5-(3-Chloro-4-propoxyphenyl)-3-(3-iodo-4-isopropoxyphenyl)-1,2,4-oxadiazole → HCID 136359939, compound

HRID 717700Notes

Reaction equation

HRID 717700 reaction equation
[CH2:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[O:15][N:14]=[C:13]([C:16]3[CH:21]=[CH:20][C:19]([O:22]C(C)C)=[C:18]([I:26])[CH:17]=3)[N:12]=2)=[CH:7][C:6]=1[O:27][CH3:28])[CH2:2][CH3:3].ClC1C=C(C2ON=C(C3C=CC(OC(C)C)=C(I)C=3)N=2)C=CC=1OCCC>>[CH2:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[O:15][N:14]=[C:13]([C:16]3[CH:21]=[CH:20][C:19]([OH:22])=[C:18]([I:26])[CH:17]=3)[N:12]=2)=[CH:7][C:6]=1[O:27][CH3:28])[CH2:2][CH3:3]

Participants

3

Reactant 2

HCID 666149435-(3-Chloro-4-propoxyphenyl)-3-(3-iodo-4-isopropoxyphenyl)-1,2,4-oxadiazoleHCID 68002070HCID 68002070, compound

Product 1

HCID 136359939HCID 136359939, compoundYield 80%

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 80% yield, as creamy solid. 1H-NMR (CDCl3) 8.48 (d, 1H, J=1.98 Hz); 8.04 (dd, 1H, J=8.46, 1.98 Hz); 7.7 (dd, 1H, J=8.43, 2.01 Hz); 7.65 (d, 1H, J=1.95 Hz); 7.07 (d, 1H, J=8.49 Hz); 6.97 (d, 1H), J=8.46 Hz); 5.63 (s, 1H); 4.06 (t, 2H, J=6.8 Hz); 4.02 (s, 3H); 1.94-1.87 (m, 2H); 1.06 (t, 3H, J=7.41 Hz).

Sources & evidence

ORD record
ord-64e12ca7440248a6b100d3e9c546ed44
Source dataset
uspto-grants-2015_11
Patent number
US09193716B2

Reaction notes

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