{7-[3-(4-Trifluoromethyl-benzyloxy)-benzylsulfanyl]-indan-4-yloxy}-acetic acid methyl ester → HCID 22280149, compound

HRID 1591567Notes

Reaction equation

HRID 1591567 reaction equation
FC(F)(F)C1C=CC(COC2C=C(CO)C=CC=2)=CC=1.C[O:22][C:23](=[O:55])[CH2:24][O:25][C:26]1[CH:34]=[CH:33][C:32]([S:35][CH2:36][C:37]2[CH:42]=[CH:41][CH:40]=[C:39]([O:43][CH2:44][C:45]3[CH:50]=[CH:49][C:48]([C:51]([F:54])([F:53])[F:52])=[CH:47][CH:46]=3)[CH:38]=2)=[C:31]2[C:27]=1[CH2:28][CH2:29][CH2:30]2>>[F:53][C:51]([F:52])([F:54])[C:48]1[CH:49]=[CH:50][C:45]([CH2:44][O:43][C:39]2[CH:38]=[C:37]([CH:42]=[CH:41][CH:40]=2)[CH2:36][S:35][C:32]2[CH:33]=[CH:34][C:26]([O:25][CH2:24][C:23]([OH:55])=[O:22])=[C:27]3[C:31]=2[CH2:30][CH2:29][CH2:28]3)=[CH:46][CH:47]=1

Participants

3

Reactant 2

HCID 20827074{7-[3-(4-Trifluoromethyl-benzyloxy)-benzylsulfanyl]-indan-4-yloxy}-acetic acid methyl ester2×HCID 22280195[3-(4-Trifluoromethyl-benzyloxy)-phenyl]-methanol

Product 1

HCID 22280149HCID 22280149, compound

Procedure

Preparation of [3-(4-trifluoromethyl-benzyloxy)-phenyl]-methanol (compound 79A) The title compound was prepared in the manner analogous to Example 14A using 1-bromomethyl-4-trifluoromethyl-benzene and 3-hydroxymethyl-phenol. MS m/z 265(M-OH). Step 2. Preparation of 1-(4-trifluoromethyl-benzyloxy)-3-chloromethyl-benzene (compound 79B) The title compound was prepared in the manner analogous to Example 3B using 79A. MS m/z 265 (M-Cl). Step 3. Preparation of {7-[3-(4-Trifluoromethyl-benzyloxy)-benzylsulfanyl]-indan-4-yloxy}-acetic acid methyl ester (compound 79C) The title compound was prepared in the manner analogous to Example 1F using 79B and 12C. MS m/z 503 (M+1). Step 4. Preparation of {7-[3-(4-Trifluoromethyl-benzyloxy)-benzylsulfanyl]-indan-4-yloxy}-acetic acid (compound 79) The title compound was prepared in the manner analogous to Example 1 using 79C. mp 145-146° C.; IR (KBr) cm−1: 3076, 3028, 1705, 1318, 1232, 1109; 400 MHz 1H NMR (DMSO-d6): δ 12.94 (br(s), 1H), 7.71 (d, 2H, J=8.2 Hz), 7.59 (d, 2H, J=8.0 Hz), 7.10-7.19 (m, 1H), 7.05 (d, 1H, J=8.5 Hz), 6.75-6.86 (m, 4H), 6.58 (d, 1H, J=8.5 Hz), 5.08 (s, 2H), 4.61 (s, 2H), 3.95 (s, 2H), 2.75 (t, 2H, J=7.5 Hz), 2.64 (t, 2H, J=7.5 Hz), 1.88 (pentet, 2H); MS m/z 487 (M−1). Anal. Calc'd for C26H23F3O4S: C, 63.92; H, 4.75; found: C, 63.78; H, 4.53.

Workup

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

Sources & evidence

ORD record
ord-073d03cfa7ec47e5b7c6864793c99885
Source dataset
uspto-grants-2007_11
Patent number
USRE039916E1

Reaction notes

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