{7-[3-(5-Trifluoromethyl-pyridin-2-yl)-benzylsulfanyl]-indan-4-yloxy}-acetic acid methyl ester → {7-[3-(5-Trifluoromethyl-pyridin-2-yl)-benzylsulfanyl]-indan-4-yloxy}-acetic acid

HRID 1591562Notes

Reaction equation

HRID 1591562 reaction equation
FC(F)(F)C1C=CC(C2C=C(CO)C=CC=2)=NC=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:40]=[CH:39][CH:38]=[C:37]([C:41]3[CH:46]=[CH:45][C:44]([C:47]([F:50])([F:49])[F:48])=[CH:43][N:42]=3)[CH:36]=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:36]=[C:35]([CH:40]=[CH:39][CH:38]=2)[CH2:34][S:33][C:30]2[CH:31]=[CH:32][C:24]([O:23][CH2:22][C:21]([OH:51])=[O:20])=[C:25]3[C:29]=2[CH2:28][CH2:27][CH2:26]3)=[N:42][CH:43]=1

Participants

3

Reactant 2

HCID 20827077{7-[3-(5-Trifluoromethyl-pyridin-2-yl)-benzylsulfanyl]-indan-4-yloxy}-acetic acid methyl ester2×HCID 222800643-(3-(Trifluoromethyl)pyridin-2-YL)benzyl alcohol

Product 1

HCID 22280108{7-[3-(5-Trifluoromethyl-pyridin-2-yl)-benzylsulfanyl]-indan-4-yloxy}-acetic acid

Procedure

Preparation of [3-(5-Trifluoromethyl-pyridin-2-yl)-phenyl]-methanol (compound 53A) The title compound was prepared in the manner analogous to Example 3A using 3-(hydroxymethyl)phenyl boronic acid and 2-chloro-5-trifluoromethyl-pyridine. MS m/z 253 (M+1). Step 2. Preparation of 2-(3-Chloromethyl-phenyl)-5-trifluoromethyl-pyridine (compound 53B) The title compound was prepared in the manner analogous to Example 3B using 53A. MS m/z 237 (M+1-Cl). Step 3. Preparation of {7-[3-(5-Trifluoromethyl-pyridin-2-yl)-benzylsulfanyl]-indan-4-yloxy}-acetic acid methyl ester (compound 53C) The title compound was prepared in the manner analogous to Example 1F using 12C and 53B. MS m/z 474 (M+1). Step 4. Preparation of {7 -[3-(5-Trifluoromethyl-pyridin-2-yl)-benzylsulfanyl]-indan-4-yloxy}-acetic acid (compound 53) The title compound was prepared in the manner analogous to Example 1 using 53C. 400 MHz 1H NMR (DMSO-d6) δ 8.98 (m, 1H), 8.23 (dd, 1H, J=1.7 Hz, J′=8.5 Hz), 7.99 (m, 2H), 7.87 (s, 1H), 7.39 (t, 1H, J=7.6 Hz), 7.33 (m, 1H), 7.11 (d, 1H, J=8.5 Hz), 6.58 (d, 1H, J=8.5 Hz), 4.61 (s, 2H), 4.08 (s, 2H), 2.70 (t, 2H, J=7.3 Hz), 2.63 (t, 2H, J=7.6 Hz), 1.84 (m, 2H). MS m/z 460 (M+1).

Workup

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

Sources & evidence

ORD record
ord-fc9d2ad335e246209c8f2043b1fc8c3e
Source dataset
uspto-grants-2007_11
Patent number
USRE039916E1

Reaction notes

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