C(=O)([O-])[O-].[K+].[K+].[CH2:7]([O:11][C:12]1[N:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=1)[CH:8]([CH3:10])[CH3:9].[Br:19][C:20]1[CH:21]=[C:22]([CH:25]=[CH:26][C:27]=1F)[C:23]#[N:24]>CS(C)=O.O>[Br:19][C:20]1[CH:21]=[C:22]([CH:25]=[CH:26][C:27]=1[O:18][C:15]1[CH:16]=[N:17][C:12]([O:11][CH2:7][CH:8]([CH3:10])[CH3:9])=[CH:13][CH:14]=1)[C:23]#[N:24]Potassium carbonate (0.622, 4.50 mmol) and 6-isobutoxypyridin-3-ol (Preparation 7, 0.251 g, 1.50 mmol) were added to a solution of 3-bromo-4-fluorobenzonitrile (0.300 g, 1.50 mmol) in DMSO (7 mL). The reaction was heated at 80° C. for a total of 4 hours and then allowed to cool to room temperature. The mixture was diluted with water (50 mL) and extracted with DCM (3×30 mL). The combined organics were washed with brine (2×50 mL), filtered and concentrated in vacuo to yield the title compound as a solid (0.508 g).
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