Water → HCID 86618700, compound

Participants

Reaction Steps

2-(4-Chlorophenyl)thieno[2,3-d]pyridazin-7(6H)-one (285 mg, 1.1 mmol) was added to dry DMF (5 mL) and NaH (71 mg, 55% in mineral oil, 1.6 mmol) was added in small potions and stirred 10 min. tert-butyl (2R)-2-{[(6-{[(methylsulfonyl)oxy]methyl}pyridin-2-yl)oxy]methyl}pyrrolidine-1-carboxylate (420 mg, 1.1 mmol) dissolved in dry DMF (3 mL) was added drop wise and the reaction mixture was stirred at ambient temperature for 3 h. Water was added and the aqueous phase was extracted three times with DCM. The organic phase was evaporated and purified by flash chromatography using a gradient of EtOAc/heptane to give the title compound as a yellow solid. Yield: 380 mg (63%). 1H NMR (399.961 MHz, CDCl3) δ 8.22 (s, 1H), 7.64 (d, J=8.7 Hz, 2H), 7.53-7.42 (m, 4H), 6.72 (d, J=7.3 Hz, 1H), 6.61 (d, J=8.1 Hz, 1H), 5.48 (s, 2H), 4.41-4.01 (m, 3H), 3.43-3.25 (m, 2H), 1.97-1.74 (m, 4H), 1.42 (s, 9H). MS (ESI+) 553.3 (M+1H+)

Provenance & Evidence