)-5-iodo-6,8-dimethyl-1-(toluene-4-sulfonyl)-1,2,3,6,7,8-hexahydro-1-aza-as-indacene