4'-(Trifluoromethyl)[1,1'-biphenyl]-3-methanol → [7-(4'-Trifluoromethyl-biphenyl-3-ylmethylsulfanyl)-indan-4-yloxy]-acetic Acid

Participants

Reaction Steps

Preparation of (4′-Trifluoromethyl-biphenyl-3-yl)-methanol (compound 48A) The title compound was prepared in the manner analogous to Example 3A with 1-bromo-4-trifluoromethyl-benzene and 3-(hydroxymethyl)phenyl boronic acid. MS m/z 251 (M−1). Step 2. Preparation of 3-Chloromethyl-4′-trifluoromethyl-biphenyl (compound 48B) The title compound was prepared in the manner analogous to Example 3B using 48A. MS m/z 236 (M+1-Cl). Step 3. Preparation of [7-(4′-Trifluoromethyl-biphenyl-3-ylmethylsulfanyl)-indan-4-yloxy]-acetic acid methyl ester (compound 48C) The title compound was prepared in the manner analogous to Example 1F using 12C and 48B. MS m/z 473 (M+1). Step 4. Preparation of [7-(4′-Trifluoromethyl-biphenyl-3-ylmethylsulfanyl)-indan-4-yloxy]-acetic acid (compound 48) The title compound was prepared in the manner analogous to Example 1 using 48C. 400 MHz 1H NMR (DMSO-d6) δ 12.96 (br(s), 1H), 7.75 (d, 2H, J=8.3 Hz), 7.67 (d, 2H, J=8.1 Hz), 7.52 (m, 1H), 7.37 (t, 1H, J=7.6 Hz), 7.29 (m, 2H), 7.13 (d, 1H, J=8.5 Hz), 6.61 (d, 1H, J=8.5 Hz), 4.63 (s, 2H), 4.05 (s, 2H), 2.71 (t, 2H), 2.58 (t, 2H), 1.81 (m, 2H). MS m/z 459 (M+1).

Provenance & Evidence