Acetone → 4-(4-((2-Cyanopropan-2-yl)amino)-2-fluorophenyl)butanenitrile

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Reaction Steps

TMSCN (0.37 mL, 2.78 mmol) was added to a mixture of compound 68 (165 mg, 0.93 mmol), acetone (0.41 mL, 5.58 mmol) and ZnCl2 (12 mg, 0.09 mmol) with stirring. The reaction mixture was stirred at room temperature for 1 h, and concentrated in vacuo. The residue was diluted with water and extracted with DCM. The combined organic layers were washed with brine, dried over Na2SO4 and concentrated to dryness to give compound 69 (220 mg, 96%) as a light yellow oil. The crude product was used directly for the next step without purification. 1H NMR (400 MHz, CDCl3) δ7.02-7.10 (m, 1H), 6.58-6.65 (m, 2H), 2.72 (t, 2H, J=7.3 Hz), 2.34 (t, 2H, J=7.1 Hz), 1.90-2.00 (m, 2H), 1.71 (s, 6H).

Provenance & Evidence