Reaktion #2477568

Reaktionsgleichung

product

1-{2-[(6-bromo-2-naphthyl)oxy]ethyl}pyrrolidine

3-cyanophenylboronic acid

sodium carbonate

→

title compound

3-{6-[2-(1-pyrrolidinyl)ethoxy]-2-naphthyl}benzonitrile

Lösungsmittel

isopropanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe mixture was cooled to room temperature
2. 2
   Sonstigepartitioned between 2 M aqueous NaOH and dichloromethane
3. 3
   SonstigeThe aqueous phase was separated
4. 4
   Extraktionextracted with dichloromethane
5. 5
   FiltrationThe combined organic phases were filtered through diatomaceous earth
6. 6
   Einengenconcentrated
7. 7
   Sonstigechromatographed through silica with a gradient of 0%/50%/50% to 10%/40%/50% methanol/ethyl acetate/dichloromethane

Vorschrift

A mixture of the product from Example 37B (35 mg, 0.11 mmol), 3-cyanophenylboronic acid (22 mg, 0.15 mmol), PdCl2(PPh3)2 (4.2 mg, 6 μmol), and isopropanol (0.5 mL) was treated with 2 M aqueous sodium carbonate (80 μL) and heated at 85° C. overnight. The mixture was cooled to room temperature and partitioned between 2 M aqueous NaOH and dichloromethane. The aqueous phase was separated and extracted with dichloromethane. The combined organic phases were filtered through diatomaceous earth, concentrated, and chromatographed through silica with a gradient of 0%/50%/50% to 10%/40%/50% methanol/ethyl acetate/dichloromethane followed by 8% methanol/dichloromethane to provide the title compound. 1HNMR (300 MHz, CD3OD) δ 1.86 (m, 4H), 2.73 (m, 4H), 3.01 (t, 2H), 4.28 (t, 2H), 7.22 (dd, 1H), 7.31 (d, 1H), 7.65 (t, 1H), 7.70 (dt, 1H), 7.75 (dd, 1H), 7.85-7.92 (m, 2H), 8.06 (dt, 1H), 8.07-8.13 (m, 2H); MS (ESI) m/z 343 (M+H)+.

Quelle