[CH3:1][O:2][CH2:3][CH2:4][OH:5].CC(C)([O-])C.[K+].[Br:12][C:13]1[CH:14]=[CH:15][C:16](Cl)=[N:17][CH:18]=1>O1CCOCC1.[Cl-].[Na+].O>[Br:12][C:13]1[CH:14]=[CH:15][C:16]([O:5][CH2:4][CH2:3][O:2][CH3:1])=[N:17][CH:18]=12-Methoxyethanol (5.12 mL, 85.0 mmol) was dissolved in 1,4-dioxane (125 ml). Potassium tert-butoxide (7.00 g, 62.4 mmol) was added under N2. The mixture was stirred for 10 minutes. 5-Bromo-2-chloropyridine (10.0 g, 52.0 mmol) was added and the resulting mixture was refluxed for 2 hours. The mixture was poured into brine and extracted with EtOAc. The organic layer was washed with brine, dried over MgSO4 and evaporated to dryness. Purification by flash chromatography (silica, heptanes/EtOAc 4:1) gave the title compound as a colorless oil (8.74 g, 73%) sufficiently pure for the next step.
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