반응 #2838

반응 방정식

3-ethynyl-3-hydroxyquinuclidine

5-bromo-2-n-butoxypyridine

triethylamine

→

3-[2-(6-butoxy-3-pyridyl)ethynyl]quinuclidin-3-ol

수율 25.2%

용매

dimethylformamide

반응 조건

후처리

1. 1
   온도The reaction mixture was cooled
2. 2
   기타the dimethylformamide and triethylamine were removed by evaporation
3. 3
   workup.ADDITIONThe residue was treated with 2M aqueous sodium hydroxide solution (20 ml)
4. 4
   추출the resulting mixture extracted with dichloromethane (3×20 ml)
5. 5
   건조dried (MgSO4)
6. 6
   기타evaporated
7. 7
   기타to give a brown residue which
8. 8
   기타was crystallised from acetonitrile

실험 절차

A stirred mixture of 3-ethynyl-3-hydroxyquinuclidine (600 mg), 5-bromo-2-n-butoxypyridine (920 mg), bis-(triphenylphosphine)-palladium (II) chloride (140 mg), copper (I) iodide (70 mg) and dry triethylamine (10 ml) in dry dimethylformamide (20 ml) was heated at 90° C. under an atmosphere of argon for 6 hours. The reaction mixture was cooled and the dimethylformamide and triethylamine were removed by evaporation. The residue was treated with 2M aqueous sodium hydroxide solution (20 ml) and the resulting mixture extracted with dichloromethane (3×20 ml). The organic extracts were combined, dried (MgSO4) and evaporated to give a brown residue which was crystallised from acetonitrile to yield 3-[2-(6-butoxy-3-pyridyl)ethynyl]quinuclidin-3-ol (300 mg) as a solid, m.p. 149°-151° C.; microanalysis, found: C, 71.3; H, 7.9; N, 8.9%; C18H24N2O2 0.1H 2O requires: C, 71.47; H, 8.08; N, 9.26%; NMR (DHSOd6): 0.9-1.0(3H, t), 1.2-1.35(1H, m), 1.35-1.5(2H, m), 1.5-1.65(1H, m), 1.65-1.75(2H, m), 1.75-2.0(3H, m), 2.6-2.75(4H, t), 2.8-2.85(1H, d), 3.02-3.17(1H, d), 4.2-4.3(2H, t), 5.55(1H, s), 6.75-6.83(1H, d), 7.65-7.72(1H, d) and 8.2(1H, s); m/Z 301 (M+H).

출처