Reacción #452990

Ecuación de reacción

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

1-decyne

sodium bicarbonate

Water

→

oil

Rendimiento 85.0%

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

Rendimiento 85.0%

Disolventes

CH2Cl2

NEt3

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe mixture was refluxed overnight
2. 2
   ExtracciónThe mixture was extracted with EtOAc, which
3. 3
   Secadowas dried over MgSO4
4. 4
   Filtraciónfiltered
5. 5
   Concentraciónconcentrated
6. 6
   OtroThe residue was chromatographed on a silica gel column
7. 7
   Lavadoeluting with NH4OH/MeOH/EtOAc 0:1:9 and 1:10:90

Procedimiento

To a solution of 5-bromo-3-(1-methyl-2-(S)-pyrrolidinylmethoxy)-pyridine (544 mg, 2.00 mmol), bis(triphenylphosphine)palladium(II) chloride (28 mg, 0.038 mmol) and copper (I) iodide (5 mg, 0.038 mmol) in CH2Cl2 (3.0 mL) and NEt3 (1.0 mL) was added 1-decyne (0.553 mL, 3.00 mmol). The 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 an oil (543 mg, 85%). MS (CI/NH3) m/z 329 (M+H)+. 1H NMR (CDCl3, 300 MHz) δ 0.90 (t, J=6.9 Hz, 3H), 1.23-2.10 (m, 14H), 2.25-2.41 (m, 1H), 2.41 (t, J=7.3 Hz, 2H), 2.50 (s, 3H), 2.60-2.75 (m, 1H), 3.08-3.21 (m, 1H),, 3.89-4.06 (m, 2H), 7.19 (s, 1H), 8.15-8.28 (m, 2H).

Fuente