ChemicalBook CAS DataBase List 1-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole

1-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole synthesis

10synthesis methods

Product Name:1-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole
CAS Number:837392-62-8
Molecular formula:C15H20BNO2
Molecular Weight:257.14

603-76-9
433 suppliers
$18.00/5g

76-09-5 Synthesis

76-09-5
391 suppliers
$8.19/250mg

274-07-7
169 suppliers
$78.09/5g

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

837392-62-8
122 suppliers
$19.00/250mg

1-METHYL-3-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-1H-INDOLE

683229-61-0
56 suppliers
$37.00/250mg

Yield: 67 %Spectr. ， 13 %Spectr.

Reaction Conditions:

Stage #1:1-methylindole;benzo[1,3,2]dioxaborole with thiophene;tris(pentafluorophenyl)borate in 1,2-dichloro-ethane at 80; for 40 h;Schlenk technique;Inert atmosphere;
Stage #2:2,3-dimethyl-2,3-butane diol with triethylamine in 1,2-dichloro-ethane at 20;Schlenk technique;Inert atmosphere;

Steps:

General Procedure for Catalytic Arene Borylation:
General procedure: In a 20 mL Schlenk tube under Ar, B(C6F5)3 (51.2 mg, 0.10 mmol) was dissolved in distilled1,2-dichloroethane (2 mL), followed by the addition of catecholborane (2, 117 μL, 1.1 mmol) andtetrahydrothiophene (9 μL, 0.10 mmol). Then, to the mixture was added the arene substrate (1.0mmol), and the resulting mixture was heated to 80 °C (oil bath temp.) and stirred for the appropriatereaction time. After cooling to room temperature, excess Et3N (2 mL, ca. 15 mmol) and then, pinacol(355 mg, 3 mmol) were added to the reaction mixture and stirred. The reaction mixture wasquenched by aqueous NH4Cl, extracted with EtOAc, washed with brine, and dried over Na2SO4.Purification by silica gel column chromatography (eluent: CH2Cl2/hexane) was performed to affordthe borylated products.

References:

Kitani, Fumiya;Takita, Ryo;Imahori, Tatsushi;Uchiyama, Masanobu [Heterocycles,2017,vol. 95,# 1,p. 158 - 166]