Reaktion #1867488

Reaktionsgleichung

5-bromo-3-(1-BOC-2-(S)-pyrrolidinylmethoxy)pyridine

4-chlorophenylboronic acid

Na2CO3

→

title compound

Ausbeute 134.0%

5-(4-chlorophenyl)-3-(2-(R)-pyrrolidinylmethoxy)pyridine

Ausbeute 134.0%

Lösungsmittel

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwas heated
2. 2
   Temperaturat reflux for 6 hours
3. 3
   SonstigeThe solvent was removed under vacuum
4. 4
   Sonstigethe residue was chromatographed on a silica gel column
5. 5
   Wascheneluting with 1:5 to 1:2 ethyl acetate/hexane

Vorschrift

To a solution of 5-bromo-3-(1-BOC-2-(S)-pyrrolidinylmethoxy)pyridine (300 mg, 0.84 mmol) and 4-chlorophenylboronic acid (263 mg, 1.68 mmol, Lancaster Chemical Co.) in toluene (10 mL) was added Pd(0) (25 mg) and Na2CO3 (1 mL of a 2M solution), and the mixture was heated at reflux for 6 hours. The solvent was removed under vacuum, and the residue was chromatographed on a silica gel column, eluting with 1:5 to 1:2 ethyl acetate/hexane to afford the title compound (325 mg, 100% yield). MS (DCI/NH3) m/z 389 (M+H)+. 1H NMR (CDCl3, 300 MHz) δ: 1.47 (s, 9h), 1.90 (m, 2H), 2.05 (br, 1H), 3.40 (br, 2H), 3.92 (br, 1H), 4.19 (br, 2H), 4.25 (br, 1H), 7.44 (m, 2H), 7.52 (m, 3H), 8.31 (m, 1H), 8.42 (s, 1H).

Quelle