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

HRID 2046116Notes

Reaction equation

HRID 2046116 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[O:14][N:13]=[C:12]([C:15]3[CH:20]=[CH:19][C:18]([O:21]C(C)C)=[C:17]([I:25])[CH:16]=3)[N:11]=2)=[CH:6][CH:5]=1)[CH3:2].ClC1C=C(C2ON=C(C3C=CC(OC(C)C)=C(I)C=3)N=2)C=CC=1OCCC>>[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[O:14][N:13]=[C:12]([C:15]3[CH:20]=[CH:19][C:18]([OH:21])=[C:17]([I:25])[CH:16]=3)[N:11]=2)=[CH:6][CH:5]=1)[CH3:2]

Participants

3

Reactant 2

HCID 666149435-(3-Chloro-4-propoxyphenyl)-3-(3-iodo-4-isopropoxyphenyl)-1,2,4-oxadiazoleHCID 666149895-(4-Ethoxyphenyl)-3-(3-iodo-4-isopropoxyphenyl)-1,2,4-oxadiazole

Product 1

HCID 1363599424-(5-(4-Ethoxyphenyl)-1,2,4-oxadiazol-3-yl)-2-iodophenolYield 87%

Procedure

When the product of Step A was substituted for 5-(3-chloro-4-propoxyphenyl)-3-(3-iodo-4-isopropoxyphenyl)-1,2,4-oxadiazole in Example 36, Step C, the similar procedure afforded the title compound in 87% yield, as white solid. 1H-NMR (CDCl3) 8.47 (d, 1H, J=1.95 Hz); 8.11 (d, 2H, J=8.94 Hz); 8.03 (dd, 1H, J=8.46, 2.01 Hz); 7.07 (d, 2H, J=8.49 Hz); 4.11 (q, 2H, J=6.96, 13.98 Hz); 1.45 (t, 3H, J=6.96 Hz).

Sources & evidence

ORD record
ord-837624c0fb004f108aea3cbf762c2245
Source dataset
uspto-grants-2013_11
Patent number
US08592399B2

Reaction notes

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