4-[N-(methyl)-N-propargyl]amino-5,5-ethylenedioxy-1-(toluene-4-sulfonyl)-3,4-dihydro-1H-benzo[c,d]indole

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Chemical Name:4-[N-(methyl)-N-propargyl]amino-5,5-ethylenedioxy-1-(toluene-4-sulfonyl)-3,4-dihydro-1H-benzo[c,d]indole
CAS No.:849413-50-9
Molecular Formula:C₂₄H₂₄N₂O₄S
Molecular Weight:436.532
Hs Code.:

Synonyms:4-[N-(methyl)-N-propargyl]amino-5,5-ethylenedioxy-1-(toluene-4-sulfonyl)-3,4-dihydro-1H-benzo[c,d]indole

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Chemical Property of 4-[N-(methyl)-N-propargyl]amino-5,5-ethylenedioxy-1-(toluene-4-sulfonyl)-3,4-dihydro-1H-benzo[c,d]indole

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Technology Process of 4-[N-(methyl)-N-propargyl]amino-5,5-ethylenedioxy-1-(toluene-4-sulfonyl)-3,4-dihydro-1H-benzo[c,d]indole

There total 9 articles about 4-[N-(methyl)-N-propargyl]amino-5,5-ethylenedioxy-1-(toluene-4-sulfonyl)-3,4-dihydro-1H-benzo[c,d]indole 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: 66.0%

: 106-96-7
propargyl bromide

: 849413-49-6
4-N-(methyl)amino-5,5-ethylenedioxy-1-(toluene-4-sulfonyl)-3,4-dihydro-1H-benzo[c,d]indole

: 849413-50-9
4-[N-(methyl)-N-propargyl]amino-5,5-ethylenedioxy-1-(toluene-4-sulfonyl)-3,4-dihydro-1H-benzo[c,d]indole

Guidance literature:: With potassium carbonate; In acetone; at 80 ℃; for 12h;
DOI:10.3987/COM-04-S(P)8

Reference yield:

: 41455-40-7
4-amino-5,5-ethylenedioxy-1-(toluene-4-sulfonyl)-3,4-dihydro-1H-benzo[c,d]indole

: 849413-50-9
4-[N-(methyl)-N-propargyl]amino-5,5-ethylenedioxy-1-(toluene-4-sulfonyl)-3,4-dihydro-1H-benzo[c,d]indole

Guidance literature:: Multi-step reaction with 3 steps

1.1: CH₂Cl₂ / 1 h / 50 °C

1.2: 84.2 percent / pyridine / CH₂Cl₂ / 1.5 h / 50 °C

2.1: 63.9 percent / LAH / tetrahydrofuran / 3 h / 55 - 60 °C

3.1: 66 percent / K₂CO₃ / acetone / 12 h / 80 °C

With lithium aluminium tetrahydride; potassium carbonate; In tetrahydrofuran; dichloromethane; acetone;
DOI:10.3987/COM-04-S(P)8

Reference yield:

: 3744-82-9
3,4-dihydrobenzo[cd]indol-5(1H)-one

: 849413-50-9
4-[N-(methyl)-N-propargyl]amino-5,5-ethylenedioxy-1-(toluene-4-sulfonyl)-3,4-dihydro-1H-benzo[c,d]indole

Guidance literature:: Multi-step reaction with 8 steps

1.1: 90.7 percent / Bu₄NHSO₄; KOH / CH₂Cl₂ / 1.5 h / 0 - 20 °C

2.1: 77 percent / Br₂*1,4-dioxane / CCl₄; CHCl₃; diethyl ether / 3 h / 5 - 10 °C

3.1: 88 percent / NaN₃ / dimethylformamide; H₂O; acetic acid / 0.5 h / 5 - 20 °C

4.1: 95 percent / BF₃*OEt₂ / CHCl₃ / 28 h / 20 °C

5.1: 97 percent / LAH / tetrahydrofuran / 0 - 20 °C

6.1: CH₂Cl₂ / 1 h / 50 °C

6.2: 84.2 percent / pyridine / CH₂Cl₂ / 1.5 h / 50 °C

7.1: 63.9 percent / LAH / tetrahydrofuran / 3 h / 55 - 60 °C

8.1: 66 percent / K₂CO₃ / acetone / 12 h / 80 °C

With potassium hydroxide; lithium aluminium tetrahydride; sodium azide; boron trifluoride diethyl etherate; tetra(n-butyl)ammonium hydrogensulfate; dioxane dibromide; potassium carbonate; In tetrahydrofuran; tetrachloromethane; diethyl ether; dichloromethane; chloroform; water; acetic acid; N,N-dimethyl-formamide; acetone;
DOI:10.3987/COM-04-S(P)8