[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH:8](Br)[CH2:9][F:10])[N:3]=1.[NH:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1.CCN(C(C)C)C(C)C.O>CN(C=O)C>[Br:1][C:2]1[N:3]=[C:4]([CH:8]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[CH2:9][F:10])[CH:5]=[CH:6][CH:7]=1
2-Bromo-6-(1-bromo-2-fluoroethyl)pyridine (70 mg, 0.25 mmol), morpholine (0.022 mL, 0.25 mmol) and DIPEA (0.048 mL, 0.27 mmol) were stirred in DMF (1 mL) at room temperature for 4 hours. Additional morpholine (10.78 μL, 0.12 mmol) and DIPEA (0.024 mL, 0.14 mmol) were added and the resulting solution stirred at room temperature overnight. Water was added and the reaction mixture was extracted with EtOAc (2×). The combined organic extracts were washed with brine, dried over MgSO4, filtered, and concentrated in vacuo. Purification of the residue by silica gel column chromatography (6-50% EtOAc-hexanes) gave the title compound as a pale yellow oil.
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