7-(4,4,5,5 TETRAMETHYL 1,3,2 DIOXABOROLAN-2-YL)-1,2,3,4-TETRAHYDROCYCLO-PENT[B]INDOLE

Base Information

• Chemical Name: 7-(4,4,5,5 TETRAMETHYL 1,3,2 DIOXABOROLAN-2-YL)-1,2,3,4-TETRAHYDROCYCLO-PENT[B]INDOLE
• CAS No.: 919119-69-0
• Molecular Formula: C₁₇H₂₂BNO₂
• Molecular Weight: 283.178
• Mol file: 919119-69-0.mol

Synonyms:Cyclopent[b]indole,1,2,3,4-tetrahydro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl);

Chemical Property of 7-(4,4,5,5 TETRAMETHYL 1,3,2 DIOXABOROLAN-2-YL)-1,2,3,4-TETRAHYDROCYCLO-PENT[B]INDOLE

Chemical Property:

• PSA: 34.25000
• LogP: 2.95580

Purity/Quality:

5-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-1,2,3,4-TETRAHYDROCYCLO-PENT[B]INDOLE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 7-(4,4,5,5 TETRAMETHYL 1,3,2 DIOXABOROLAN-2-YL)-1,2,3,4-TETRAHYDROCYCLO-PENT[B]INDOLE

There total 7 articles about 7-(4,4,5,5 TETRAMETHYL 1,3,2 DIOXABOROLAN-2-YL)-1,2,3,4-TETRAHYDROCYCLO-PENT[B]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: 64.0%

2,3-dihydro-1H-cyclopentindole (2047-91-8) + bis(pinacol)diborane (73183-34-3) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → 7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,4-tetrahydrocyclopenta[b]indole (919119-69-0)

Guidance literature:

With diethylsilane or dimethylchlorosilane/N(CH₂CH₃)3; catalyst: (Ir(C₈H₁₂)Cl)2/(NC₅H₄C(CH₃)3-4)2; [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂; In tetrahydrofuran; react. indole deriv. with silane in toluene at room temp. in the presence of Ru complex, evapn., addn. of boron compds., Ir complex and 4,4'-di-tert-butylbipyridine in THF, react. at 80°C for 8 h; workup with 3 M aq. sodium acetate;

DOI:10.1021/ja1006405

Reference yield: 45.0%

2,3-dihydro-1H-cyclopentindole (2047-91-8) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → 7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,4-tetrahydrocyclopenta[b]indole (919119-69-0)

Guidance literature:

With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; d^tbpy; In hexane; at 60 ℃; for 36h;

DOI:10.1021/ja0631652

Reference yield: 32.0%

2,3-dihydro-1H-cyclopentindole (2047-91-8) + bis(pinacol)diborane (73183-34-3) → 7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,4-tetrahydrocyclopenta[b]indole (919119-69-0) + 7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,4-tetrahydrocyclopenta[b]indole (1180557-84-9)

Guidance literature:

bis(pinacol)diborane; With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 4,4'-di-tert-butyl-2,2'-bipyridine; In tert-butyl methyl ether; Inert atmosphere;

2,3-dihydro-1H-cyclopentindole; In tert-butyl methyl ether; at 80 ℃; for 0.25h; Inert atmosphere; Microwave irradiation;

DOI:10.1021/ol901306m

upstream raw materials:

2,3-dihydro-1H-cyclopentindole

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane

bis(pinacol)diborane

Refernces

• 1、 Robbins, Daniel W.,Boebel, Timothy A.,Hartwig, John F.. "Iridium-catalyzed, silyl-directed borylation of nitrogen-containing heterocycles". . p. 4068 - 4069. Retrieved 2010/05/01.
• 2、 Paul, Sulagna,Chotana, Ghayoor A.,Holmes, Daniel,Reichle, Rebecca C.,Maleczka Jr., Robert E.,Smith III, Milton R.. "Ir-catalyzed functionalization of 2-substituted indoles at the 7-position: Nitrogen-directed aromatic borylation". . p. 15552 - 15553. Retrieved 2007/10/03.