反応 #2838

反応方程式

3-ethynyl-3-hydroxyquinuclidine

5-bromo-2-n-butoxypyridine

triethylamine

→

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

収率 25.2%

溶媒

dimethylformamide

反応条件

後処理

1. 1
   温度The reaction mixture was cooled
2. 2
   その他the dimethylformamide and triethylamine were removed by evaporation
3. 3
   workup.ADDITIONThe residue was treated with 2M aqueous sodium hydroxide solution (20 ml)
4. 4
   抽出the resulting mixture extracted with dichloromethane (3×20 ml)
5. 5
   乾燥dried (MgSO4)
6. 6
   その他evaporated
7. 7
   その他to give a brown residue which
8. 8
   その他was crystallised from acetonitrile

実験手順

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).

出典