{7-[2-(4-Trifluoromethyl-benzyloxy)-benzylsulfanyl]-indan-4-yloxy}-acetic Acid Methyl Ester → HCID 22280178, compound

HRID 1591569Notes

Reaction equation

HRID 1591569 reaction equation
FC(F)(F)C1C=CC(COC2C=CC=CC=2CO)=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]=[CH:39][C:38]=2[O:43][CH2:44][C:45]2[CH:50]=[CH:49][C:48]([C:51]([F:54])([F:53])[F:52])=[CH:47][CH:46]=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:38]2[CH:39]=[CH:40][CH:41]=[CH:42][C:37]=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 20827069{7-[2-(4-Trifluoromethyl-benzyloxy)-benzylsulfanyl]-indan-4-yloxy}-acetic Acid Methyl Ester2×HCID 22279996[2-(4-Trifluoromethyl-benzyloxy)-phenyl]-methanol

Product 1

HCID 22280178HCID 22280178, compound

Procedure

Preparation of [2-(4-Trifluoromethyl-benzyloxy)-phenyl]-methanol (compound 81A) The title compound was prepared in the manner analogous to Example 14A using 1-bromomethyl-4-trifluoromethyl-benzene and 2-hydroxymethyl-phenol. MS m/z 265 (M-OH). Step 2. Preparation of 1-(4-trifluoromethyl-benzyloxy)-2-chloromethyl-benzene (compound 81B) The title compound was prepared in the manner analogous to Example 3B using 81A. MS m/z 265 (M-Cl). Step 3. Preparation of {7-[2-(4-Trifluoromethyl-benzyloxy)-benzylsulfanyl]-indan-4-yloxy}-acetic acid methyl ester (compound 81C) The title compound was prepared in the manner analogous to Example 1F using 81B and 12C. MS m/z 503 (M+1). Step 4. Preparation of {7-[2-(4-Trifluoromethyl-benzyloxy)-benzylsulfanyl]-indan-4-yloxy}-acetic acid (compound 81) The title compound was prepared in the manner analogous to Example 1 using 81C. mp 150-152° C.; IR (KBr) cm−1: 3074, 3042, 1701, 1324, 1124, 1099; 400 MHz 1H NMR (DMSO-d6): δ 7.58-7.75 (m, 2H), 6.92-7.20 (m, 4H), 6.80 (t, 1H, J=7.5 Hz), 6.51 (d, 1H, J=8.5 Hz), 5.16 (s, 2H), 4.57 (s, 2H), 3.99 (s, 2H), 2.70 (t, 2H, J=7.5 Hz), 2.62 (t, 2H, J=7.5 Hz), 1.80 (pentet, 2H); MS m/z 487 (M−1). Anal. Calc'd for C26H23F3O4S: C, 63.92; H, 4.75; found: C, 63.54; H, 4.52.

Workup

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

Sources & evidence

ORD record
ord-9a400e9c138a4cb59736998a690824b0
Source dataset
uspto-grants-2007_11
Patent number
USRE039916E1

Reaction notes

Loading…