Reaktion #452988

Reaktionsgleichung

sodium bicarbonate

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

1-hexyne

Water

→

oil

Ausbeute 64.0%

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

Ausbeute 64.0%

Lösungsmittel

NEt3

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe 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), bis(triphenylphosphine)palladium(II) chloride (18 mg, 0.025 mmol) and copper (I) iodide (2 mg, 0.025 mmol) in NEt3 (6.0 mL) was added 1-hexyne (0.237 mL, 2.00 mmol). The mixture was refluxed overnight and 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 an oil (174 mg, 64%). MS (CI/NH3) m/z 273 (M+H(+. 1H NMR (CDCl3, 300 MHz) δ 0.96 (t, J=7.0 Hz, 3H), 1.42-2.10 (m, 8H), 2.26-2.37 (m, 1H), 2.43 (t, J=7.0 Hz, 2H), 2.48 (s, 3H), 2.63-2.71 (m, 1H), 3.08-3.16 (m, 1H), 3.88-4.03 (m, 2H), 4.47-4.55 (m, 1H), 7.17-7.21 (m, 1H), 8.19-8.23 (m, 2H).

Quelle