1-Bromononane → 1,4-Dimethyl-6-decyl-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine

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To a solution of 181 mg (1.12 mmol) of 1,4,6-trimethyl-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine in 3 mL of THF was added 1.19 mL (1.90 mmol, 1.6 M in hexanes) of n-BuLi followed by 255 μL (1.34 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 yellow oil: yield 210 mg (66%); silica gel TLC Rf 0.18 (8:1:1 hexanes/ethyl acetate/MeOH); 1H NMR (CDCl3) δ 0.86 (t, 3H, J=6.8 Hz), 1.24-1.30 (m, 16H), 1.65 (quint, 2H, J=7.6 Hz), 2.08 (s, 3H), 2.54 (t, 2H, J=8.0 Hz), 2.81 (t, 2H, J=8.0 Hz), 2.90 (s, 3H), 3.38 (t, 2H, J=8.0 Hz) and 6.13 (s, 1H); 13C NMR (CDCl3) δ 14.2, 18.1, 22.8, 24.5, 29.5, 29.68, 29.73, 29.75, 29.77, 30.1, 32.1, 33.4, 38.2, 52.6, 112.6, 118.4, 141.3, 159.3 and 163.9; mass spectrum, m/z 288.3 (M+) (theoretical 288.3); mass spectrum (APCI), m/z 289.2653 (M+H)+ (C19H33N2 requires 289.2644).

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