7-benzyloxy-4-[2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-indole

Base Information

Chemical Name:7-benzyloxy-4-[2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-indole
CAS No.:476622-86-3
Molecular Formula:C₃₆H₅₈BNO₅Si₂
Molecular Weight:651.842
Hs Code.:

7-benzyloxy-4-[2-(<i>tert</i>-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1-(2-trimethylsilanyl-ethoxymethyl)-1<i>H</i>-indole

Synonyms:7-benzyloxy-4-[2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-indole

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Chemical Property of 7-benzyloxy-4-[2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-indole

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Technology Process of 7-benzyloxy-4-[2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-indole

There total 7 articles about 7-benzyloxy-4-[2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-indole 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: 73.0%

: 61676-62-8
2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

: 476623-33-3
7-benzyloxy-3-bromo-4-[2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-1-(2-trimethylsilanyl-ethoxymethyl)-1H-indole

: 476622-86-3
7-benzyloxy-4-[2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-indole

Guidance literature:: 7-benzyloxy-3-bromo-4-[2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-1-(2-trimethylsilanyl-ethoxymethyl)-1H-indole; With tert.-butyl lithium; In tetrahydrofuran; pentane; at -78 ℃; for 0.25h;

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane; In tetrahydrofuran; pentane; at -78 ℃; for 1h; Further stages.;
DOI:10.1021/ja027822b

Reference yield:

: 383868-64-2
1-(benzyloxy)-4-bromo-2-nitrobenzene

: 476622-86-3
7-benzyloxy-4-[2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-indole

Guidance literature:: Multi-step reaction with 7 steps

1.1: tetrahydrofuran / 4 h / -40 °C

2.1: sodium hydride / tetrahydrofuran / 0.5 h / 23 °C

2.2: 13 / 6 h / 23 °C

3.1: tert.-butyl lithium / tetrahydrofuran; pentane / 0.25 h / -78 °C

3.2: 13; 17 / 1.5 h / -78 °C

4.1: sodium carbonate / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / methanol; benzene / 2 h / 80 °C

5.1: hydrogen / palladium / benzene / 1 h / 760.05 Torr

6.1: N-Bromosuccinimide / tetrahydrofuran / 0.08 h

7.1: tert.-butyl lithium / tetrahydrofuran; pentane / 0.25 h / -78 °C

7.2: 13; 17 / 1 h / -78 °C

With N-Bromosuccinimide; hydrogen; tert.-butyl lithium; sodium hydride; sodium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; palladium; In tetrahydrofuran; methanol; pentane; benzene; 4.1: Suzuki coupling;
DOI:10.1021/ja027822b

Reference yield:

: 476622-92-1
7-benzyloxy-4-bromoindole

: 476622-86-3
7-benzyloxy-4-[2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-indole

Guidance literature:: Multi-step reaction with 6 steps

1.1: sodium hydride / tetrahydrofuran / 0.5 h / 23 °C

1.2: 13 / 6 h / 23 °C

2.1: tert.-butyl lithium / tetrahydrofuran; pentane / 0.25 h / -78 °C

2.2: 13; 17 / 1.5 h / -78 °C

3.1: sodium carbonate / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / methanol; benzene / 2 h / 80 °C

4.1: hydrogen / palladium / benzene / 1 h / 760.05 Torr

5.1: N-Bromosuccinimide / tetrahydrofuran / 0.08 h

6.1: tert.-butyl lithium / tetrahydrofuran; pentane / 0.25 h / -78 °C

6.2: 13; 17 / 1 h / -78 °C

With N-Bromosuccinimide; hydrogen; tert.-butyl lithium; sodium hydride; sodium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; palladium; In tetrahydrofuran; methanol; pentane; benzene; 3.1: Suzuki coupling;
DOI:10.1021/ja027822b