Reaktion #357177

Reaktionsgleichung

7-bromo-isoquinoline-5-sulfonic acid (2-amino-ethyl)-amide carbamic acid t-butyl ester

2-phenyl-1,3,2-dioxaborinane

Na2CO3

→

7-phenyl-isoquinoline-5-sulfonic acid (2-amino-ethyl)-amide carbamic acid t-butyl ester

Ausbeute 97.0%

Lösungsmittel

EtOAc

ethylene glycol dimethyl ether

CH3OH

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturAfter cooling to room temperature
2. 2
   Filtrationfiltered
3. 3
   Einengenconcentrated
4. 4
   workup.DISSOLUTIONThe residue is dissolved in EtOAc
5. 5
   Waschenwashed with brine
6. 6
   Trocknendried over Na2SO4
7. 7
   SonstigeThe crude material is chromatographed on silica gel (gradient 50% EtOAc in hexane)

Vorschrift

A mixture of 7-bromo-isoquinoline-5-sulfonic acid (2-amino-ethyl)-amide carbamic acid t-butyl ester (1.50 g, 3.49 mmol), 2-phenyl-1,3,2-dioxaborinane (1.129 g, 6.98 mmol), Pd(dppb)Cl2 (211 mg, 0.0349 mmol) and Na2CO3 (2.0M, 12 mL) in ethylene glycol dimethyl ether (60 mL) and CH3OH (15 mL) is heated to 80° C. (oil bath) with stirring overnight. After cooling to room temperature, the mixture is diluted with EtOAc, filtered and concentrated. The residue is dissolved in EtOAc, washed with brine and dried over Na2SO4. The crude material is chromatographed on silica gel (gradient 50% EtOAc in hexane) to give 1.45 g (97% yield) 7-phenyl-isoquinoline-5-sulfonic acid (2-amino-ethyl)-amide carbamic acid t-butyl ester.

Quelle