Reaktion #452986

Reaktionsgleichung

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

sodium carbonate

1-naphthaleneboronic acid

sodium bicarbonate

→

oil

Ausbeute 62.0%

5-(1-Naphthalenyl)-3-(1-methyl-2-(S)-pyrrolidinylmethoxy)pyridine

Ausbeute 62.0%

Lösungsmittel

benzene

Water

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction mixture was refluxed overnight
2. 2
   ExtraktionThe mixture was extracted with EtOAc, which
3. 3
   Trocknenwas dried over MgSO4
4. 4
   Filtrationfiltered
5. 5
   Einengenconcentrated
6. 6
   SonstigeThe residue was chromatographed on a silica gel column
7. 7
   Wascheneluting with NH4OH/MeOH/EtOAc 0:1:9 and 1:10:90

Vorschrift

To a solution of 5-bromo-3-(1-methyl-2-(S)-pyrrolidinylmethoxy)-pyridine (272 mg, 1.00 mmol) in benzene (2.0 mL) were added aqueous sodium carbonate (2.0M, 1.0 mL), tetrakis(triphenylphosphine)palladium(0) (35 mg, 0.03 mmol) and 1-naphthaleneboronic acid (189 mg, 1.10 mmol). The reaction mixture was refluxed overnight, then cooled to room temperature. Water (2 mL) was added, and solid sodium bicarbonate was added until the aqueous layer was saturated. The mixture was extracted with EtOAc, which was dried over MgSO4, filtered and concentrated. The residue was chromatographed on a silica gel column, eluting with NH4OH/MeOH/EtOAc 0:1:9 and 1:10:90 to afford a light yellowish oil (196 mg, 62%). MS (CI/NH3) m/z 319 (M+H)+. 1H NMR (CDCl3, 300 MHz) δ 1.71-1.92 (m, 3H), 2.00-2.10 (m, 1H), 2.27-2.38 (m, 1H), 2.51 (s, 3H), 2.66-2.75 (m, 1H), 3.09-3.17 (m, 1H), 3.98-4.14 (m, 2H), 7.34-7.57 (m, 5H), 7.72-7.96 (m, 3H),8.36-8.43 (m, 1H).

Quelle