HCID 20827096, compound → HCID 22280077, compound

HRID 1591566Notes

Reaction equation

HRID 1591566 reaction equation
COC1C=CC(CO)=CC=1OCC1C=CC(C(F)(F)F)=CC=1.C[O:24][C:25](=[O:59])[CH2:26][O:27][C:28]1[CH:36]=[CH:35][C:34]([S:37][CH2:38][C:39]2[CH:44]=[CH:43][C:42]([O:45][CH3:46])=[C:41]([O:47][CH2:48][C:49]3[CH:54]=[CH:53][C:52]([C:55]([F:58])([F:57])[F:56])=[CH:51][CH:50]=3)[CH:40]=2)=[C:33]2[C:29]=1[CH2:30][CH2:31][CH2:32]2>>[CH3:46][O:45][C:42]1[CH:43]=[CH:44][C:39]([CH2:38][S:37][C:34]2[CH:35]=[CH:36][C:28]([O:27][CH2:26][C:25]([OH:59])=[O:24])=[C:29]3[C:33]=2[CH2:32][CH2:31][CH2:30]3)=[CH:40][C:41]=1[O:47][CH2:48][C:49]1[CH:54]=[CH:53][C:52]([C:55]([F:58])([F:56])[F:57])=[CH:51][CH:50]=1

Participants

3

Reactant 2

HCID 20827096HCID 20827096, compound2×HCID 22280080HCID 22280080, compound

Product 1

HCID 22280077HCID 22280077, compound

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-3650897eafb647198392f1892a340792
Source dataset
uspto-grants-2007_11
Patent number
USRE039916E1

Reaction notes

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