Triethylamine → 2-(1-Adamantyloxycarbonyl)-4-(4-fluorophenyl)-5-[4-(Methylsulfonyl)phenyl]-3(2H)-pyridazinone

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Reaction Steps

A solution of 4-(4-fluorophenyl)-5-[4-(methylsulfonyl)phenyl]-3(2H)-pyridazinone, prepared according to the procedure of Example 11 (200 mg, 0.58 mmol) in CH2Cl2 (8 ml) was prepared and stirred. 1-Adamantylfluoroformate (172 mg, 0.87 mmol), dimethylaminopyridine (14 mg, 0.011 mmol) and triethylamine (0.12 ml, 0.87 mmol) were added. The reaction mixture was stirred at room temperature overnight. The reaction mixture was diluted with CH2Cl2 (50 ml) and washed with 10% citric acid (50 ml), brine (50 ml) and dried over MgSO4, and concentrated in vacuo. The resulting crude residue was purified using flash chromatography (SiO2, eluting with 15:1 CH2Cl2:diethyl ether) to provide the desired product (yield: 55 mg, 18%). 1H NMR (300 MHz, DMSO-d4) δ 1.66 (bs, 6H), 2.25 (bd, 10H), 3.21 (s, 3H), 7.15 (t, 2H), 7.24 (m, 2H), 7.6 (dd, 2H), 7.88 (d, J=9 Hz, 2H), 8.15 (s, 1H). MS (ESI) m/z 521 (M−H)+. Anal. calc. for C21H15F N2O3S2: C 64.35; H, 5.20; N, 5.36.

Provenance & Evidence