7-benzyloxy-4-[1-(tert-butyl-dimethyl-silanyloxymethyl)-vinyl]-1-(2-trimethylsilanyl-ethoxymethyl)-1H-indole

Base Information

• Chemical Name: 7-benzyloxy-4-[1-(tert-butyl-dimethyl-silanyloxymethyl)-vinyl]-1-(2-trimethylsilanyl-ethoxymethyl)-1H-indole
• CAS No.: 476623-04-8
• Molecular Formula: C₃₀H₄₅NO₃Si₂
• Molecular Weight: 523.863
• Mol file: 476623-04-8.mol

Synonyms:7-benzyloxy-4-[1-(tert-butyl-dimethyl-silanyloxymethyl)-vinyl]-1-(2-trimethylsilanyl-ethoxymethyl)-1H-indole

Chemical Property of 7-benzyloxy-4-[1-(tert-butyl-dimethyl-silanyloxymethyl)-vinyl]-1-(2-trimethylsilanyl-ethoxymethyl)-1H-indole

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 7-benzyloxy-4-[1-(tert-butyl-dimethyl-silanyloxymethyl)-vinyl]-1-(2-trimethylsilanyl-ethoxymethyl)-1H-indole

There total 4 articles about 7-benzyloxy-4-[1-(tert-butyl-dimethyl-silanyloxymethyl)-vinyl]-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: 83.0%

[(2-bromo-2-propen-1-yl)oxy](dimethyl)(2-methyl-2-propanyl)silane (293313-66-3) + 7-benzyloxy-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-indole (476623-00-4) → 7-benzyloxy-4-[1-(tert-butyl-dimethyl-silanyloxymethyl)-vinyl]-1-(2-trimethylsilanyl-ethoxymethyl)-1H-indole (476623-04-8)

Guidance literature:

With sodium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In methanol; benzene; at 80 ℃; for 2h;

DOI:10.1021/ja027822b

Reference yield:

1-(benzyloxy)-4-bromo-2-nitrobenzene (383868-64-2) → 7-benzyloxy-4-[1-(tert-butyl-dimethyl-silanyloxymethyl)-vinyl]-1-(2-trimethylsilanyl-ethoxymethyl)-1H-indole (476623-04-8)

Guidance literature:

Multi-step reaction with 4 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

With tert.-butyl lithium; sodium hydride; sodium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; pentane; benzene; 4.1: Suzuki coupling;

DOI:10.1021/ja027822b

Reference yield:

7-benzyloxy-4-bromoindole (476622-92-1) → 7-benzyloxy-4-[1-(tert-butyl-dimethyl-silanyloxymethyl)-vinyl]-1-(2-trimethylsilanyl-ethoxymethyl)-1H-indole (476623-04-8)

Guidance literature:

Multi-step reaction with 3 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

With tert.-butyl lithium; sodium hydride; sodium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; pentane; benzene; 3.1: Suzuki coupling;

DOI:10.1021/ja027822b

upstream raw materials:

[(2-bromo-2-propen-1-yl)oxy](dimethyl)(2-methyl-2-propanyl)silane

7-benzyloxy-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-indole

1-(benzyloxy)-4-bromo-2-nitrobenzene

7-benzyloxy-4-bromoindole

Downstream raw materials:

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

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

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

3-{7-benzyloxy-3-[5-(6-bromo-1H-indol-3-yl)-6-methoxy-pyrazin-2-yl]-1H-indol-4-yl}-1-nitro-butan-2-one