{7-[3-(4-Trifluoromethyl-benzyloxy)-benzylsulfanyl]-indan-4-yloxy}-acetic acid methyl ester → HCID 22280149, compound

Participants

Reaction Steps

Preparation of [3-(4-trifluoromethyl-benzyloxy)-phenyl]-methanol (compound 79A) The title compound was prepared in the manner analogous to Example 14A using 1-bromomethyl-4-trifluoromethyl-benzene and 3-hydroxymethyl-phenol. MS m/z 265(M-OH). Step 2. Preparation of 1-(4-trifluoromethyl-benzyloxy)-3-chloromethyl-benzene (compound 79B) The title compound was prepared in the manner analogous to Example 3B using 79A. MS m/z 265 (M-Cl). Step 3. Preparation of {7-[3-(4-Trifluoromethyl-benzyloxy)-benzylsulfanyl]-indan-4-yloxy}-acetic acid methyl ester (compound 79C) The title compound was prepared in the manner analogous to Example 1F using 79B and 12C. MS m/z 503 (M+1). Step 4. Preparation of {7-[3-(4-Trifluoromethyl-benzyloxy)-benzylsulfanyl]-indan-4-yloxy}-acetic acid (compound 79) The title compound was prepared in the manner analogous to Example 1 using 79C. mp 145-146° C.; IR (KBr) cm−1: 3076, 3028, 1705, 1318, 1232, 1109; 400 MHz 1H NMR (DMSO-d6): δ 12.94 (br(s), 1H), 7.71 (d, 2H, J=8.2 Hz), 7.59 (d, 2H, J=8.0 Hz), 7.10-7.19 (m, 1H), 7.05 (d, 1H, J=8.5 Hz), 6.75-6.86 (m, 4H), 6.58 (d, 1H, J=8.5 Hz), 5.08 (s, 2H), 4.61 (s, 2H), 3.95 (s, 2H), 2.75 (t, 2H, J=7.5 Hz), 2.64 (t, 2H, J=7.5 Hz), 1.88 (pentet, 2H); MS m/z 487 (M−1). Anal. Calc'd for C26H23F3O4S: C, 63.92; H, 4.75; found: C, 63.78; H, 4.53.

Provenance & Evidence