6-{4-[5-cyclopropyl-3-(2,6-dichlorophenyl)isoxazol-4-ylmethoxy]piperidin-1-yl}-1-methyl-1H-indole-3-carboxylic acid methyl ester

Base Information

Chemical Name:6-{4-[5-cyclopropyl-3-(2,6-dichlorophenyl)isoxazol-4-ylmethoxy]piperidin-1-yl}-1-methyl-1H-indole-3-carboxylic acid methyl ester
CAS No.:1103500-82-8
Molecular Formula:C₂₉H₂₉Cl₂N₃O₄
Molecular Weight:554.473
Hs Code.:

Synonyms:6-{4-[5-cyclopropyl-3-(2,6-dichlorophenyl)isoxazol-4-ylmethoxy]piperidin-1-yl}-1-methyl-1H-indole-3-carboxylic acid methyl ester

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Chemical Property of 6-{4-[5-cyclopropyl-3-(2,6-dichlorophenyl)isoxazol-4-ylmethoxy]piperidin-1-yl}-1-methyl-1H-indole-3-carboxylic acid methyl ester

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Technology Process of 6-{4-[5-cyclopropyl-3-(2,6-dichlorophenyl)isoxazol-4-ylmethoxy]piperidin-1-yl}-1-methyl-1H-indole-3-carboxylic acid methyl ester

There total 12 articles about 6-{4-[5-cyclopropyl-3-(2,6-dichlorophenyl)isoxazol-4-ylmethoxy]piperidin-1-yl}-1-methyl-1H-indole-3-carboxylic 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: 43.0%

: 6-bromo-1-methyl-1H-indole-3-carboxylic acid methyl ester

: 1103501-11-6
5-cyclopropyl-3-(2,6-dichlorophenyl)-4-((piperidin-4-yloxy)methyl)isoxazole

: 1103500-82-8
6-{4-[5-cyclopropyl-3-(2,6-dichlorophenyl)isoxazol-4-ylmethoxy]piperidin-1-yl}-1-methyl-1H-indole-3-carboxylic acid methyl ester

Guidance literature:: With copper(l) iodide; potassium carbonate; L-proline; In dimethyl sulfoxide; at 120 ℃; for 16h; Product distribution / selectivity;

Reference yield: 34.0%

: 946426-94-4
4-(bromomethyl)-5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazole

: 1103500-46-4
6-(4-hydroxypiperidin-1-yl)-1-methyl-1H-indole-3-carboxylic acid methyl ester

: 1103500-82-8
6-{4-[5-cyclopropyl-3-(2,6-dichlorophenyl)isoxazol-4-ylmethoxy]piperidin-1-yl}-1-methyl-1H-indole-3-carboxylic acid methyl ester

Guidance literature:: 6-(4-hydroxypiperidin-1-yl)-1-methyl-1H-indole-3-carboxylic acid methyl ester; With 18-crown-6 ether; potassium tert-butylate; In tetrahydrofuran; at 20 ℃; for 0.25h;

4-(bromomethyl)-5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazole; In tetrahydrofuran; at 20 ℃; for 1.5h; Product distribution / selectivity;

Reference yield:

: 946426-88-6
5-cyclopropyl-3-(2,6-dichlorophenyl)isoxazole-4-carboxylic acid methyl ester

: 1103500-82-8
6-{4-[5-cyclopropyl-3-(2,6-dichlorophenyl)isoxazol-4-ylmethoxy]piperidin-1-yl}-1-methyl-1H-indole-3-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: diisobutylaluminium hydride / tetrahydrofuran; toluene / 2 h / 0 - 20 °C

2.1: carbon tetrabromide; triphenylphosphine / dichloromethane / 2 h / 0 - 20 °C

3.1: potassium tert-butylate; 18-crown-6 ether / tetrahydrofuran / 0.33 h / 0 - 20 °C

3.2: 14 h / 20 °C

4.1: trifluoroacetic acid / dichloromethane / 1.5 h / 20 °C / Inert atmosphere; Cooling with ice

5.1: copper(l) iodide; L-proline; potassium carbonate / dimethyl sulfoxide / 16 h / 120 °C / Inert atmosphere

With copper(l) iodide; 18-crown-6 ether; carbon tetrabromide; potassium tert-butylate; diisobutylaluminium hydride; potassium carbonate; triphenylphosphine; trifluoroacetic acid; L-proline; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; toluene;
DOI:10.1021/acs.jmedchem.5b01161