5-(4-bromo-2-fluoro-6-methoxyphenyl)-N-methyl-N-(2,2,6,6-tetramethylpiperidin-4-yl)-1,3,4-thiadiazol-2-amine

Base Information

Chemical Name:5-(4-bromo-2-fluoro-6-methoxyphenyl)-N-methyl-N-(2,2,6,6-tetramethylpiperidin-4-yl)-1,3,4-thiadiazol-2-amine
CAS No.:1620515-97-0
Molecular Formula:C₁₉H₂₆BrFN₄OS
Molecular Weight:457.41
Hs Code.:

Synonyms:5-(4-bromo-2-fluoro-6-methoxyphenyl)-N-methyl-N-(2,2,6,6-tetramethylpiperidin-4-yl)-1,3,4-thiadiazol-2-amine

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Chemical Property of 5-(4-bromo-2-fluoro-6-methoxyphenyl)-N-methyl-N-(2,2,6,6-tetramethylpiperidin-4-yl)-1,3,4-thiadiazol-2-amine

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Technology Process of 5-(4-bromo-2-fluoro-6-methoxyphenyl)-N-methyl-N-(2,2,6,6-tetramethylpiperidin-4-yl)-1,3,4-thiadiazol-2-amine

There total 8 articles about 5-(4-bromo-2-fluoro-6-methoxyphenyl)-N-methyl-N-(2,2,6,6-tetramethylpiperidin-4-yl)-1,3,4-thiadiazol-2-amine 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:

: 1620515-96-9
5-(2-fluoro-6-methoxyphenyl)-N-methyl-N-(2,2,6,6-tetramethylpiperidin-4-yl)-1,3,4-thiadiazol-2-amine

: 1620515-97-0
5-(4-bromo-2-fluoro-6-methoxyphenyl)-N-methyl-N-(2,2,6,6-tetramethylpiperidin-4-yl)-1,3,4-thiadiazol-2-amine

Guidance literature:: 5-(2-fluoro-6-methoxyphenyl)-N-methyl-N-(2,2,6,6-tetramethylpiperidin-4-yl)-1,3,4-thiadiazol-2-amine; With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; bis(pinacol)diborane; 4,4'-di-tert-butyl-2,2'-bipyridine; In 1,4-dioxane; water; at 90 ℃; for 16h; Inert atmosphere;

With copper(ll) bromide; In 1,4-dioxane; methanol; water; at 80 ℃; for 18h;

Reference yield:

: 1620515-96-9
5-(2-fluoro-6-methoxyphenyl)-N-methyl-N-(2,2,6,6-tetramethylpiperidin-4-yl)-1,3,4-thiadiazol-2-amine

: 1620515-97-0
5-(4-bromo-2-fluoro-6-methoxyphenyl)-N-methyl-N-(2,2,6,6-tetramethylpiperidin-4-yl)-1,3,4-thiadiazol-2-amine

: 5-(3-bromo-2-fluoro-6-methoxyphenyl)-N-methyl-N-(2,2,6,6-tetramethylpiperidin-4-yl)-1,3,4-thiadiazol-2-amine

Guidance literature:: 5-(2-fluoro-6-methoxyphenyl)-N-methyl-N-(2,2,6,6-tetramethylpiperidin-4-yl)-1,3,4-thiadiazol-2-amine; With bis(pinacol)diborane; In 1,4-dioxane; for 0.166667h; Inert atmosphere;

With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 4,4'-di-tert-butyl-2,2'-bipyridine; In 1,4-dioxane; at 90 ℃; for 18h; Inert atmosphere;

With copper(ll) bromide; In methanol; water; at 80 ℃; for 18h; Overall yield = 59 percent; Overall yield = 87 mg;
DOI:10.1021/acs.jmedchem.0c02173

Reference yield:

: 137654-21-8
2-fluoro-6-methoxybenzoic acid

: 1620515-97-0
5-(4-bromo-2-fluoro-6-methoxyphenyl)-N-methyl-N-(2,2,6,6-tetramethylpiperidin-4-yl)-1,3,4-thiadiazol-2-amine

Guidance literature:: Multi-step reaction with 4 steps

1.1: trichlorophosphate / 20.5 h / 78 °C / Cooling with ice; Inert atmosphere; Sonication

2.1: tert.-butylnitrite; copper(ll) bromide / acetonitrile / 18 h / 20 °C / Inert atmosphere

3.1: 1-methyl-pyrrolidin-2-one / 18 h / 120 °C

4.1: bis(pinacol)diborane; (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 4,4'-di-tert-butyl-2,2'-bipyridine / water; 1,4-dioxane / 16 h / 90 °C / Inert atmosphere

4.2: 18 h / 80 °C

With tert.-butylnitrite; (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; bis(pinacol)diborane; 4,4'-di-tert-butyl-2,2'-bipyridine; copper(ll) bromide; trichlorophosphate; In 1,4-dioxane; 1-methyl-pyrrolidin-2-one; water; acetonitrile;