2-(Tricyclo(3.3.1.1'3,7)dec-1-yl)ethanol → 4-(2-(adamantan-1-yl)ethoxy)-5-chloro-2-fluoro-N-(methylsulfonyl)benzamide

Participants

Reaction Steps

Following the procedure as described in Example 1 and making variations as required to replace 2-cyclopropylethanol with 2-(adamantan-1-yl)ethanol and 2,4,5-trifluoro-N-(methylsulfonyl)benzamide with 5-chloro-2,4-difluoro-N-(methylsulfonyl)-benzamide, the title compound was obtained as a colorless solid (0.04 g, 5%): 1H NMR (300 MHz, DMSO-d6) δ 12.06 (s, 1H), 7.73 (d, J=7.5 Hz, 1H), 7.26 (d, J=12.6 Hz, 1H), 4.15 (t, J=6.9 Hz, 2H), 3.31 (s, 3H), 1.89 (br s, 3H), 1.66-1.51 (m, 14H); 13C NMR (75 MHz, DMSO-d6) δ 162.3 (d, JC-F=2 Hz), 159.9 (d, JC-F=254 Hz), 158.1 (d, JC-F=12 Hz), 130.7 (d, JC-F=4 Hz), 116.5 (d, JC-F=3 Hz), 113.6 (d, JC-F=14 Hz), 102.5 (d, JC-F=28 Hz), 66.1, 42.1, 41.8, 41.2, 36.4, 31.3, 27.9; MS (ES−) m/z 428.1, 430.1 (M−1).

Provenance & Evidence