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

Base Information

• Chemical Name: (6R,8S)-5-iodo-6,8-dimethyl-1-(toluene-4-sulfonyl)-1,6,7,8-tetrahydro-1-aza-as-indacene
• CAS No.: 1365987-96-7
• Molecular Formula: C₂₀H₂₀INO₂S
• Molecular Weight: 465.355
• Mol file: 1365987-96-7.mol

Synonyms:

Chemical Property of (6R,8S)-5-iodo-6,8-dimethyl-1-(toluene-4-sulfonyl)-1,6,7,8-tetrahydro-1-aza-as-indacene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (6R,8S)-5-iodo-6,8-dimethyl-1-(toluene-4-sulfonyl)-1,6,7,8-tetrahydro-1-aza-as-indacene

There total 15 articles about (6R,8S)-5-iodo-6,8-dimethyl-1-(toluene-4-sulfonyl)-1,6,7,8-tetrahydro-1-aza-as-indacene 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: 67.0%

(6R,8S)-5-iodo-6,8-dimethyl-1-(toluene-4-sulfonyl)-1,2,3,6,7,8-hexahydro-1-aza-as-indacene (1365987-95-6) → (6R,8S)-5-iodo-6,8-dimethyl-1-(toluene-4-sulfonyl)-1,6,7,8-tetrahydro-1-aza-as-indacene (1365987-96-7)

Guidance literature:

With manganese(III) triacetate dihydrate; acetic acid; at 112 ℃; for 21h; Inert atmosphere; Sealed vessel;

DOI:10.1021/ja3004733

Reference yield:

7-bromo-1H-indole (51417-51-7) → (6R,8S)-5-iodo-6,8-dimethyl-1-(toluene-4-sulfonyl)-1,6,7,8-tetrahydro-1-aza-as-indacene (1365987-96-7)

Guidance literature:

Multi-step reaction with 14 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

9.1: potassium tert-butylate / diethyl ether / 0.5 h / 20 °C / Inert atmosphere

9.2: 12 h / 20 °C / Inert atmosphere

10.1: bis(η3-allyl-μ-chloropalladium(II)); ethene; silver trifluoromethanesulfonate; tris-(o-tolyl)phosphine / dichloromethane / 5 h / 20 °C / 760.05 Torr

11.1: Crabtree's catalyst; hydrogen / dichloromethane / 17 h / 28650.8 Torr / Autoclave

12.1: 5%-palladium/activated carbon; hydrogen / methanol / 17 h / 2766.82 Torr

13.1: iodine; bis-[(trifluoroacetoxy)iodo]benzene / acetonitrile / 2 h / 20 °C / Inert atmosphere; Darkness

14.1: manganese(III) triacetate dihydrate; acetic acid / 21 h / 112 °C / Inert atmosphere; Sealed vessel

With aluminum (III) chloride; sodium chlorite; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tetrapropylammonium perruthennate; sodium dihydrogen phosphate monohydrate; 2-methyl-but-2-ene; oxalyl dichloride; bis(η3-allyl-μ-chloropalladium(II)); Crabtree's catalyst; 18-crown-6 ether; bi(allylnickel bromide); ethene; (R)-2,2'-binaphthoyl-benzyl-(S)-[1-(1-naphthylethyl)]aminoylphosphine; 5%-palladium/activated carbon; potassium tert-butylate; hydrogen; iodine; silver trifluoromethanesulfonate; manganese(III) triacetate dihydrate; potassium hydride; acetic acid; 4-methylmorpholine N-oxide; sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate; N,N-dimethyl-formamide; 9-bora-bicyclo[3.3.1]nonane; tris-(o-tolyl)phosphine; bis-[(trifluoroacetoxy)iodo]benzene; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; diethyl ether; dichloromethane; water; toluene; acetonitrile; tert-butyl alcohol; 1.1: Stille coupling / 8.1: Friedel-Crafts acylation / 9.1: Wittig reaction / 9.2: Wittig reaction / 11.1: Crabtree hydrogenation;

DOI:10.1021/ja3004733

Reference yield:

(S)-3-[1-(toluene-4-sulfonyl)-1H-indol-7-yl]butyric acid chloride → (6R,8S)-5-iodo-6,8-dimethyl-1-(toluene-4-sulfonyl)-1,6,7,8-tetrahydro-1-aza-as-indacene (1365987-96-7)

Guidance literature:

Multi-step reaction with 7 steps

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

2.1: potassium tert-butylate / diethyl ether / 0.5 h / 20 °C / Inert atmosphere

2.2: 12 h / 20 °C / Inert atmosphere

3.1: bis(η3-allyl-μ-chloropalladium(II)); ethene; silver trifluoromethanesulfonate; tris-(o-tolyl)phosphine / dichloromethane / 5 h / 20 °C / 760.05 Torr

4.1: Crabtree's catalyst; hydrogen / dichloromethane / 17 h / 28650.8 Torr / Autoclave

5.1: 5%-palladium/activated carbon; hydrogen / methanol / 17 h / 2766.82 Torr

6.1: iodine; bis-[(trifluoroacetoxy)iodo]benzene / acetonitrile / 2 h / 20 °C / Inert atmosphere; Darkness

7.1: manganese(III) triacetate dihydrate; acetic acid / 21 h / 112 °C / Inert atmosphere; Sealed vessel

With aluminum (III) chloride; bis(η3-allyl-μ-chloropalladium(II)); Crabtree's catalyst; ethene; 5%-palladium/activated carbon; potassium tert-butylate; hydrogen; iodine; silver trifluoromethanesulfonate; manganese(III) triacetate dihydrate; acetic acid; tris-(o-tolyl)phosphine; bis-[(trifluoroacetoxy)iodo]benzene; In methanol; diethyl ether; dichloromethane; acetonitrile; 1.1: Friedel-Crafts acylation / 2.1: Wittig reaction / 2.2: Wittig reaction / 4.1: Crabtree hydrogenation;

DOI:10.1021/ja3004733

upstream raw materials:

7-bromo-1H-indole

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

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

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

Downstream raw materials:

(6R,8S)-cis-trikentrin B