Br[C:2]1[C:3]([CH3:15])=[C:4]2[NH:10][C:9]([CH2:11][CH2:12][CH2:13][CH3:14])=[N:8][C:5]2=[N:6][CH:7]=1.C([Li])(C)(C)C.CO>C1COCC1.CCCCC.[Cl-].[Na+].O>[CH2:11]([C:9]1[NH:10][C:4]2[C:5]([N:8]=1)=[N:6][CH:7]=[CH:2][C:3]=2[CH3:15])[CH2:12][CH2:13][CH3:14]To a cooled (-78° C.) stirred solution of 6-bromo-2-butyl-7-methylimidazo[4,5-b]pyridine (98 mg, 0.366 mmol) in THF (4 mL) was added tert-butyl-lithium (0.86 mL of a 1.7M solution in pentane, 1.46 mmol). After 15 minutes, MeOH (0.5 mL and brine were added the mixture was warmed to room temperature and extracted with EtOAc (4×10 mL). Drying (K2CO3), concentration, and purification (SiO2, 100% EtOAc) gave 60 mg (87%) of the title compound as an oil: 1H NMR (300 MHz, CDCl3) δ8.18 (d, 1H, J=5 Hz), 7.08 (d, 1H, J=5 Hz), 3.05 (t, 2H, J=7.6 Hz), 2.72 (s, 3H), 2.03-1.89 (m, 2H), 1.62-1.43 (m, 2H), 0.96 (t, 3H, J=7.8 Hz).
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