tert-butyl 6-(5-(3-cyano-4-isopropoxyphenyl)-1,3,4-thiadiazol-2-yl)-5-methyl-3,4-dihydroisoquinoline-2(1H)-carboxylate

Base Information

Chemical Name:tert-butyl 6-(5-(3-cyano-4-isopropoxyphenyl)-1,3,4-thiadiazol-2-yl)-5-methyl-3,4-dihydroisoquinoline-2(1H)-carboxylate
CAS No.:1258440-72-0
Molecular Formula:C₂₇H₃₀N₄O₃S
Molecular Weight:490.626
Hs Code.:

Synonyms:tert-butyl 6-(5-(3-cyano-4-isopropoxyphenyl)-1,3,4-thiadiazol-2-yl)-5-methyl-3,4-dihydroisoquinoline-2(1H)-carboxylate

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Chemical Property of tert-butyl 6-(5-(3-cyano-4-isopropoxyphenyl)-1,3,4-thiadiazol-2-yl)-5-methyl-3,4-dihydroisoquinoline-2(1H)-carboxylate

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Technology Process of tert-butyl 6-(5-(3-cyano-4-isopropoxyphenyl)-1,3,4-thiadiazol-2-yl)-5-methyl-3,4-dihydroisoquinoline-2(1H)-carboxylate

There total 15 articles about tert-butyl 6-(5-(3-cyano-4-isopropoxyphenyl)-1,3,4-thiadiazol-2-yl)-5-methyl-3,4-dihydroisoquinoline-2(1H)-carboxylate 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: 71.0%

: 5-(5-bromo-1,3,4-thiadiazol-2-yl)-2-[(1-methylethyl)oxy]-benzonitrile

: 1258440-71-9
tert-butyl 5-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydroisoquinoline-2(1H)-carboxylate

: 1258440-72-0
tert-butyl 6-(5-(3-cyano-4-isopropoxyphenyl)-1,3,4-thiadiazol-2-yl)-5-methyl-3,4-dihydroisoquinoline-2(1H)-carboxylate

Guidance literature:: With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; sodium carbonate; In 1,2-dimethoxyethane; water; for 3h; Inert atmosphere; Reflux;
DOI:10.1021/acs.jmedchem.5b01102

Reference yield:

: 1165923-89-6
1,1-dimethylethyl 6-hydroxy-5-methyl-3,4-dihydro-2(1H)-isoquinolinecarboxylate

: 1258440-72-0
tert-butyl 6-(5-(3-cyano-4-isopropoxyphenyl)-1,3,4-thiadiazol-2-yl)-5-methyl-3,4-dihydroisoquinoline-2(1H)-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1: pyridine / dichloromethane / -30 - 20 °C / Inert atmosphere

2: potassium acetate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / Reflux

3: sodium carbonate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / 1,2-dimethoxyethane; water / 6 h / Inert atmosphere

With pyridine; potassium acetate; sodium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; In 1,4-dioxane; 1,2-dimethoxyethane; dichloromethane; water;

Reference yield:

: 258273-31-3
3-cyano-4-isopropoxybenzoic acid

: 1258440-72-0
tert-butyl 6-(5-(3-cyano-4-isopropoxyphenyl)-1,3,4-thiadiazol-2-yl)-5-methyl-3,4-dihydroisoquinoline-2(1H)-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1.1: trichlorophosphate / 3 h / 90 °C

1.2: 35 °C / pH 10 / Cooling with ice

2.1: copper(ll) bromide; tert.-butylnitrite / acetonitrile / 20 - 70 °C

3.1: sodium carbonate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / 1,2-dimethoxyethane; water / 6 h / Inert atmosphere

With tert.-butylnitrite; sodium carbonate; copper(ll) bromide; trichlorophosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; In 1,2-dimethoxyethane; water; acetonitrile;