Reaktion #45439

Reaktionsgleichung

4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

diisopropylethylamine

oxalyl chloride

1-methyl-1H-2-indolecarboxylic acid

→

desired product

Ausbeute 70.2%

1-methyl-N-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-1H-indole-2-carboxamide

Ausbeute 70.2%

Lösungsmittel

dichloromethane

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeAfter one hour the mixture was evaporated
2. 2
   workup.DISSOLUTIONdissolved in dichloromethane (10 mL)
3. 3
   WaschenAfter 16 hours the mixture was washed with water (10 mL)
4. 4
   Trocknendried (MgSO4)
5. 5
   Filtrationfiltered
6. 6
   Einengenconcentrated
7. 7
   Sonstigepurified by flash column chromatography

Vorschrift

A mixture of oxalyl chloride (0.35 mL) and dimethylformamide (1 drop) was added to a solution of 1-methyl-1H-2-indolecarboxylic acid (440 mg, 2.51 mmol) in dichloromethane (10 mL). After one hour the mixture was evaporated, dissolved in dichloromethane (10 mL), and added to a mixture of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (500 mg, 2.28 mmol) and diisopropylethylamine (0.35 mL) in dichloromethane (10 mL). After 16 hours the mixture was washed with water (10 mL), dried (MgSO4), filtered, concentrated, and purified by flash column chromatography to provide the desired product (600 mg, 1.60 mmol) after lyophilization: MS m/e 377.4 (M+H)+.

Quelle