HCID 20827096, compound → HCID 22280077, compound

Participants

Reaction Steps

Preparation of [4-Methoxy-3-(4-trifluoromethyl-benzyloxy)-phenyl]-methanol (compound 78A) The title compound was prepared in the manner analogous to Example 14A using 1-bromomethyl-4-trifluoromethyl-benzene and 5-hydroxymethyl-2-methoxy-phenol. MS m/z 295 (M-OH). Step 2. Preparation of 4-Chloromethyl-1-methoxy-2-(4-trifluoromethyl-benzyloxy)-benzene (compound 78B) The title compound was prepared in the manner analogous to Example 3B using 78A. MS m/z 295 (M-Cl). Step 3. Preparation of {7-[4-Methoxy-3-(4-trifluoromethyl-benzyloxy)-benzylsulfanyl]-indan-4-yloxy}-acetic acid methyl ester (compound 78C) The title compound was prepared in the manner analogous to Example 1F using 78B and 12C. MS m/z 373 (M−159). Step 4. Preparation of {7-[4-Methoxy-3-(4-trifluoromethyl-benzyloxy)-benzylsulfanyl]-indan-4-yloxy}-acetic acid (compound 78) The title compound was prepared in the manner analogous to Example 1 using 78C. mp 150-151° C.; IR (KBr) cm−1: 3046, 1722, 1515, 1328, 1232, 1106; 400 MHz 1H NMR (DMSO-d6): δ 12.95 (br(s), 1H), 7.71 (d, 2H, J=8.1 Hz), 7.58 (d, 2H, J=8.1 Hz), 7.03 (d, 1H, J=8.5 Hz), 6.70-6.86 (m, 3H), 6.57 (d, 1H, J=8.5 Hz), 5.01 (s, 2H), 4.61 (s, 2H), 3.89 (s, 2H), 3.69 (s, 3H), 2.75 (t, 2H, J=7.3 Hz), 2.62 (t, 2H, J=7.3 Hz), 1.87 (pentet, 2H); MS m/z 517 (M−1). Anal. Calc'd for C27 H25F3O3S: C, 62.54; H, 4.86; found: C, 62.54; H, 4.71.

Provenance & Evidence