tert-butyl 2-(2-bromophenyl)-3-oxo-2-{3-[(trimethylsilyl)oxy]but-3-enyl}indoline-1-carboxylate

Base Information

Chemical Name:tert-butyl 2-(2-bromophenyl)-3-oxo-2-{3-[(trimethylsilyl)oxy]but-3-enyl}indoline-1-carboxylate
CAS No.:524712-16-1
Molecular Formula:C₂₆H₃₂BrNO₄Si
Molecular Weight:530.534
Hs Code.:

Synonyms:tert-butyl 2-(2-bromophenyl)-3-oxo-2-{3-[(trimethylsilyl)oxy]but-3-enyl}indoline-1-carboxylate

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Chemical Property of tert-butyl 2-(2-bromophenyl)-3-oxo-2-{3-[(trimethylsilyl)oxy]but-3-enyl}indoline-1-carboxylate

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Technology Process of tert-butyl 2-(2-bromophenyl)-3-oxo-2-{3-[(trimethylsilyl)oxy]but-3-enyl}indoline-1-carboxylate

There total 11 articles about tert-butyl 2-(2-bromophenyl)-3-oxo-2-{3-[(trimethylsilyl)oxy]but-3-enyl}indoline-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: 78.0%

: 75-77-4
chloro-trimethyl-silane

: 524712-14-9
tert-butyl 2-(2-bromophenyl)-3-oxo-2-(3-oxobutyl)indoline-1-carboxylate

: 524712-16-1
tert-butyl 2-(2-bromophenyl)-3-oxo-2-{3-[(trimethylsilyl)oxy]but-3-enyl}indoline-1-carboxylate

Guidance literature:: tert-butyl 2-(2-bromophenyl)-3-oxo-2-(3-oxobutyl)indoline-1-carboxylate; With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃; for 0.0833333h;

chloro-trimethyl-silane; In tetrahydrofuran; at -78 - 20 ℃;
DOI:10.1021/ja021380m

Reference yield:

: 88207-45-8
2-(2'-bromophenyl)-1H-indole

: 524712-16-1
tert-butyl 2-(2-bromophenyl)-3-oxo-2-{3-[(trimethylsilyl)oxy]but-3-enyl}indoline-1-carboxylate

Guidance literature:: Multi-step reaction with 8 steps

1.1: 97 percent / NaNO₂ / acetic acid / 3 h / 20 °C

2.1: 94 percent / Na₂S₂O₄; NaOH / ethanol / 24 h / Heating

3.1: 98 percent / PbO₂ / benzene / 24 h / Heating

4.1: 56 percent / aq. HCl / toluene / 12 h / 20 °C

5.1: 88 percent / tetrahydrofuran / 1 h / 20 °C

6.1: 89 percent / HCOOH / toluene / 0.5 h / Heating

7.1: 96 percent / 4-(dimethylamino)pyridine / acetonitrile / 17 h / 20 °C

8.1: lithium diisopropylamide / tetrahydrofuran / 0.08 h / -78 °C

8.2: 78 percent / tetrahydrofuran / -78 - 20 °C

With hydrogenchloride; dmap; sodium hydroxide; formic acid; sodium dithionite; lead dioxide; lithium diisopropyl amide; sodium nitrite; In tetrahydrofuran; ethanol; acetic acid; toluene; acetonitrile; benzene;
DOI:10.1021/ja021380m

Reference yield:

: 2142-69-0
2-bromophenyl methyl ketone

: 524712-16-1
tert-butyl 2-(2-bromophenyl)-3-oxo-2-{3-[(trimethylsilyl)oxy]but-3-enyl}indoline-1-carboxylate

Guidance literature:: Multi-step reaction with 9 steps

1.1: 78 percent / polyphosphoric acid / 4 h / 100 - 110 °C

2.1: 97 percent / NaNO₂ / acetic acid / 3 h / 20 °C

3.1: 94 percent / Na₂S₂O₄; NaOH / ethanol / 24 h / Heating

4.1: 98 percent / PbO₂ / benzene / 24 h / Heating

5.1: 56 percent / aq. HCl / toluene / 12 h / 20 °C

6.1: 88 percent / tetrahydrofuran / 1 h / 20 °C

7.1: 89 percent / HCOOH / toluene / 0.5 h / Heating

8.1: 96 percent / 4-(dimethylamino)pyridine / acetonitrile / 17 h / 20 °C

9.1: lithium diisopropylamide / tetrahydrofuran / 0.08 h / -78 °C

9.2: 78 percent / tetrahydrofuran / -78 - 20 °C

With hydrogenchloride; dmap; sodium hydroxide; formic acid; sodium dithionite; PPA; lead dioxide; lithium diisopropyl amide; sodium nitrite; In tetrahydrofuran; ethanol; acetic acid; toluene; acetonitrile; benzene; 1.1: Fischer indole synthesis;
DOI:10.1021/ja021380m