tert-butyl 7-(4-bromophenyl)-6-methoxyindoline-1-carboxylate

Base Information

• Chemical Name: tert-butyl 7-(4-bromophenyl)-6-methoxyindoline-1-carboxylate
• CAS No.: 1428963-61-4
• Molecular Formula: C₂₀H₂₂BrNO₃
• Molecular Weight: 404.304
• Mol file: 1428963-61-4.mol

Synonyms:tert-butyl 7-(4-bromophenyl)-6-methoxyindoline-1-carboxylate

Chemical Property of tert-butyl 7-(4-bromophenyl)-6-methoxyindoline-1-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl 7-(4-bromophenyl)-6-methoxyindoline-1-carboxylate

There total 11 articles about tert-butyl 7-(4-bromophenyl)-6-methoxyindoline-1-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:

1,4-bromoiodobenzene (589-87-7) + C14H18CuNO3 → tert-butyl 7-(4-bromophenyl)-6-methoxyindoline-1-carboxylate (1428963-61-4)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; at -78 - 20 ℃; for 3h;

DOI:10.1021/ol400597f

Reference yield:

4-nitro-phenol (100-02-7,78813-13-5,89830-32-0) → tert-butyl 7-(4-bromophenyl)-6-methoxyindoline-1-carboxylate (1428963-61-4)

Guidance literature:

Multi-step reaction with 9 steps

1.1: triethylamine / dichloromethane / 0.75 h / 0 - 20 °C

2.1: palladium 10% on activated carbon; hydrogen / ethyl acetate; ethanol / 3 h / 20 °C / 51683.5 Torr

3.1: N-Bromosuccinimide / N,N-dimethyl-formamide / 0.5 h / 0 - 20 °C

4.1: sulfuric acid / water; acetonitrile / 0.17 h / 0 °C

4.2: 1.5 h / 0 - 5 °C

4.3: 0.25 h / 0 °C

5.1: potassium hydroxide / methanol; dichloromethane / 1 h / 20 °C / Inert atmosphere

6.1: potassium carbonate / acetone / 16 h / Reflux

7.1: isopropylmagnesium chloride / toluene; diethyl ether / 1 h / -40 °C

7.2: 0.25 h / -40 °C

7.3: 0.58 h / -40 - 0 °C

8.1: bis(2,2,6,6-tetramethylpiperidin-1-yl)magnesium-bis(lithium chloride) complex / tetrahydrofuran / 1 h / -78 - 0 °C

8.2: 1 h / -78 °C

9.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / tetrahydrofuran / 3 h / -78 - 20 °C

With N-Bromosuccinimide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; bis(2,2,6,6-tetramethylpiperidin-1-yl)magnesium-bis(lithium chloride) complex; sulfuric acid; palladium 10% on activated carbon; hydrogen; isopropylmagnesium chloride; potassium carbonate; triethylamine; potassium hydroxide; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetone; toluene; acetonitrile;

DOI:10.1021/ol400597f

Reference yield:

methanesulfonic acid 4-aminophenyl ester (24690-19-5) → tert-butyl 7-(4-bromophenyl)-6-methoxyindoline-1-carboxylate (1428963-61-4)

Guidance literature:

Multi-step reaction with 7 steps

1.1: N-Bromosuccinimide / N,N-dimethyl-formamide / 0.5 h / 0 - 20 °C

2.1: sulfuric acid / water; acetonitrile / 0.17 h / 0 °C

2.2: 1.5 h / 0 - 5 °C

2.3: 0.25 h / 0 °C

3.1: potassium hydroxide / methanol; dichloromethane / 1 h / 20 °C / Inert atmosphere

4.1: potassium carbonate / acetone / 16 h / Reflux

5.1: isopropylmagnesium chloride / toluene; diethyl ether / 1 h / -40 °C

5.2: 0.25 h / -40 °C

5.3: 0.58 h / -40 - 0 °C

6.1: bis(2,2,6,6-tetramethylpiperidin-1-yl)magnesium-bis(lithium chloride) complex / tetrahydrofuran / 1 h / -78 - 0 °C

6.2: 1 h / -78 °C

7.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / tetrahydrofuran / 3 h / -78 - 20 °C

With N-Bromosuccinimide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; bis(2,2,6,6-tetramethylpiperidin-1-yl)magnesium-bis(lithium chloride) complex; sulfuric acid; isopropylmagnesium chloride; potassium carbonate; potassium hydroxide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; acetonitrile;

DOI:10.1021/ol400597f

upstream raw materials:

4-nitro-phenol

p-nitrophenyl methanesulfonate

methanesulfonic acid 4-aminophenyl ester

4-amino-3-bromophenyl methanesulfonate