{7-[3-(5-Trifluoromethyl-pyridin-2-yl)-benzylsulfanyl]-indan-4-yloxy}-acetic acid methyl ester → {7-[3-(5-Trifluoromethyl-pyridin-2-yl)-benzylsulfanyl]-indan-4-yloxy}-acetic acid

Participants

Reaction Steps

Preparation of [3-(5-Trifluoromethyl-pyridin-2-yl)-phenyl]-methanol (compound 53A) The title compound was prepared in the manner analogous to Example 3A using 3-(hydroxymethyl)phenyl boronic acid and 2-chloro-5-trifluoromethyl-pyridine. MS m/z 253 (M+1). Step 2. Preparation of 2-(3-Chloromethyl-phenyl)-5-trifluoromethyl-pyridine (compound 53B) The title compound was prepared in the manner analogous to Example 3B using 53A. MS m/z 237 (M+1-Cl). Step 3. Preparation of {7-[3-(5-Trifluoromethyl-pyridin-2-yl)-benzylsulfanyl]-indan-4-yloxy}-acetic acid methyl ester (compound 53C) The title compound was prepared in the manner analogous to Example 1F using 12C and 53B. MS m/z 474 (M+1). Step 4. Preparation of {7 -[3-(5-Trifluoromethyl-pyridin-2-yl)-benzylsulfanyl]-indan-4-yloxy}-acetic acid (compound 53) The title compound was prepared in the manner analogous to Example 1 using 53C. 400 MHz 1H NMR (DMSO-d6) δ 8.98 (m, 1H), 8.23 (dd, 1H, J=1.7 Hz, J′=8.5 Hz), 7.99 (m, 2H), 7.87 (s, 1H), 7.39 (t, 1H, J=7.6 Hz), 7.33 (m, 1H), 7.11 (d, 1H, J=8.5 Hz), 6.58 (d, 1H, J=8.5 Hz), 4.61 (s, 2H), 4.08 (s, 2H), 2.70 (t, 2H, J=7.3 Hz), 2.63 (t, 2H, J=7.6 Hz), 1.84 (m, 2H). MS m/z 460 (M+1).

Provenance & Evidence