(Diethylamino)sulfur trifluoride → HCID 67422345, compound

Participants

Reaction Steps

To a cold (0° C.) solution of [2-(3,3″-dimethyl-3′,4′,5′,6′-tetrahydro-2′H-[2,2′;6′,2″]terpyridin-1′-ylmethyl)-phenyl]-methanol (0.107 g,0.28 mmol) in CH2Cl2 (3 mL) was added (diethylamino)sulfur trifluoride (80 μL, 0.61 mmol). After 15 minutes, the cooling bath was removed and the reaction mixture was warmed to room temperature. After an additional 3 hours, the reaction mixture was treated with saturated aqueous NaHCO3 (5 mL) and extracted with CH2Cl2 (4×10 mL). The combined organic extracts were dried (Na2SO4) and concentrated. Purification of the crude material by radial chromatography on silica gel (1 mm plate, 100:1:1 CH2Cl2—CH3OH—NH4OH) provided 0.032 g (29%) of COMPOUND 62 as a white solid. 1H NMR (CDCl3) δ 1.60-1.74 (m, 3H), 2.02-2.10 (m, 1H), 2.26-2.41 (m, 8H), 3.56 (s, 2H), 4.13 (d, 2H, J=11.1 Hz), 5.06 (d, 2H, JC-F=48 Hz), 6.81-6.88 (m, 5H), 7.14-7.16 (m, 3H), 8.31 (d, 2H, J=3.6 Hz). 13C NMR (CDCl3) δ 19.24, 25.64, 28.65, 50.09, 67.20, 82.93 (d, JC-F=648 Hz), 122.29, 125.94, 127.47, 127.62, 129.79, 132.36, 133.66 (d, JC-F=62 Hz), 138.14, 139.34, 146.63, 159.99; ES-MS m/z 390 (M+H). Anal. Calcd. For C25H28N3F.0.1H2O: C, 76.73; H, 7.26; N, 10.74. Found: C, 76.66; H, 7.23; N, 10.70.

Provenance & Evidence