HCID 20827047, compound → HCID 10288804, compound
Reaction equation
FC(F)(F)OC1C=C(C2C=CC=C(CO)C=2)C=CC=1.C[O:21][C:22](=[O:53])[CH2:23][O:24][C:25]1[CH:30]=[C:29]([O:31][CH3:32])[C:28]([S:33][CH2:34][C:35]2[CH:36]=[C:37]([C:41]3[CH:46]=[CH:45][CH:44]=[C:43]([O:47][C:48]([F:51])([F:50])[F:49])[CH:42]=3)[CH:38]=[CH:39][CH:40]=2)=[CH:27][C:26]=1[CH3:52]>>[CH3:32][O:31][C:29]1[C:28]([S:33][CH2:34][C:35]2[CH:36]=[C:37]([C:41]3[CH:46]=[CH:45][CH:44]=[C:43]([O:47][C:48]([F:51])([F:50])[F:49])[CH:42]=3)[CH:38]=[CH:39][CH:40]=2)=[CH:27][C:26]([CH3:52])=[C:25]([CH:30]=1)[O:24][CH2:23][C:22]([OH:53])=[O:21]Participants
Procedure
Preparation of (3′-Trifluoromethoxy-biphenyl-3-yl)-methanol (compound 16A) The title compound was prepared in the manner analogous to Example 3A using 3-hydroxymethylphenylboronic acid and 1-bromo-3-trifluoromethoxy-benzene. MS m/z 251 (M−1). Step 2. Preparation of 3-Chloromethyl-3′-trifluoromethoxy-biphenyl (compound 16B) The title compound was prepared in the manner analogous to Example 3B using 16A. MS m/z 251 (M−1). Step 2. Preparation of [5-Methoxy-2-methyl-4-(3′-trifluoromethoxy-biphenyl-3-ylmethylsulfanyl)-phenoxy]-acetic acid methyl ester (compound 16C) The title compound was prepared in the manner analogous to Example 1F using 16B and 1D. MS m/z 491 (M−1). Step 4. Preparation of [5-Methoxy-2-methyl-4-(3′-trifluoromethoxy-biphenyl-3-ylmethylsulfanyl)-phenoxy]-acetic acid (compound 16) The title compound was prepared in the manner analogous to Example 1 using 16C. mp 92-94° C.; 400 MHz 1H NMR (DMSO-d6) δ 12.96 (br(s), 1H), 7.55-7.24 (m, 8H), 7.01 (s, 1H), 6.52 (s, 1H), 4.68 (s, 2H), 4.03 (s, 2H), 3.72 (s, 3H), 1.99 (s, 3H); MS m/z 479 (M+1).
Workup
- customwas prepared in the manner analogous to Example 3B
Sources & evidence
- ORD record
- ord-63da409ee3e34329a77d5d548ab414fc
- Source dataset
- uspto-grants-2007_11
- Patent number
- USRE039916E1
Reaction notes
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