N-pivaloyl-4-bromoindole

Base Information

• Chemical Name: N-pivaloyl-4-bromoindole
• CAS No.: 1196981-04-0
• Molecular Formula: C₁₃H₁₄BrNO
• Molecular Weight: 280.164
• Mol file: 1196981-04-0.mol

Synonyms:1-(4-bromo-1H-indol-1-yl)-2,2-dimethylpropan-1-one

Chemical Property of N-pivaloyl-4-bromoindole

Chemical Property:

• Melting Point: 61-63 °C
• Boiling Point: 344.5±15.0 °C(Predicted)
• Density: 1.34±0.1 g/cm3(Predicted)

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of N-pivaloyl-4-bromoindole

There total 1 articles about N-pivaloyl-4-bromoindole 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: 89.0%

4-bromo-1H-indole (52488-36-5) + pivaloyl chloride (3282-30-2) → 1-(4-bromo-1H-indol-1-yl)-2,2-dimethylpropan-1-one (1196981-04-0)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 0 - 20 ℃; Inert atmosphere;

DOI:10.1021/ol902304n

Reference yield: 97.0%

4-toluenesulfonyl azide (941-55-9) + 1-(4-bromo-1H-indol-1-yl)-2,2-dimethylpropan-1-one (1196981-04-0) → N-(4-bromo-1-pivaloyl-1H-indol-7-yl)-4-methylbenzenesulfonamide

Guidance literature:

With [Cp*Ir(OCOCH₃)₂]; silver(I) triflimide; In 1,2-dichloro-ethane; at 25 ℃; for 12h; regioselective reaction;

DOI:10.1021/acs.orglett.6b00662

Reference yield: 95.0%

1-(4-bromo-1H-indol-1-yl)-2,2-dimethylpropan-1-one (1196981-04-0) + Methyl phenyldiazoacetate (22979-35-7) → methyl 6-bromo-1-phenyl-2-pivaloyl-1,1a,2,6b-tetrahydrocyclopropa[b]indole-1-carboxylate

Guidance literature:

In dichloromethane; at 20 ℃; for 6h; diastereoselective reaction; Schlenk technique; Irradiation; Green chemistry;

DOI:10.1055/s-0037-1610668

upstream raw materials:

4-bromo-1H-indole

pivaloyl chloride

Downstream raw materials:

3-(2'-chloro-5'-nitrophenyl)-4-bromo-N-pivaloylindole

4-bromo-1H-indole

Refernces

• 1、 Iqbal, Saqib A.,Cid, Jessica,Procter, Richard J.,Uzelac, Marina,Yuan, Kang,Ingleson, Michael J.. "Acyl-Directed ortho-Borylation of Anilines and C7 Borylation of Indoles using just BBr3". supporting information. p. 15381 - 15385. Retrieved 2019/10/22.
• 2、 Ruiz, Míriam,Sánchez, J. Domingo,López-Alvarado, Pilar,Menéndez, J. Carlos. "A systematic study of two complementary protocols allowing the general, mild and efficient deprotection of N-pivaloylindoles". experimental part. p. 705 - 710. Retrieved 2012/01/06.