3-methyl-4-(4-oxo-pent-2-enyl)-1-(toluene-4-sulfonyl)-1H-indole-5-carbaldehyde

Base Information

Chemical Name:3-methyl-4-(4-oxo-pent-2-enyl)-1-(toluene-4-sulfonyl)-1H-indole-5-carbaldehyde
CAS No.:891719-07-6
Molecular Formula:C₂₂H₂₁NO₄S
Molecular Weight:395.479
Hs Code.:

3-methyl-4-(4-oxo-pent-2-enyl)-1-(toluene-4-sulfonyl)-1<i>H</i>-indole-5-carbaldehyde

Synonyms:3-methyl-4-(4-oxo-pent-2-enyl)-1-(toluene-4-sulfonyl)-1H-indole-5-carbaldehyde

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Chemical Property of 3-methyl-4-(4-oxo-pent-2-enyl)-1-(toluene-4-sulfonyl)-1H-indole-5-carbaldehyde

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Technology Process of 3-methyl-4-(4-oxo-pent-2-enyl)-1-(toluene-4-sulfonyl)-1H-indole-5-carbaldehyde

There total 14 articles about 3-methyl-4-(4-oxo-pent-2-enyl)-1-(toluene-4-sulfonyl)-1H-indole-5-carbaldehyde 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:

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

: 891719-07-6
3-methyl-4-(4-oxo-pent-2-enyl)-1-(toluene-4-sulfonyl)-1H-indole-5-carbaldehyde

Guidance literature:: Multi-step reaction with 12 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: 88 percent / tetrahydrofuran / 2.5 h / 0 - 20 °C

11.1: NMO; H₂O / osmium tetroxide / tetrahydrofuran / 5 h

12.1: 1.89 g / NaIO₄/SiO₂ gel / CH₂Cl₂

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; dichloromethane; 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

: 891719-07-6
3-methyl-4-(4-oxo-pent-2-enyl)-1-(toluene-4-sulfonyl)-1H-indole-5-carbaldehyde

Guidance literature:: Multi-step reaction with 11 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: 88 percent / tetrahydrofuran / 2.5 h / 0 - 20 °C

10.1: NMO; H₂O / osmium tetroxide / tetrahydrofuran / 5 h

11.1: 1.89 g / NaIO₄/SiO₂ gel / CH₂Cl₂

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; dichloromethane; 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

Reference yield:

: 863582-36-9
trifluoro-methanesulfonic acid 3-methyl-4-(2-oxo-ethyl)-1-(toluene-4-sulfonyl)-1H-indol-5-yl ester

: 891719-07-6
3-methyl-4-(4-oxo-pent-2-enyl)-1-(toluene-4-sulfonyl)-1H-indole-5-carbaldehyde

Guidance literature:: Multi-step reaction with 8 steps

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

2.1: 5.03 g / NEt₃ / tetrahydrofuran / 1 h / 0 °C

3.1: 90 percent / LiCl; BHT / Pd(PPh₃)2Cl₂ / dimethylformamide / 24 h / 125 °C

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

5.1: 2.64 g / IBX / dimethylsulfoxide; tetrahydrofuran / 20 °C

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

6.2: 88 percent / tetrahydrofuran / 2.5 h / 0 - 20 °C

7.1: NMO; H₂O / osmium tetroxide / tetrahydrofuran / 5 h

8.1: 1.89 g / NaIO₄/SiO₂ gel / CH₂Cl₂

With methanol; sodium tetrahydroborate; sodium periodate; n-butyllithium; N-methyl-2-indolinone; 2,6-di-tert-butyl-4-methyl-phenol; 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; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; 3.1: Stille coupling / 6.2: Horner-Wadsworth-Emmons olefination;
DOI:10.1021/ol060338j