trifluoromethanesulfonic acid 2-(methyl{4-[methyl(toluene-4-sulfonyl)amino]but-2-ynoyl}amino)phenyl ester

Base Information

• Chemical Name: trifluoromethanesulfonic acid 2-(methyl{4-[methyl(toluene-4-sulfonyl)amino]but-2-ynoyl}amino)phenyl ester
• CAS No.: 582315-16-0
• Molecular Formula: C₂₀H₁₉F₃N₂O₆S₂
• Molecular Weight: 504.508
• Mol file: 582315-16-0.mol

Synonyms:trifluoromethanesulfonic acid 2-(methyl{4-[methyl(toluene-4-sulfonyl)amino]but-2-ynoyl}amino)phenyl ester

Chemical Property of trifluoromethanesulfonic acid 2-(methyl{4-[methyl(toluene-4-sulfonyl)amino]but-2-ynoyl}amino)phenyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of trifluoromethanesulfonic acid 2-(methyl{4-[methyl(toluene-4-sulfonyl)amino]but-2-ynoyl}amino)phenyl ester

There total 1 articles about trifluoromethanesulfonic acid 2-(methyl{4-[methyl(toluene-4-sulfonyl)amino]but-2-ynoyl}amino)phenyl ester 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: 41.0%

methyl(propargyl)amine (35161-71-8) + N,N-phenylbistrifluoromethane-sulfonimide (37595-74-7) + 3-methylbenzo[d]oxazol-2(3H)-one (21892-80-8) + p-toluenesulfonyl chloride (98-59-9) → trifluoromethanesulfonic acid 2-(methyl{4-[methyl(toluene-4-sulfonyl)amino]but-2-ynoyl}amino)phenyl ester (582315-16-0)

Guidance literature:

Multistep reaction;

DOI:10.1016/S0040-4020(03)00855-X

Reference yield:

trifluoromethanesulfonic acid 2-(methyl{4-[methyl(toluene-4-sulfonyl)amino]but-2-ynoyl}amino)phenyl ester (582315-16-0) + 7-iodo-1,1',8-trimethyl-2,3,8,8aS,2',3',8',8'aR-octahydro-1H,1'H-[3aS,3'aS]bipyrrolo[2,3-b]indole (582315-07-9) → Trifluoro-methanesulfonic acid 2-{methyl-[(Z)-4-[methyl-(toluene-4-sulfonyl)-amino]-2-((3aS,8aS,3'aS,8'aR)-1,1',8'-trimethyl-2,3,8,8a,2',3',8',8'a-octahydro-1H,1'H-[3a,3'a]bi[pyrrolo[2,3-b]indolyl]-7-yl)-but-2-enoyl]-amino}-phenyl ester (582315-02-4)

Guidance literature:

trifluoromethanesulfonic acid 2-(methyl{4-[methyl(toluene-4-sulfonyl)amino]but-2-ynoyl}amino)phenyl ester; With tri-n-butyl-tin hydride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; at 0 ℃; for 2h;

7-iodo-1,1',8-trimethyl-2,3,8,8aS,2',3',8',8'aR-octahydro-1H,1'H-[3aS,3'aS]bipyrrolo[2,3-b]indole; With 1-methyl-pyrrolidin-2-one; copper(l) iodide; trifuran-2-yl-phosphane; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; at 20 ℃; for 36h;

DOI:10.1016/S0040-4020(03)00855-X

Reference yield:

trifluoromethanesulfonic acid 2-(methyl{4-[methyl(toluene-4-sulfonyl)amino]but-2-ynoyl}amino)phenyl ester (582315-16-0) → 4,N-dimethyl-N-{2-[1-methyl-2-oxo-3-(1,1',8'-trimethyl-2,3,8,8a,2',3',8',8'a-octahydro-1H,1'H-[3a,3'a]bi[pyrrolo[2,3-b]indolyl]-7-yl)-2,3-dihydro-1H-indol-3-yl]-ethyl}-benzenesulfonamide

Guidance literature:

Multi-step reaction with 2 steps

1.1: Bu₃SnH / Pd(PPh₃)4 / tetrahydrofuran / 2 h / 0 °C

1.2: 0.162 g / P(2-furyl)3; NMP; CuI / Pd₂(dba)3*CHCl₃ / 36 h / 20 °C

2.1: (R)-tol-BINAP; 1,2,2,6,6-pentamethylpiperidine / Pd(OAc)2 / acetonitrile / 18 h / 80 °C

2.2: H₂ / Pd(OH)2/C / ethanol / 48 h / 80 °C / 77572.2 Torr

With 1,2,2,6,6-pentamethylpiperidine; (R)-2,2'-bis[bis(3-methylphenyl)phosphino]-1,1'-binaphthyl; tri-n-butyl-tin hydride; palladium diacetate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; acetonitrile; 1.2: Stille coupling / 2.1: Heck cyclization;

DOI:10.1016/S0040-4020(03)00855-X

upstream raw materials:

methyl(propargyl)amine

N,N-phenylbistrifluoromethane-sulfonimide

3-methylbenzo[d]oxazol-2(3H)-one

p-toluenesulfonyl chloride

Downstream raw materials:

Trifluoro-methanesulfonic acid 2-{methyl-[(Z)-4-[methyl-(toluene-4-sulfonyl)-amino]-2-((3aS,8aS,3'aS,8'aR)-1,1',8'-trimethyl-2,3,8,8a,2',3',8',8'a-octahydro-1H,1'H-[3a,3'a]bi[pyrrolo[2,3-b]indolyl]-7-yl)-but-2-enoyl]-amino}-phenyl ester