Reaktion #68417

Reaktionsgleichung

1-benzyl-3-(3,4-difluorobenzylcarbamoyl)-2-isopropyl-1H-indol-6-yl trifluoromethanesulfonate

Compound 160

1-benzyl-3-(3,4-difluorobenzylcarbamoyl)-2-isopropyl-1H-indol-6-yl trifluoromethanesulfonate

pyridin-4-ylboronic acid

K2CO3

LiCl

→

title compound

1-Benzyl-N-(3,4-difluorobenzyl)-2-isopropyl-6-(pyridin-4-yl)-1H-indole-3-carboxamide

Lösungsmittel

toluene

MeOH

H2O

EtOAc

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction was then cooled to room temperature
2. 2
   Waschenwashed with brine
3. 3
   Trocknendried over Na2SO4
4. 4
   Einengenconcentrated in vacuo
5. 5
   SonstigeThe residue was purified by chromatography on silica gel (0→100% EtOAc-hexanes)

Vorschrift

General Procedure W. A mixture of 1-benzyl-3-(3,4-difluorobenzylcarbamoyl)-2-isopropyl-1H-indol-6-yl trifluoromethanesulfonate (Compound 160, 50 mg, 0.088 mmol), pyridin-4-ylboronic acid (22 mg, 0.18 mmol), Pd(PPh3)4 (5.0 mg, 0.0043 mmol), K2CO3 (61 mg, 0.44 mmol), and LiCl (19 mg, 0.44 mmol) in toluene (3 ml), MeOH (1 ml), and H2O (0.5 ml) was heated at 90° C. for 16 h. The reaction was then cooled to room temperature, diluted with EtOAc, washed with brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by chromatography on silica gel (0→100% EtOAc-hexanes) to yield the title compound.

Quelle