Reaktion #91523

Reaktionsgleichung

7-bromo-1-chloroisoquinoline

5-indoleboronic acid

potassium carbonate

→

yellow solid

Ausbeute 25.0%

1-Chloro-7-(1H-indol-5-yl)-isoquinoline

Ausbeute 25.0%

Lösungsmittel

N,N-dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigewhile purging the headspace with argon for 30 min
2. 2
   Temperaturto reflux for 16 h
3. 3
   FiltrationThe mixture was filtered through a bed of silica gel
4. 4
   workup.ADDITIONdiluted with water (50 mL)
5. 5
   Extraktionextracted with ethyl acetate (50 mL)
6. 6
   SonstigeThe organic layer was separated
7. 7
   Waschenwashed with NaOH (2×20 mL, 10% aq.), water (5×30 mL
8. 8
   Sonstigeflash-chromatographed (ethyl acetate/hexanes)

Vorschrift

A mixture of 7-bromo-1-chloroisoquinoline (0.50 g, 2.1 mmol), 5-indoleboronic acid (0.40 g, 2.5 mmol), tetrakis(triphenylphosphene)palladium (0.035 g, 0.08 mmol), potassium carbonate (2.1 mL, 2 M, 4.1 mmol), N,N-dimethylformamide (11 mL) was stirred while purging the headspace with argon for 30 min. The mixture was then brought to reflux for 16 h before being allowed to cool to RT. The mixture was filtered through a bed of silica gel, diluted with water (50 mL), and extracted with ethyl acetate (50 mL). The organic layer was separated and washed with NaOH (2×20 mL, 10% aq.), water (5×30 mL, until refractive changes were no longer seen at the organic-aqueous interface), and ammonium chloride (20 mL, sat.). The organic layer was then adsorbed onto silica gel and flash-chromatographed (ethyl acetate/hexanes) to afford 0.14 g (25%) of a yellow solid. MS (ESI): calculated for C17H11ClN2, 278.1. found 301.0 [M+Na]+. 1H NMR (300 MHz, DMSO-d6) δ 6.56-6.58 (m, 1H), 7.44 (t, J=2.77 Hz, 1H), 7.57-7.59 (m, 2H), 7.93 (m, 1H), 8.04 (s, 1H), 8.13-8.20 (m, 1H), 8.27-8.31 (m, 2H), 8.43 (m, 1H), 11.25 (brs, 1H).

Quelle