4-[3-methyl-1-(toluene-4-sulfonyl)-5-vinyl-1H-indol-4-yl]-but-2-enoic acid methyl ester

Base Information

Chemical Name:4-[3-methyl-1-(toluene-4-sulfonyl)-5-vinyl-1H-indol-4-yl]-but-2-enoic acid methyl ester
CAS No.:891718-75-5
Molecular Formula:C₂₃H₂₃NO₄S
Molecular Weight:409.506
Hs Code.:

4-[3-methyl-1-(toluene-4-sulfonyl)-5-vinyl-1<i>H</i>-indol-4-yl]-but-2-enoic acid methyl ester

Synonyms:4-[3-methyl-1-(toluene-4-sulfonyl)-5-vinyl-1H-indol-4-yl]-but-2-enoic acid methyl ester

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Chemical Property of 4-[3-methyl-1-(toluene-4-sulfonyl)-5-vinyl-1H-indol-4-yl]-but-2-enoic acid methyl ester

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Technology Process of 4-[3-methyl-1-(toluene-4-sulfonyl)-5-vinyl-1H-indol-4-yl]-but-2-enoic acid methyl ester

There total 12 articles about 4-[3-methyl-1-(toluene-4-sulfonyl)-5-vinyl-1H-indol-4-yl]-but-2-enoic acid methyl 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: 87.0%

: 891718-67-5
[3-methyl-1-(toluene-4-sulfonyl)-5-vinyl-1H-indol-4-yl]-acetaldehyde

: 5927-18-4
trimethyl phosphonoacetate

: 891718-75-5
4-[3-methyl-1-(toluene-4-sulfonyl)-5-vinyl-1H-indol-4-yl]-but-2-enoic acid methyl ester

Guidance literature:: trimethyl phosphonoacetate; With n-butyllithium; In tetrahydrofuran; at 0 ℃; for 0.5h;

[3-methyl-1-(toluene-4-sulfonyl)-5-vinyl-1H-indol-4-yl]-acetaldehyde; In tetrahydrofuran; at 0 - 20 ℃; for 1.5h;
DOI:10.1021/ol060338j

Reference yield:

: 863582-11-0
N-(4-hydroxy-8-methyl-5,8-dihydro-naphthalen-1-yl)-4-methyl-benzenesulfonamide

: 891718-75-5
4-[3-methyl-1-(toluene-4-sulfonyl)-5-vinyl-1H-indol-4-yl]-but-2-enoic acid methyl ester

Guidance literature:: Multi-step reaction with 10 steps

1.1: NaH / tetrahydrofuran

2.1: NMO / OsO₄

3.1: NaIO₄; SiO₂

4.1: H₂SO₄ / tetrahydrofuran

5.1: NaBH₄ / tetrahydrofuran; methanol / 1 h / 0 °C

6.1: 5.03 g / NEt₃ / tetrahydrofuran / 1 h / 0 °C

7.1: 90 percent / LiCl; BHT / Pd(PPh₃)2Cl₂ / dimethylformamide / 24 h / 125 °C

8.1: K₂CO₃; MeOH; H₂O / acetone / 2 h / 20 °C

9.1: 2.64 g / IBX / dimethylsulfoxide; tetrahydrofuran / 20 °C

10.1: n-BuLi / tetrahydrofuran / 0.5 h / 0 °C

10.2: 87 percent / tetrahydrofuran / 1.5 h / 0 - 20 °C

With methanol; sodium tetrahydroborate; sodium periodate; n-butyllithium; N-methyl-2-indolinone; 2,6-di-tert-butyl-4-methyl-phenol; sulfuric acid; water; silica gel; sodium hydride; potassium carbonate; triethylamine; lithium chloride; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; bis-triphenylphosphine-palladium(II) chloride; osmium(VIII) oxide; In tetrahydrofuran; methanol; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; 4.1: Plieninger indolization / 7.1: Stille coupling / 10.2: Horner-Wadsworth-Emmons olefination;
DOI:10.1021/ol060338j

Reference yield:

: 863582-27-8
trifluoro-methanesulfonic acid 5-methyl-4-(toluene-4-sulfonylamino)-5,8-dihydro-naphthalen-1-yl ester

: 891718-75-5
4-[3-methyl-1-(toluene-4-sulfonyl)-5-vinyl-1H-indol-4-yl]-but-2-enoic acid methyl ester

Guidance literature:: Multi-step reaction with 9 steps

1.1: NMO / OsO₄

2.1: NaIO₄; SiO₂

3.1: H₂SO₄ / tetrahydrofuran

4.1: NaBH₄ / tetrahydrofuran; methanol / 1 h / 0 °C

5.1: 5.03 g / NEt₃ / tetrahydrofuran / 1 h / 0 °C

6.1: 90 percent / LiCl; BHT / Pd(PPh₃)2Cl₂ / dimethylformamide / 24 h / 125 °C

7.1: K₂CO₃; MeOH; H₂O / acetone / 2 h / 20 °C

8.1: 2.64 g / IBX / dimethylsulfoxide; tetrahydrofuran / 20 °C

9.1: n-BuLi / tetrahydrofuran / 0.5 h / 0 °C

9.2: 87 percent / tetrahydrofuran / 1.5 h / 0 - 20 °C

With methanol; sodium tetrahydroborate; sodium periodate; n-butyllithium; N-methyl-2-indolinone; 2,6-di-tert-butyl-4-methyl-phenol; sulfuric acid; water; silica gel; potassium carbonate; triethylamine; lithium chloride; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; bis-triphenylphosphine-palladium(II) chloride; osmium(VIII) oxide; In tetrahydrofuran; methanol; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; 3.1: Plieninger indolization / 6.1: Stille coupling / 9.2: Horner-Wadsworth-Emmons olefination;
DOI:10.1021/ol060338j