1-(tert-butoxycarbonylamino)-7-(3-fluorophenyl)isoquinoline-4-carboxylic acid

Base Information

Chemical Name:1-(tert-butoxycarbonylamino)-7-(3-fluorophenyl)isoquinoline-4-carboxylic acid
CAS No.:1449278-81-2
Molecular Formula:C₂₁H₁₉FN₂O₄
Molecular Weight:382.391
Hs Code.:

Synonyms:1-(tert-butoxycarbonylamino)-7-(3-fluorophenyl)isoquinoline-4-carboxylic acid

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Chemical Property of 1-(tert-butoxycarbonylamino)-7-(3-fluorophenyl)isoquinoline-4-carboxylic acid

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Technology Process of 1-(tert-butoxycarbonylamino)-7-(3-fluorophenyl)isoquinoline-4-carboxylic acid

There total 7 articles about 1-(tert-butoxycarbonylamino)-7-(3-fluorophenyl)isoquinoline-4-carboxylic acid 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: 52.3%

: methyl 1-(tert-butoxycarbonylamino)-7-(3-fluorophenyl)isoquinoline-4-carboxylate

: 1449278-81-2
1-(tert-butoxycarbonylamino)-7-(3-fluorophenyl)isoquinoline-4-carboxylic acid

Guidance literature:: With sodium hydroxide; In tetrahydrofuran; methanol; water; at 20 ℃;
DOI:10.1021/acsmedchemlett.5b00174

Reference yield:

: 215453-51-3
7-bromo-1-chloroisoquinoline

: 1449278-81-2
1-(tert-butoxycarbonylamino)-7-(3-fluorophenyl)isoquinoline-4-carboxylic acid

Guidance literature:: Multi-step reaction with 6 steps

1: ammonium hydroxide; 1-methyl-pyrrolidin-2-one / water / 20 h / 148 °C / Sealed tube

2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / water; 1,4-dioxane / 15 h / Inert atmosphere; Reflux

3: N-Bromosuccinimide / N,N-dimethyl-formamide / 3 h / 0 °C / Inert atmosphere

4: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; dmap / 70 °C / 2585.81 Torr

5: dmap; triethylamine / dichloromethane / 48 h / 20 °C / Inert atmosphere

6: sodium hydroxide / water; methanol; tetrahydrofuran / 20 °C

With 1-methyl-pyrrolidin-2-one; dmap; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; ammonium hydroxide; N-Bromosuccinimide; sodium carbonate; triethylamine; sodium hydroxide; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1021/acsmedchemlett.5b00174

Reference yield:

: 223671-15-6
7-bromo-1-hydroxyisoquinoline

: 1449278-81-2
1-(tert-butoxycarbonylamino)-7-(3-fluorophenyl)isoquinoline-4-carboxylic acid

Guidance literature:: Multi-step reaction with 7 steps

1: trichlorophosphate / 3 h / 100 °C / Inert atmosphere

2: ammonium hydroxide; 1-methyl-pyrrolidin-2-one / water / 20 h / 148 °C / Sealed tube

3: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / water; 1,4-dioxane / 15 h / Inert atmosphere; Reflux

4: N-Bromosuccinimide / N,N-dimethyl-formamide / 3 h / 0 °C / Inert atmosphere

5: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; dmap / 70 °C / 2585.81 Torr

6: dmap; triethylamine / dichloromethane / 48 h / 20 °C / Inert atmosphere

7: sodium hydroxide / water; methanol; tetrahydrofuran / 20 °C

With 1-methyl-pyrrolidin-2-one; dmap; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; ammonium hydroxide; N-Bromosuccinimide; sodium carbonate; triethylamine; sodium hydroxide; trichlorophosphate; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1021/acsmedchemlett.5b00174