4'-(Trifluoromethyl)[1,1'-biphenyl]-3-methanol → [7-(4'-Trifluoromethyl-biphenyl-3-ylmethylsulfanyl)-indan-4-yloxy]-acetic Acid

HRID 1591559Notes

Reaction equation

HRID 1591559 reaction equation
FC(F)(F)C1C=CC(C2C=CC=C(CO)C=2)=CC=1.C[O:20][C:21](=[O:51])[CH2:22][O:23][C:24]1[CH:32]=[CH:31][C:30]([S:33][CH2:34][C:35]2[CH:36]=[C:37]([C:41]3[CH:46]=[CH:45][C:44]([C:47]([F:50])([F:49])[F:48])=[CH:43][CH:42]=3)[CH:38]=[CH:39][CH:40]=2)=[C:29]2[C:25]=1[CH2:26][CH2:27][CH2:28]2>>[F:50][C:47]([F:48])([F:49])[C:44]1[CH:45]=[CH:46][C:41]([C:37]2[CH:38]=[CH:39][CH:40]=[C:35]([CH2:34][S:33][C:30]3[CH:31]=[CH:32][C:24]([O:23][CH2:22][C:21]([OH:51])=[O:20])=[C:25]4[C:29]=3[CH2:28][CH2:27][CH2:26]4)[CH:36]=2)=[CH:42][CH:43]=1

Participants

3

Reactant 2

HCID 144680034'-(Trifluoromethyl)[1,1'-biphenyl]-3-methanolHCID 20827075[7-(4'-Trifluoromethyl-biphenyl-3-ylmethylsulfanyl)-indan-4-yloxy]-acetic acid methyl ester2×

Product 1

HCID 22280056[7-(4'-Trifluoromethyl-biphenyl-3-ylmethylsulfanyl)-indan-4-yloxy]-acetic Acid

Procedure

Preparation of (4′-Trifluoromethyl-biphenyl-3-yl)-methanol (compound 48A) The title compound was prepared in the manner analogous to Example 3A with 1-bromo-4-trifluoromethyl-benzene and 3-(hydroxymethyl)phenyl boronic acid. MS m/z 251 (M−1). Step 2. Preparation of 3-Chloromethyl-4′-trifluoromethyl-biphenyl (compound 48B) The title compound was prepared in the manner analogous to Example 3B using 48A. MS m/z 236 (M+1-Cl). Step 3. Preparation of [7-(4′-Trifluoromethyl-biphenyl-3-ylmethylsulfanyl)-indan-4-yloxy]-acetic acid methyl ester (compound 48C) The title compound was prepared in the manner analogous to Example 1F using 12C and 48B. MS m/z 473 (M+1). Step 4. Preparation of [7-(4′-Trifluoromethyl-biphenyl-3-ylmethylsulfanyl)-indan-4-yloxy]-acetic acid (compound 48) The title compound was prepared in the manner analogous to Example 1 using 48C. 400 MHz 1H NMR (DMSO-d6) δ 12.96 (br(s), 1H), 7.75 (d, 2H, J=8.3 Hz), 7.67 (d, 2H, J=8.1 Hz), 7.52 (m, 1H), 7.37 (t, 1H, J=7.6 Hz), 7.29 (m, 2H), 7.13 (d, 1H, J=8.5 Hz), 6.61 (d, 1H, J=8.5 Hz), 4.63 (s, 2H), 4.05 (s, 2H), 2.71 (t, 2H), 2.58 (t, 2H), 1.81 (m, 2H). MS m/z 459 (M+1).

Workup

  1. customwas prepared in the manner analogous to Example 3B

Sources & evidence

ORD record
ord-83d94e1bfd01425fa69ec46674a57a18
Source dataset
uspto-grants-2007_11
Patent number
USRE039916E1

Reaction notes

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