3-iodo-1-(phenylsulfonyl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole

Base Information

• Chemical Name: 3-iodo-1-(phenylsulfonyl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole
• CAS No.: 857934-94-2
• Molecular Formula: C₂₀H₂₁BINO₄S
• Molecular Weight: 509.173
• Mol file: 857934-94-2.mol

Synonyms:3-iodo-1-(phenylsulfonyl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole

Chemical Property of 3-iodo-1-(phenylsulfonyl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-iodo-1-(phenylsulfonyl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole

There total 2 articles about 3-iodo-1-(phenylsulfonyl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-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: 76.0%

2-methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1195-66-0) + isopropylmagnesium chloride (1068-55-9) + 2,3-diiodo-1-(phenylsulfonyl)-1H-indole (80360-26-5) → 3-iodo-1-(phenylsulfonyl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (857934-94-2)

Guidance literature:

With ammonium chloride; In tetrahydrofuran; iPrMgCl in THF added to soln. at -78°C of C8H4NI2(SO2C6H5) in THFin dry, argon-flushed Schlenk tube; mixt. stirred for 2 h, until I/Mg e xchange; BO2(C(CH3)2)2(OCH3) added; allowed to warm to room. temp., 1 h;quenched with aq. soln. of NH4Cl; extrn. with Et2O; dried over Na2SO4; filtration, soln. evapd. in vac.; recrystn. from CH2Cl2;

DOI:10.1002/anie.200462928

Reference yield:

2,3-dimethyl-2,3-butane diol (76-09-5) → 3-iodo-1-(phenylsulfonyl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (857934-94-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 68 percent / 2 h / 68 °C

2.1: iPrMgCl*LiCl / tetrahydrofuran / 2 h / -78 °C

2.2: 76 percent / tetrahydrofuran / -78 - 20 °C

With TurboGrignard; In tetrahydrofuran;

DOI:10.1002/anie.200462928

Reference yield: 81.0%

3-iodo-1-(phenylsulfonyl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (857934-94-2) + propionyl chloride (79-03-8) → 1-[1-(phenylsulfonyl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indol-3-yl]propan-1-one

Guidance literature:

3-iodo-1-(phenylsulfonyl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole; With TurboGrignard; In tetrahydrofuran; at -78 ℃; for 1h;

In tetrahydrofuran; at -78 ℃; for 0.333333h;

propionyl chloride; In tetrahydrofuran; at -78 - 20 ℃;

DOI:10.1002/anie.200462928

upstream raw materials:

2,3-dimethyl-2,3-butane diol

2-methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

isopropylmagnesium chloride

2,3-diiodo-1-(phenylsulfonyl)-1H-indole

Refernces