HCID 20827072, compound → HCID 22280130, compound

HRID 1591568Notes

Reaction equation

HRID 1591568 reaction equation
ClC1C=CC(COC2C=C(CO)C=CC=2)=CC=1C(F)(F)F.C[O:23][C:24](=[O:57])[CH2:25][O:26][C:27]1[CH:35]=[CH:34][C:33]([S:36][CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[C:40]([O:44][CH2:45][C:46]3[CH:51]=[CH:50][C:49]([Cl:52])=[C:48]([C:53]([F:56])([F:55])[F:54])[CH:47]=3)[CH:39]=2)=[C:32]2[C:28]=1[CH2:29][CH2:30][CH2:31]2>>[Cl:52][C:49]1[CH:50]=[CH:51][C:46]([CH2:45][O:44][C:40]2[CH:39]=[C:38]([CH:43]=[CH:42][CH:41]=2)[CH2:37][S:36][C:33]2[CH:34]=[CH:35][C:27]([O:26][CH2:25][C:24]([OH:57])=[O:23])=[C:28]3[C:32]=2[CH2:31][CH2:30][CH2:29]3)=[CH:47][C:48]=1[C:53]([F:56])([F:54])[F:55]

Participants

3

Reactant 2

HCID 20827072HCID 20827072, compound2×HCID 22280020HCID 22280020, compound

Product 1

HCID 22280130HCID 22280130, compound

Procedure

Preparation of [3-(4Chloro-3-trifluoromethyl-benzyloxy)-phenyl]-methanol (compound 80A) The title compound was prepared in the manner analogous to Example 14A using 4-bromomethyl-1chloro-2-trifluoromethyl-benzene and 3-hydroxymethyl-phenol. MS m/z 299 (M-OH). Step 2. Preparation of 1-Chloro-4-(3-chloromethyl-phenoxymethyl)-2-trifluoromethyl-benzene (compound 80B) The title compound was prepared in the manner analogous to Example 3B using 80A. MS m/z 299 (M-Cl). Step 3. Preparation of {7-[3-(4-Chloro-3-trifluoromethyl-benzyloxy)-benzylsulfanyl]-indan-4-yloxy}-acetic acid methyl ester (compound 80C) The title compound was prepared in the manner analogous to Example 1F using 80B and 12C. MS m/z 537 (M+1). Step 4. Preparation of {7-[3-(4-Chloro-3-trifluoromethyl-benzyloxy)-benzylsulfanyl]-indan-4-yloxy}-acetic acid (compound 80) The title compound was prepared in the manner analogous to Example 1 using 80C. mp 121-122° C.; IR (KBr) cm−1: 3027, 2584, 1742, 1255, 1129, 1109; 400 MHz 1H NMR (DMSO-d6): δ 12.95 (br(s), 1H), 7.87 (s, 1H), 7.64-7.75 (m, 2H), 7.09-7.19 (m, 1H), 7.01-7.09 (m, 1H), 6.73-6.88 (m, 3H), 6.56 (d, 1H, J=8.5 Hz), 5.06 (s, 2H), 4.60 (s, 2H), 3.95 (s, 2H), 2.74 (t, 2H, J=7.4 Hz), 2.63 (t, 2H, J=7.4 Hz), 1.87 (pentet, 2H); MS m/z 523 (M+1). Anal. Calc'd for C26H22ClF3O4S: C, 59.71; H, 4.24; found: C, 59.45; H, 4.08.

Workup

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

Sources & evidence

ORD record
ord-9572e454388a49b2af9fd2e24809a590
Source dataset
uspto-grants-2007_11
Patent number
USRE039916E1

Reaction notes

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