반응 #88683

반응 방정식

n-BuLi

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

1-bromoheptane

→

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

용매

THF

반응 조건

후처리

1. 1
   기타The reaction mixture was quenched by the addition of 25 mL of sat aq. NH4Cl at 0° C
2. 2
   추출The mixture was extracted with three 40-mL portions, of EtOAc
3. 3
   세척The combined organic layer was washed with brine
4. 4
   건조dried over anhydrous MgSO4
5. 5
   여과filtered
6. 6
   농축concentrated under diminished pressure
7. 7
   기타The residue was purified via flash chromatography on a silica gel column (42×2.5 cm)
8. 8
   세척Step gradient elution with 1:10→1:4 ethyl acetate-hexanes as eluent

실험 절차

To a solution containing −490 mg (2.71 mmol) of 1,4,6-Trimethyl-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine in 7.2 mL of THF was added 2.70 mL (4.34 mmol) of n-BuLi (1.6 M in hexanes) followed by 4504 (509 mg, 2.85 mmol) of 1-bromoheptane at −78° C. The reaction mixture was slowly warmed to room temperature and stirred for 16 h. The reaction mixture was quenched by the addition of 25 mL of sat aq. NH4Cl at 0° C. The mixture was extracted with three 40-mL portions, of EtOAc. The combined organic layer was washed with brine, dried over anhydrous MgSO4, filtered, and concentrated under diminished pressure. The residue was purified via flash chromatography on a silica gel column (42×2.5 cm). Step gradient elution with 1:10→1:4 ethyl acetate-hexanes as eluent gave 1,4-dimethyl-6-octyl-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine as a yellow oil: yield 402 mg (57%); silica gel TLC Rf 0.36 (8:1:1 hexanes-ethyl acetate-methanol); 1H NMR (CDCl3) δ 0.79 (t, 2H, J=7.2 Hz), 1.16-1.30 (m, 10H), 1.58 (quint, 2H, J=8.0 Hz), 2.00 (s, 3H), 2.48 (t, 2H, J=8.0 Hz), 2.72 (t, 2H, J=8.4 Hz), 2.82 (s, 3H), 3.38 (t, 2H, J=8.4 Hz), 6.14 (s, 1H).

출처