HCID 20827072, compound → HCID 22280130, compound

Participants

Reaction Steps

Preparation of [3-(4Chloro-3-trifluoromethyl-benzyloxy)-phenyl]-methanol (compound 80A) The title compound was prepared in the manner analogous to Example 14A using 4-bromomethyl-1chloro-2-trifluoromethyl-benzene and 3-hydroxymethyl-phenol. MS m/z 299 (M-OH). Step 2. Preparation of 1-Chloro-4-(3-chloromethyl-phenoxymethyl)-2-trifluoromethyl-benzene (compound 80B) The title compound was prepared in the manner analogous to Example 3B using 80A. MS m/z 299 (M-Cl). Step 3. Preparation of {7-[3-(4-Chloro-3-trifluoromethyl-benzyloxy)-benzylsulfanyl]-indan-4-yloxy}-acetic acid methyl ester (compound 80C) The title compound was prepared in the manner analogous to Example 1F using 80B and 12C. MS m/z 537 (M+1). Step 4. Preparation of {7-[3-(4-Chloro-3-trifluoromethyl-benzyloxy)-benzylsulfanyl]-indan-4-yloxy}-acetic acid (compound 80) The title compound was prepared in the manner analogous to Example 1 using 80C. mp 121-122° C.; IR (KBr) cm−1: 3027, 2584, 1742, 1255, 1129, 1109; 400 MHz 1H NMR (DMSO-d6): δ 12.95 (br(s), 1H), 7.87 (s, 1H), 7.64-7.75 (m, 2H), 7.09-7.19 (m, 1H), 7.01-7.09 (m, 1H), 6.73-6.88 (m, 3H), 6.56 (d, 1H, J=8.5 Hz), 5.06 (s, 2H), 4.60 (s, 2H), 3.95 (s, 2H), 2.74 (t, 2H, J=7.4 Hz), 2.63 (t, 2H, J=7.4 Hz), 1.87 (pentet, 2H); MS m/z 523 (M+1). Anal. Calc'd for C26H22ClF3O4S: C, 59.71; H, 4.24; found: C, 59.45; H, 4.08.

Provenance & Evidence