Sodium hydride → HCID 67980735, compound

Participants

Reaction Steps

A solution of 6-(4-(trifluoromethyl)phenyl)pyridazin-3-amine (140 mg, 0.585 mmol) in N,N-dimethylformamide (2 mL) was added to a suspension of 60% sodium hydride (27.2 mg, 0.679 mmol) in N,N-dimethylformamide (2 mL) at 0° C. The mixture was stirred at room temperature for 30 minutes. A mixture of ethyl 4-(1-(methylsulfonyloxy)butyl)benzoate (0.170 g, 0.566 mmol) in N,N-dimethylformamide (3 mL) was then added at room temperature. The reaction was stirred for 2 hours. The reaction was diluted with ethyl acetate and washed with water and brine. The organics were dried over sodium sulfate, filtered and concentrated. Purification by column chromatography (0-15% ethyl acetate in heptanes) gave ethyl 4-(1-(6-(4-(trifluoromethyl)phenyl)pyridazin-3-ylamino)butyl)benzoate (25.0 mg, 10%) as an oil. 1H NMR (400 MHz, CDCl3, δ): 7.98-8.05 (m, 4H), 7.67 (d, J=8.19 Hz, 2H), 7.53 (d, J=9.36 Hz, 1H), 7.44 (d, J=8.19 Hz, 2H), 6.57 (d, J=9.36 Hz, 1H), 5.56-5.67 (m, 1H), 4.82-4.93 (m, 1H), 4.34 (q, J=7.22 Hz, 2H), 1.79-2.01 (m, 2H), 1.36 (t, J=7.22 Hz, 3H), 1.28-1.54 (m, 2H), 0.96 (t, J=7.32 Hz, 3H). MS (M+1): 444.1.

Provenance & Evidence