Reacción #88677

Ecuación de reacción

1-bromononane

1,4,6-trimethyl-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine

n-BuLi

THF

→

product

1,4-Dimethyl-6-hexadecyl-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe reaction mixture was quenched by the addition of 10 mL of sat aq NH4Cl at 0° C
2. 2
   ExtracciónThe mixture was extracted with EtOAc
3. 3
   LavadoThe combined organic layer was Washed with brine
4. 4
   Secadodried (MgSO4)
5. 5
   Concentraciónconcentrated under diminished pressure
6. 6
   OtroThe residue was purified by flash chromatography on a silica gel column (25 3.2 cm)
7. 7
   LavadoElution with 10:1 hexanes/ethyl acetate

Procedimiento

To a solution of 277 mg (1.71 mmol) of 1,4,6-trimethyl-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine in 5 mL of THF was added 1.71 mL (2.73 mmol, 1.6 M in hexanes) of n-BuLi followed by 518 μL (1.79 mmol) of 1-bromononane at 78° C. The reaction mixture was slowly warmed to room temperature and stirred for another 16 h. The reaction mixture was quenched by the addition of 10 mL of sat aq NH4Cl at 0° C. The mixture was extracted with EtOAc. The combined organic layer was Washed with brine, dried (MgSO4) and concentrated under diminished pressure. The residue was purified by flash chromatography on a silica gel column (25 3.2 cm). Elution with 10:1 hexanes/ethyl acetate gave the product as a white solid: yield 330 mg (52%); mp 43-45° C.; silica gel TLC Rf 0.25 (8:1:1 hexanes/ethyl acetate/MeOH); 1H NMR (CDCl3) δ 0.88 (t, 3H, J=7.2 Hz), 1.25-1.31 (m, 28H), 1.66 (quint, 2H, J=7.6 Hz), 2.08 (s, 3H), 2.55 (t, 2H, J=8.0 Hz), 2.80 (t, 2H, J=8.4 Hz), 2.90 (s, 3H), 3.38 (t, 2H, J=8.4 Hz) and 6.13 (s, 1H); 13C NMR (CDCl3) δ 14.1, 18.0, 22.7, 24.4, 29.38, 29.38, 29.57, 29.62, 29.65, 29.68, 29.72, 29.72, 29.72, 29.72, 29.72, 29.72, 30.0, 32.0, 33.2, 38.1, 52.4, 112.4, 118.2, 141.0, 159.1 and 163.7; mass spectrum, m/z 372.3 (M+) (theoretical 372.4); mass spectrum (APCI), m/z 373.3574 (M+H)+ (C25H45N2 requires 373.3583).

Fuente