5-(3-Chloro-4-propoxyphenyl)-3-(3-iodo-4-isopropoxyphenyl)-1,2,4-oxadiazole → 5-Chloro-2-iodo-4-(5-(4-propylphenyl)-1,2,4-oxadiazol-3-yl)phenol

HRID 2046119Notes

Reaction equation

HRID 2046119 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8]C(C)C)[C:5]([I:12])=[CH:4][C:3]=1[C:13]1[N:17]=[C:16]([C:18]2[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][CH3:26])=[CH:20][CH:19]=2)[O:15][N:14]=1.ClC1C=C(C2ON=C(C3C=CC(OC(C)C)=C(I)C=3)N=2)C=CC=1OCCC>>[Cl:1][C:2]1[C:3]([C:13]2[N:17]=[C:16]([C:18]3[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][CH3:26])=[CH:20][CH:19]=3)[O:15][N:14]=2)=[CH:4][C:5]([I:12])=[C:6]([OH:8])[CH:7]=1

Participants

3

Reactant 2

HCID 666149435-(3-Chloro-4-propoxyphenyl)-3-(3-iodo-4-isopropoxyphenyl)-1,2,4-oxadiazoleHCID 666149563-(2-Chloro-5-iodo-4-isopropoxyphenyl)-5-(4-propylphenyl)-1,2,4-oxadiazole

Product 1

HCID 1363599435-Chloro-2-iodo-4-(5-(4-propylphenyl)-1,2,4-oxadiazol-3-yl)phenolYield 55%

Procedure

When the product of Step B was substituted for 5-(3-chloro-4-propoxy phenyl)-3-(3-iodo-4-isopropoxyphenyl)-1,2,4-oxadiazole in Example 36, Step C, the similar procedure afforded the title compound in 55% yield, as creamy solid. 1H NMR (CDCl3) 8.37 (s, 1H); 8.10 (d, 2H, J=8.25 Hz); 7.33 (d, 2H, J=8.25 Hz); 7.16 (s, 1H); 5.78 (b, 1H); 2.67 (t, 2H, J=7.38 Hz); 1.74-1.56 (m, 2H); 0.96 (t, 3H, J=7.32 Hz).

Sources & evidence

ORD record
ord-69d90058c52a46adb22b1092b4b53624
Source dataset
uspto-grants-2013_11
Patent number
US08592399B2

Reaction notes

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