3-(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)-5-{3-[(methylamino)methyl] phenyl}-1H-indole-7-carboxamide

Base Information

Chemical Name:3-(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)-5-{3-[(methylamino)methyl] phenyl}-1H-indole-7-carboxamide
CAS No.:1065177-32-3
Molecular Formula:C₂₂H₂₅N₃O₃S
Molecular Weight:411.525
Hs Code.:

Synonyms:3-(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)-5-{3-[(methylamino)methyl] phenyl}-1H-indole-7-carboxamide

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Chemical Property of 3-(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)-5-{3-[(methylamino)methyl] phenyl}-1H-indole-7-carboxamide

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Technology Process of 3-(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)-5-{3-[(methylamino)methyl] phenyl}-1H-indole-7-carboxamide

There total 12 articles about 3-(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)-5-{3-[(methylamino)methyl] phenyl}-1H-indole-7-carboxamide 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: 13.85%

: 1065184-15-7
3-(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)-5-(3-formylphenyl)-1H-indole-7-carboxamide

: 593-51-1
methylamine hydrochloride

: 1065177-32-3
3-(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)-5-{3-[(methylamino)methyl] phenyl}-1H-indole-7-carboxamide

Guidance literature:: 3-(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)-5-(3-formylphenyl)-1H-indole-7-carboxamide; methylamine hydrochloride; With acetic acid; In methanol; dimethyl sulfoxide; at 20 ℃; for 1h;

With sodium cyanoborohydride; In methanol; dimethyl sulfoxide; for 0.75h;

Reference yield:

: 1065181-79-4
5-bromo-3-(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)-1H-indole-7-carboxylic acid

: 1065177-32-3
3-(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)-5-{3-[(methylamino)methyl] phenyl}-1H-indole-7-carboxamide

Guidance literature:: Multi-step reaction with 3 steps

1.1: ammonia; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / 1,4-dioxane; N,N-dimethyl-formamide / 0.33 h / 100 °C / Inert atmosphere; Microwave irradiation; Sealed

2.1: potassium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane; water / 0.08 h / 100 °C / Microwave irradiation

3.1: acetic acid / methanol; dimethyl sulfoxide / 1 h / 20 °C

3.2: 0.75 h

With ammonia; potassium carbonate; benzotriazol-1-ol; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; methanol; water; dimethyl sulfoxide; N,N-dimethyl-formamide;

Reference yield:

: 496-15-1
1-indoline

: 1065177-32-3
3-(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)-5-{3-[(methylamino)methyl] phenyl}-1H-indole-7-carboxamide

Guidance literature:: Multi-step reaction with 12 steps

1.1: sodium hydroxide / dichloromethane; water / 20 °C / Inert atmosphere

2.1: N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium / diethyl ether; cyclohexane / 1.67 h / -78 °C / Inert atmosphere; Cooling with acetone-dry ice

2.2: 1 h / -78 - 20 °C / Inert atmosphere

3.1: N-Bromosuccinimide / dichloromethane / 20 °C / Inert atmosphere

4.1: trifluoroacetic acid / 16 h / 20 °C / Inert atmosphere

5.1: manganese(IV) oxide / tetrahydrofuran / 20 °C / Inert atmosphere

6.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 0 °C / Inert atmosphere

6.2: 15 h / 20 °C / Inert atmosphere

7.1: dmap / tetrahydrofuran; acetonitrile / 4.5 h / 20 °C / Inert atmosphere

8.1: urea hydrogen peroxide adduct; trifluoroacetic anhydride / acetonitrile / 0 - 20 °C / Inert atmosphere

9.1: sodium hydroxide / methanol; water / 1.5 h / 85 °C / Inert atmosphere; Reflux

9.2: pH 1

10.1: ammonia; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / 1,4-dioxane; N,N-dimethyl-formamide / 0.33 h / 100 °C / Inert atmosphere; Microwave irradiation; Sealed

11.1: potassium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane; water / 0.08 h / 100 °C / Microwave irradiation

12.1: acetic acid / methanol; dimethyl sulfoxide / 1 h / 20 °C

12.2: 0.75 h

With dmap; manganese(IV) oxide; N-Bromosuccinimide; N,N,N,N,-tetramethylethylenediamine; trimethylsilyl trifluoromethanesulfonate; ammonia; sec.-butyllithium; urea hydrogen peroxide adduct; potassium carbonate; benzotriazol-1-ol; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trifluoroacetic acid; trifluoroacetic anhydride; sodium hydroxide; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; dichloromethane; cyclohexane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetonitrile;