Cl[C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][N:3]=1.[F:9][C:10]1([F:16])[CH2:13][CH:12]([C:14]#[N:15])[CH2:11]1.C1(C)C=CC=CC=1.C[Si](C)(C)[N-][Si](C)(C)C.[Na+]>CCOC(C)=O.O>[Cl:8][C:7]1[C:2]([C:12]2([C:14]#[N:15])[CH2:13][C:10]([F:16])([F:9])[CH2:11]2)=[N:3][CH:4]=[CH:5][CH:6]=1
To a 100 mL round bottom flask was added 2,3-dichloropyridine (2.9 g, 20 mmol), 3,3-difluorocyclobutanecarbonitrile (2.1 g, 18 mmol), and toluene (50 mL). The mixture was cooled to ° C. and sodium hexamethyldisilazide (NaHMDS, 2.0 M in THF, 11 mL, 22 mmol) was added. The reaction mixture was warmed to rt and stirred for 2 h. The mixture was then diluted with EtOAc (20 mL) and water (20 mL). The aqueous layer was extracted with EtOAc and the combined organic phases were washed with brine, dried over Na2SO4, and concentrated to provide the desired product (3.4 g) as a colorless oil.
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