N-(p-Toluenesulfonyl)-4-chloromethyl-7-methoxyindole

Base Information

Chemical Name:N-(p-Toluenesulfonyl)-4-chloromethyl-7-methoxyindole
CAS No.:85598-19-2
Molecular Formula:C₁₇H₁₆ClNO₃S
Molecular Weight:349.838
Hs Code.:

Synonyms:N-(p-Toluenesulfonyl)-4-chloromethyl-7-methoxyindole

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of N-(p-Toluenesulfonyl)-4-chloromethyl-7-methoxyindole

Chemical Property:

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Technology Process of N-(p-Toluenesulfonyl)-4-chloromethyl-7-methoxyindole

There total 10 articles about N-(p-Toluenesulfonyl)-4-chloromethyl-7-methoxyindole 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: 82.0%

: 85598-18-1
N-(p-Toluenesulfonyl)-4-hydroxymethyl-7-methoxyindole

: 85598-19-2
N-(p-Toluenesulfonyl)-4-chloromethyl-7-methoxyindole

Guidance literature:: With tetrachloromethane; Hexamethylphosphorous triamide; In tetrahydrofuran; 1) -40 deg C, 10 min; 2) RT, 70 min;
DOI:10.1002/jhet.5570200132

Reference yield:

: 4920-77-8
3-methyl-2-nitrophenol

: 85598-19-2
N-(p-Toluenesulfonyl)-4-chloromethyl-7-methoxyindole

Guidance literature:: Multi-step reaction with 9 steps

1: 160.5 g / Br₂ / acetic acid; CHCl₃ / 2 h

2: 81.2 g / NaOH / H₂O / Heating

3: 1) NaCN; 2) FeCl₃*6H₂O/conc.HCl / 1) DMF, reflux, 3.25 h; 2) DMF/water

4: 78 percent / dimethylformamide / 15 h / Heating

5: 83 percent / H₂ / 5percent Pd/C / ethyl acetate / 2.5 h / 2947.7 Torr

6: 87 percent / Raney nickel slurry, sodium hypophosphite monohydrate / methanol; acetic acid; pyridine; H₂O / 1.25 h / 30 - 40 °C

7: 83 percent / tetra-n-butylammonium bisulfate/NaOH / CH₂Cl₂ / 0.5 h / 5 - 10 °C

8: 90 percent / NaBH₄/NaOH / H₂O; methanol / 1) 5-10 deg C, 20 min; 2) RT, 40 min

9: 82 percent / hexamethylphosphoroustriamide/CCl₄ / tetrahydrofuran / 1) -40 deg C, 10 min; 2) RT, 70 min

With hydrogenchloride; tetrachloromethane; sodium hydroxide; sodium tetrahydroborate; sodium hypophosphite; Raney nickel slurry; sodium cyanide; hydrogen; bromine; tetra(n-butyl)ammonium hydrogensulfate; Hexamethylphosphorous triamide; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; dichloromethane; chloroform; water; acetic acid; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1002/jhet.5570200132

Reference yield:

: 85598-12-5
4-bromo-3-methyl-2-nitro-phenol

: 85598-19-2
N-(p-Toluenesulfonyl)-4-chloromethyl-7-methoxyindole

Guidance literature:: Multi-step reaction with 8 steps

1: 81.2 g / NaOH / H₂O / Heating

2: 1) NaCN; 2) FeCl₃*6H₂O/conc.HCl / 1) DMF, reflux, 3.25 h; 2) DMF/water

3: 78 percent / dimethylformamide / 15 h / Heating

4: 83 percent / H₂ / 5percent Pd/C / ethyl acetate / 2.5 h / 2947.7 Torr

5: 87 percent / Raney nickel slurry, sodium hypophosphite monohydrate / methanol; acetic acid; pyridine; H₂O / 1.25 h / 30 - 40 °C

6: 83 percent / tetra-n-butylammonium bisulfate/NaOH / CH₂Cl₂ / 0.5 h / 5 - 10 °C

7: 90 percent / NaBH₄/NaOH / H₂O; methanol / 1) 5-10 deg C, 20 min; 2) RT, 40 min

8: 82 percent / hexamethylphosphoroustriamide/CCl₄ / tetrahydrofuran / 1) -40 deg C, 10 min; 2) RT, 70 min

With hydrogenchloride; tetrachloromethane; sodium hydroxide; sodium tetrahydroborate; sodium hypophosphite; Raney nickel slurry; sodium cyanide; hydrogen; tetra(n-butyl)ammonium hydrogensulfate; Hexamethylphosphorous triamide; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; dichloromethane; water; acetic acid; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1002/jhet.5570200132