5-(3,4-Diethoxyphenyl)-3-(1H-indol-4-yl)-1,2,4-oxadiazole → 3-(Indolin-4-yl)-5-(6-propylpyridin-3-yl)-1,2,4-oxadiazole

HRID 710475Notes

Reaction equation

HRID 710475 reaction equation
[NH:1]1[C:9]2[C:4](=[C:5]([C:10]3[N:14]=[C:13]([C:15]4[CH:16]=[N:17][C:18]([CH2:21][CH2:22][CH3:23])=[CH:19][CH:20]=4)[O:12][N:11]=3)[CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.C(OC1C=C(C2ON=C(C3C=CC=C4C=3C=CN4)N=2)C=CC=1OCC)C>>[NH:1]1[C:9]2[C:4](=[C:5]([C:10]3[N:14]=[C:13]([C:15]4[CH:16]=[N:17][C:18]([CH2:21][CH2:22][CH3:23])=[CH:19][CH:20]=4)[O:12][N:11]=3)[CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 251102975-(3,4-Diethoxyphenyl)-3-(1H-indol-4-yl)-1,2,4-oxadiazoleHCID 667262143-(1H-indol-4-yl)-5-(6-propylpyridin-3-yl)-1,2,4-oxadiazole

Product 1

HCID 667262803-(Indolin-4-yl)-5-(6-propylpyridin-3-yl)-1,2,4-oxadiazoleYield 19%

Procedure

When the product of Step C was substituted for 5-(3,4-diethoxyphenyl)-3-(1H-indol-4-yl)-1,2,4-oxadiazole in Example 34, Step C, the similar process afforded the title compound in 19% yield, as creamy solid. 1H-NMR (CDCl3) 1.01 (m, 3H); 1.7-1.9 (m, 2H); 2.87 (m, 2H); 3.46 (tr, 2H, J=9 Hz); 3.64 (tr, 2H, J=9 Hz); 3.9 (broad s, 1H); 6.76 (d, 1H, J=6 Hz); 7.16 (m, 1H); 7.33 (d, 1H, J=9 Hz); 7.53 (dd, 1H, J=2, 9 Hz); 8.35 (dd, 1H, 3, 9 Hz); 9.33 (d, 1H, J=3 Hz).

Sources & evidence

ORD record
ord-d0aa3e61ee0a4c18854775ba345a2dbe
Source dataset
uspto-grants-2015_11
Patent number
US09181182B2

Reaction notes

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